The city of Chicago is known for a variety of things — culinary expertise, immense architecture, and world-class theatre. Chicago, in addition, should not be forgotten as a city with amazing shopping.

The Magnificent Mile and State Street are bustling downtown areas that undoubtedly have something for everyone. For those looking for luxury and upscale options, we’ve got that too. Check out these boutique shopping guides for the next time you’re in one of our neighborhoods.

My friends and I spend a lot of time at these places. We can thank these stores for filling up our closets and giving us a place to hang out, walk around, and appreciate the city. The stores we hold closest to our hearts, though, are the ones off the beaten path.

We gravitate toward the locally owned, singular boutiques that can only be found in Chicago. As we’ve become regulars, talked to store owners, and invested in these places, we unraveled an extremely tight-knit community of people who care about elevating Chicago as a fashion city. If you also find yourself gravitating off the beaten path, here’s your guide to the best hidden gems in the city to go shopping.

Notre

My journey to finding underground stores started around four years ago when I was visiting Chicago with a group of friends. I was doing research for the trip and stumbled upon a GQ article that listed the 100 best clothing stores in the world. Notre really struck a chord with me, and to this day, it is still my favorite place in Chicago.

Notre is a masterclass in beautiful architecture. Before opening, the brand collaborated with architecture firm Norman Kelley to renovate the interior of a 100-year-old building in Chicago’s Fulton Market. Before even seeing any product in the store, the entrance to the building is an experience in and of itself.

Notre is a leader in collaborating and giving back to its community. They recently hosted events surrounding the release of the Jordan 1 OG x Virgil Abloh Archive, including a community collage workshop with a local artist and an art supplies donation drive.

I could go on about how amazing the store is, but I’d rather let the space speak for itself in this lookbook.

SVRN

Close to Notre in proximity but far from it in tonality — SVRN is proudly and boldly brutalist.

What you will find on the shelves is not much different than what you will find on the patrons. Other than my brother and I, the only other customer in the store was a man wearing entirely Rick Owens.

I want people to visit SVRN because it truly feels like you’re entering a different world when you step through the doors — think the Oakley headquarters or the mansion in Ex Machina.

The space was created by WGNB, a South Korean-based firm, who bring a unique design perspective: “While the western perspective looks at the object itself, the eastern perspective rather focuses on the surrounding relationship of the object.”

It’s about the experience of shopping, rather than the act of shopping. SVRN has truly curated a place for lovers of art and artists… and those who love Rick Owens.

Goody Vault

Goody Vault curates vintage the way vintage is supposed to be curated. In my conversations with Manny, the owner of the studio and workshop, he emphasized the importance of authenticity.

At the intersection of North, Damen, and Milwaukee Avenues is a bustling area of Wicker Park known as the Six Corners. This is where you’ll find the Flat Iron Arts Building, a long-standing community hub where the independent art scene thrives. It’s a beautiful juxtaposition of a historic building providing a space for current artists to affordably occupy a studio.

Manny occupies one of these studios to sell his vintage collection. He lines the walls with his most prized possessions and fills up racks with other unique pieces. His collection is full of clothes dating back to the ‘40s, ‘50s, and ‘60s — varsity knit sweaters from high schools, softball jerseys from God-knows-what beer league, and even real military garments.

I was drawn to Manny’s confidence in his own taste and passion for promoting authenticity. He truly believes in curating a collection of clothes that are unique, not just what he knows are going to sell.

Ford General

Ford General is the perfect example of why the people who operate these businesses make them so special. Located in the Old Town neighborhood, Ford General is run by Patrick Ford, who has an overwhelming passion for luxury menswear.

The passion extends to everyone who works at the store — they’re experts in their field and they love educating you on it. My roommates and I live within walking distance of the store, and we frequently saunter over on Friday evenings after work. It’s cozy inside, and every once in a while, you might catch Patrick wearing some luxury Italian denim.

The Silver Room

The Silver Room was founded by Eric Williams nearly 20 years ago. It was originally created to be a space for local artists and vendors to sell their products in a storefront. It has since grown to be a community that hosts events for all kinds of different artists. You can find a schedule of events on their social channels, including open mic nights, wellness classes, and concerts.

The Silver Room has become a cornerstone of the Hyde Park neighborhood on the city’s South Side and is looking forward to hosting its annual block party this summer. What started as a small gathering of family and friends and has turned into one of Chicago’s largest celebrations of Black culture. This year, the party will be held at The Salt Shed on July 18.

Shady Rest

Shady Rest is a small store in the historic Pilsen neighborhood carrying the torch for lovers of physical media. In Pilsen, 18th Street is known as a hub for local shops and vintage stores. Among the many storefronts in the neighborhood, Shady Rest really stuck out to me.

This place celebrates anything and everything vintage. To go along with your records, you could also purchase a record player and speakers. There’s also a shelf dedicated to old clocks and radios. On your way out, don’t forget to check out the camcorders and film rolls in the glass cabinet. Shady Rest has a little bit of everything. I’d encourage anyone who likes records, books, and old household items to check out Shady Rest.

Round 2

Looking back on the hypebeast era gives me profound feelings about my teenage years. It is equally nostalgic as it was chaotic. For as meteoric as the hypebeast culture rise was, the fall was even more dramatic. Streetwear is still very much alive, but not like it was in the mid 2010s. The people we can thank for pioneering and accelerating the movement are still operating today, but in a much more limited capacity.

Round 2 was originally a storefront in Richmond, Virginia, where they bought, sold, and curated streetwear. Around the mid 2010’s, this was the gold standard for streetwear/resale culture. They gained a cult following on YouTube. My good friend, who was born and raised in Scotland, used to watch the Round 2 videos back in Glasgow. That’s how far the Round 2 influence reached at its peak.

Over the next half-decade, replica stores popped up all over the country, and the resale market grew oversaturated. The original store has closed its doors, but the last remaining Round 2 is still open in Chicago, operated by one of the original founders. I still enjoy shopping at Round 2 and basking in the nostalgic feelings of the hypebeast-era golden days.

The annual James Beard Awards recognize the best and the brightest of the nation’s dining scene. These prestigious accolades honor not only chefs and restaurants that demonstrate excellence in quality, but those who contribute positively to their communities.

As the official home of the James Beard Awards through 2028, Chicago also has a fair share of award contenders this year — popular spots like Monteverde, Feld, and Cariño are nominated for top awards.

Check out the full list of Chicago nominees below. The winners will be announced at the 36th annual James Beard Restaurant and Chef Awards Ceremony on June 15, 2026 at the Lyric Opera of Chicago.

James Beard Award 2026 nominees

Emerging Chef

• Bailey Sullivan of Monteverde Restaurant & Pastificio

Best Chef, Great Lakes

• Norman Fenton of Cariño
• Jacob Potashnick of Feld

James Beard Media Awards: Foodways
This award recognizes the importance of culture and history in food journalism. Entries in this category explore the connection between what we eat and who we are, with an emphasis on reporting.

• “The hunt for the bean pie street sellers of legend, and how this dessert is a symbol of liberation for many Black Muslims” — Ahmed Ali Akbar, Chicago Tribune

James Beard Award 2026 Chicago semi-finalists

Outstanding Restaurateur
A restaurateur who uses their establishment(s) as a vehicle for building community, demonstrates creativity in entrepreneurship, and integrity in restaurant operations.

• Frank Callero, Joe Flamm, and Steven Zaleski, Day Off Group (Rose Mary, il Carciofo, and BLVD Steakhouse)

Outstanding Chef
A chef who sets high culinary standards and has served as a positive example for other food professionals.

• Diana Davila, Mi Tocaya Antojeria
• Zachary Engel, Galit

Outstanding Restaurant
A restaurant that demonstrates consistent excellence in food, atmosphere, hospitality, and operations.

• EL Ideas
• Kasama

Emerging Chef
A chef who displays exceptional talent, character, and leadership ability, and who is likely to make a significant impact in years to come.

• Nicolai Mlodinow, Class Act
• Bailey Sullivan, Monteverde Restaurant & Pastificio

Best New Restaurant
A restaurant that already demonstrates excellence in cuisine, seems likely to make a significant impact in years to come, and demonstrates consistent excellence in food, atmosphere, hospitality, and operations.

• Nadu
• Nic & Junior’s

Outstanding Pastry Chef or Baker
A pastry chef or baker who makes desserts, pastries, or breads and demonstrated exceptional skills.

• Courtney Kenyon-Snider, Obélix

Outstanding Hospitality
A restaurant, bar, or other food and drinking establishment that fosters a sense of hospitality among its customers and staff that serves as a beacon for the community and demonstrates consistent excellence in food, atmosphere, hospitality, and operations.

• Daisies

Outstanding Wine and Other Beverages Program
A restaurant that demonstrates exceptional care and skill in the pairing of wine and other beverages with food.

• Brasero

Outstanding Bar
A bar that demonstrates consistent excellence in curating a selection or in the preparation of drinks, along with outstanding atmosphere, hospitality, and operations.

• Hopleaf

Outstanding Professional in Cocktail Service
A service professional who demonstrates creativity and consistency in excellence, innovation, and hospitality; is making efforts to create a sustainable work culture; and has served as an exceptional example or mentor for other beverage professionals.

• Christopher Marty, Best Intentions

Best Chef: Great Lakes
Chefs who set high standards in their culinary skills and leadership abilities and who are making efforts to help create a sustainable work culture in their respective regions.

• Thai Dang, HaiSous
• Danny Espinoza, Santa Masa Tamaleria
• Norman Fenton, Cariño
• Christopher Jung and Erling Wu-Bower, Maxwells Trading
• Mari Katsumura and Adam Sindler, SHŌ
• Nick Kleutsch and James Sanders, Sanders BBQ Supply Co.
• Rishi Kumar and Zubair Mohajir, Mirra
• Ben Lustbader and Sarah Mispagel, Loaf Lounge
• Jacob Potashnick, Feld

Check out all the Chicago James Beard Award winners and catch the this year’s ceremony on June 15, 2026!

Chicago has long been known for its world-class shopping. While The Magnificent Mile usually gets much of the (well-deserved!) glory, the city’s fashion destinations extend far beyond Michigan Avenue, especially when it comes to independent designers.

Home to multiple top-tier fashion schools and a thriving creative community, Chicago’s fashion scene has been steadily growing, cultivating a unique mix of talented individuals who have chosen to build their brands right here in the city.

If you’re looking for unique Chicago-based brands, we’ve put together a guide to standout stores that showcase locally designed goods. Some of the designers are renowned for dressing famous faces, others are under-the-radar local favorites — and many can be found only in Chicago.

While no single roundup could ever capture the city’s fashion talent, this selection of shops should give a taste of how diverse and dynamic Chicago style really is.

Chicago boutiques with locally designed brands

Maria Pinto

Just a short hop from The Mag Mile, you’ll find Maria Pinto’s boutique.

The famous designer has worked with luminaries like Michelle Obama and Oprah, but her clothes are perfect for any woman looking for sophisticated fashion.

Maria’s designs are defined by her striking architectural silhouettes and pintuck details that add interest to statement pieces and basics alike.

Seasonal patterns and colors are often inspired by her travels. And these clothes are as easy to wear as they are beautiful — her signature eco-friendly fabric doesn’t wrinkle and can be thrown in the washing machine.

Swaby

Chicago designer Swaby just opened a store in New York City, but her flagship remains right here in the city’s Wicker Park neighborhood.

The Project Runway Canada star sews many of the items in her store herself. Each of her designs is embellished with details like her signature sculptural “bubbles” and grosgrain overlays that elevate them to works of art.

Should you ever decide that you want to change something on your Swaby item, perhaps take in a sleeve, shorten a hem, or alter the neckline, Shernett Swaby offers free lifetime alterations — because she truly wants you to love it forever.

Azeeza

Although this brand is sold at luxury department stores nationwide, Azeeza’s intimate flagship is located right here in the 900 North Michigan Shops.

Born and raised in Chicago, Azeeza Khan designs ethically produced women’s wear that embraces modern femininity with sweeping silhouettes and luxe silks.

The brand has collaborated with everyone from Nike to CB2 and dressed celebrities like Beyoncé and Barbra Streisand. So, if you’re looking for some statement dresses to make you feel like a star this summer, you’ve found your store!

Production Mode

Carrying a well-curated selection of designers from Chicago and beyond, this multi-brand store in the North Center neighborhood is a haven for those who love independent designers.

Production Mode’s own line by local designer Jamie Hayes focuses on small-batch production and high-quality garments.

She often collaborates with other Chicago artisans and artists, such as The Weaving Mill and Horween Leather Company, which preserve the heritage of Chicago’s textile past.

Pro tip: Make sure to follow the boutique on Instagram because they often host events, workshops, and pop-ups with local designers.

Leaders 1354

You can’t talk about Chicago style without talking about streetwear.

One of the city’s original streetwear stores, Leaders 1354 is located in the hip West Loop neighborhood — and it’s attracted fashionable celebs like Chance the Rapper and Dwyane Wade.

From perfectly slouchy hoodies and branded leather jackets to the hats and sneakers that put the finishing touch on your look, you’ll find it all here.

But more than that, you’ll find a store that has a real mission — to promote creativity and leadership in their community through mentorship.

Niczka

This Chicago brand is opening a new store concept in June.

The brand, which creates both men’s and women’s wear, has been nominated for national fashion awards and been showcased on television.

Niczka is particularly known for their showstopping “light avant garde” style and unique pieces like sculptural puffer coats and capes.

If you make a purchase at Niczka, you’re sure to walk away with a unique item that will leave people asking where you bought it.

The Silver Room

The Silver Room is more than a store — it’s a neighborhood institution.

For almost 30 years, the boutique has created both a curated shopping experience and meaningful cultural events that celebrate the Chicago spirit. Their annual Silver Room Block Party is a highly anticipated summer tradition that spotlights local music, art, and community.

Whether you’re looking for a Chicago-inspired souvenir to commemorate your trip or want to purchase a pair of stylish sneakers from local designer and Pulitzer Prize-winning investigative journalist Yohance Lacour, this is your spot.

Dearborn Denim

With denim in their name, you won’t be surprised that this is a great place to find a pair of jeans.

Dearborn Denim, a family-owned and operated small business in the Andersonville neighborhood, specializes in classic denim that is designed, cut, sewn, and finished right in their Chicago factory.

In addition to their signature denim items, they also design jackets, tops, sweatshirts, and a selection of leather accessories.

While they offer both men’s and women’s clothing, their men’s department is particularly strong. Browse multiple styles, fits, and fabrics across a huge selection of ethically made pants at a great price.

Barbara Bates

Another Chicago icon, Barbara Bates has dressed everyone from Michael Jordan to Whitney Houston.

This year is a particularly special time to visit Barbara’s store. She’s celebrating 40 years of business and capping it off with a fashion show at the Obama Presidential Center this October.

Barbara loves designing in bold colors and bright patterns and often includes leather in her creations. If you’re looking for something that particularly encapsulates her style, keep an eye out for her hand-painted graffiti bags!

Every great road trip begins with a spark, and in the Midwest, that spark is Chicago. Spend time immersed in the city’s museums, lakefront, and neighborhoods, then set out to see what lies beyond. 

These five inspired routes all start with Chicago’s energy and unfold into memorable long‑weekend escapes. And each destination sits within an easy half‑day drive, offering history, nature, wine country, and small‑town charm just beyond our skyline.

A road trip for history buffs

Chicago: Explore the past, present, and future

Start on the South Side at the new Obama Presidential Center, rising high above Jackson Park as a modern landmark of civic history. 

Pair it with a visit to the nearby DuSable Black History Museum or head further south and spend a day exploring Pullman, a planned industrial community from the 1880s.

Next, head downtown for an architectural Chicago River boat tour, the most cinematic crash course in how this city rebuilt, reinvented, and reimagined itself over 150 years. After, make sure to stop by the Route 66 centennial start point at Navy Pier.

Road trip route: Route 66 through Illinois

Set your wheels on the Mother Road, where you’ll find some of the most iconic, nostalgia‑soaked miles of Route 66. This year marks the 100th anniversary of the legendary route, making it the perfect time for a history-infused road trip.

• Joliet greets road trippers with its Route 66 Welcome Center, the opulent Rialto Square Theatre, and a lineup of old‑school diners that channel pure roadside nostalgia.
• Wilmington is home to the towering Gemini Giant and a stretch of nostalgic Americana that feels lifted straight from Route 66’s mid‑century heyday.
• Pontiac invites travelers to explore the Route 66 Hall of Fame, wander its colorful mural walk, and step into the Livingston County War Museum for a dose of local history.
• Atlanta charms with its towering Paul Bunyan statue and the outdoor American Giants Museum that preserves the spirit of the Mother Road.
• Springfield brings Illinois history into vivid focus with the Lincoln Home, the Old State Capitol, and the Abraham Lincoln Presidential Library & Museum.

A great outdoors adventure

Chicago: See the city’s natural side

Chicago’s outdoors are as iconic as its architecture. Spend your first day along the Lakefront Trail — 18 miles of beaches, parks, and skyline views. Bike the shoreline to Promontory Point, or stretch out on the sand at North Avenue beach, or spot migratory birds at Montrose Beach.

Make time to wander Lincoln Park’s stunning grounds, which includes a historic zoo, lush ponds and boardwalks, and indoor gardens. Or head to the glass-enclosed Garfield Park Conservatory, one of the largest and most stunning botanical conservatories in the nation.

Road trip route: Canyons, cliffs, and outdoor thrills

Set out into Illinois, where sandstone canyons, forested trails, and river‑carved bluffs create some of the state’s most striking natural landscapes.

• On your way out of town, stop at the Morton Arboretum to wander the tree-filled landscape of this internationally renowned botanical garden .
• Starved Rock State Park delivers sandstone canyons, seasonal waterfalls, and sweeping overlooks that showcase some of Illinois’s most dramatic natural scenery. Join a kayak or canoe tour to see the stunning park from the water.
• Nearby, Matthiessen State Park offers forested trails, winding streams, and a peaceful atmosphere that feel worlds away from the city.
• If you’re up for a longer trip, make your way south to the Garden of the Gods, a jaw-dropping natural area home to dramatic rock formations, cliffs, and winding trails. Nearby, check out Shawnee Bluffs Canopy Tour for an exhilarating end to your road trip.

Frank Lloyd Wright around Chicago

Chicago: Frank Lloyd Wright’s city

Begin at Robie House in Hyde Park, a UNESCO World Heritage Site and one of Wright’s most celebrated Prairie School masterpieces. 

Stop by the downtown Rookery Building, where Wright designed the two-story atrium known fittingly as the Light Court. Head north to see the Emil Bach House in Rogers Park or south for the Roloson Houses, the world’s only Wright-designed row houses.

Before you hit the road, stop at the Chicago Architecture Center for models, exhibits, and context tracing Chicago’s evolution from Wright to the modernists.

Road trip route: Wright and beyond in the suburbs

Trace the evolution of American architecture beyond the city limits, where Prairie School masterpieces and modernist icons sit tucked into leafy neighborhoods and quiet river towns.

• Oak Park showcases Wright’s legacy through his Home & Studio, Unity Temple, and the world’s largest concentration of his early residential designs.
• Riverside is home to pristine examples of early Prairie School homes, including the Avery Coonley House and the Frederick F. Tomek house. The Riverside Historic District was designed by Olmsted and Vaux.
• Geneva adds mid‑century architectural gems tucked among historic storefronts and tree‑lined neighborhoods. The riverfront Fabyan Villa is a Prairie-style gem, accompanied by a Japanese garden and a Dutch windmill.
• Hampshire is where you’ll find the Muirhead Farmhouse, a unique example of Wright’s Usonian architecture that’s open to the public for tours.

Family‑friendly Chicago road trip

Chicago: An abundance of all-ages attractions

Spend the day at Navy Pier soaking in the splendor of the Chicago lakefront. Then hit the Chicago Museum Campus to explore the Shedd Aquarium, or the Field Museum — perennial kid favorites. 

Maggie Daley Park’s climbing walls and play garden are perfect for burning off energy, and a river cruise is a fun way to see the city without little legs getting tired.

Finally, spend some time exploring the hands-on Griffin Museum of Science and Industry, an interactive (and secretly educational) wonderland for all ages. Nearby, check out the new playground on the campus of the Obama Presidential Center. 

Road trip route: Kid‑friendly fun at every turn

Head out of the city to a string of easygoing Illinois towns where theme parks, hands‑on museums, and wide‑open nature make road‑tripping with kids feel effortless.

• Gurnee delivers big‑ticket family fun with the thrill rides of Six Flags Great America and the year‑round indoor waterpark at Great Wolf Lodge
• Union is home to the Illinois Railway Museum, where kids see vintage locomotives and even go for train rides
• Rockford blends learning and play with the Discovery Center Museum, the lush Nicholas Conservatory & Gardens, and the riverfront paths of Sinnissippi Park.
• Oregon invites families to explore Lowden State Park and take in the towering Black Hawk Statue overlooking the Rock River.
• DeKalb/Sycamore rounds out the route with pumpkin farms and seasonal festivals that celebrate small‑town charm.

The wine-lovers road trip

Chicago: Buzzy city wine bars

Begin in Logan Square, where you’ll find a trifecta of local wine bars: Webster’s Wine Bar, considered the city’s oldest wine bar; Easy Does It, with a spacious outdoor patio; and Outside Voices, focusing on natural and organic wines. 

For dinner, head to Bronzeville Winery, where the wine list features Black-owned labels and pioneering women winemakers. 

For a unique experience, join a winemaking class or tasting at Wild Blossom Meadery and Winery in the Beverly neighborhood.

Road trip route: Illinois wine country

Follow the rolling farmland and river valleys of northern Illinois, where family‑run wineries and sparkling‑wine specialists create a relaxed, scenic route perfect for an easy weekend escape.

• Roselle pours a sense of place at Lynfred Winery, Illinois’s oldest and largest family‑run winery.
• Peru offers méthode traditionnelle bubbles and relaxed tasting‑room vibes at August Hill Winery and Illinois Sparkling Co., and you can even take a guided tour of their wine cave for an atmospheric behind‑the‑scenes look at how their sparkling wines are crafted. 
• Travel south, stopping along the way at central Illinois wineries and vineyards like Mackinaw Valley Vineyard.
• Finish your pilgrimage with the Shawnee Hills Wine Trail, a scenic journey that includes 11 award-winning wineries interspersed throughout a lush national forest. 

In Chicago, Pride is more than just a month. The city celebrates LGBTQ+ culture all year long with film festivals, art exhibits, drag shows, theatrical events, and more. But June is truly a special time, when locals and visitors from around the world gather to celebrate the city’s vibrant LGBTQ+ history and community.

Here are just a few of the ways to celebrate Pride Month 2026 in Chicago, from our massive Pride Parade to welcoming neighborhood events.

Chicago Pride Festival and Parade

Chicago Pride Fest
Saturday, June 20 – Sunday, June 21
The 25th annual Chicago Pride Fest will take over the historic Northalsted community (the country’s first official LGBTQ+ neighborhood) with a jam-packed weekend of drag shows, dancing, local vendors, live music, and more.

Chicago Pride Parade
Sunday, June 28
This annual parade, a Chicago tradition for 55 years, is one of the largest Pride celebrations in the world. The joyful procession celebrates advocacy, equality, and LGBTQ+ history and culture as it marches through several lakefront neighborhoods.

Chicago neighborhood Pride festivals

Andersonville Midsommarfest
Friday, June 12 – Sunday, June 14
Back for its 60th year, Midsommarfest showcases the quirky neighborhood’s Swedish roots and inclusive community.

Back Lot Bash Chicago
Sturday, June 27 – Sunday, June 28
The block-party-style event, a staple for more than 20 years, includes a full weekend of music in Andersonville.

Pride South Side
Sunday, July 5
Keep the party going at Pride South Side, a colorful celebration of “Live in Action” at the DuSable Museum.

Museum nights and special events

Chicago White Sox Pride at the Park 
Wednesday, June 10
Watch the Chicago White Sox face off against the Braves and receive a Pride-themed hat with your ticket.

Pride Night at the Shedd
Saturday, June 13
Head to Chicago’s iconic Shedd Aquarium for an evening of high-energy DJs and an ocean-themed drag showcase.

Old Gold Summer ’26
Sunday, June 14
This daytime event features all-vinyl sets curated by the Good Girls DJs and friends (including legendary Chicago DJ Lori Branch) for an inter-generational celebration of queer joy. 

Pride Celebration at Wrigley Field
Monday, June 15
Enjoy local LGBTQ+-owned vendors, curated music and entertainment, fan activities, and more.

Pride Flotilla
Saturday, June 20
Get out on the water or watch from the beach as a parade of rainbow-covered boats float through Lake Michigan.

The Lesbian Social Club’s Pride Fest Takeover
Saturday, June 20
Join The Lesbian Social Club as they take over D.S. Tequila in Northalsted for 10 hours of non-stop partying, lesbian DJs, and Pride energy.

Ham-bingo at Hamburger Mary’s
Sunday, June 21
Have a gay old time at this drag bingo event, which supports the mission of local charity PrideArts Chicago.

Chicago Sky Pride Night
Wednesday, June 24
Cheer on the Chicago Sky as they take on the Portland Fire during this Pride Night showdown at Wintrust Arena.

Super Sapphic at smartbar
Friday, June 26
This massive celebration will take over the Metro with performances and DJ sets from lesbian and ally artists.

Navy Pier Pride
Saturday, June 27
Get queer at the Pier during this free, full-day event showcasing live music, dance, and more performances from LGBTQIA+ groups.

LGBTQ+ arts, theatre, and more

Art of Pride at Hyde Park Art Center
Sunday, June 7
Enjoy a free afternoon of queer joy and artistic expression, with performances and workshops led by LGBTQ+ artists, performers, and makers.

Don’t Say Be Gay
June 10 and 24
The Bughouse Theater presents this high-energy sketch comedy show about the joys of queer life.

Give It To Me Gay: A Queer Variety Show 
Thursdays through June 25
The Second City, Chicago’s legendary improv club, will celebrate queer joy with this special comedy show.

Queer as Folk Puppet Cabaret
Sunday, June 21
A unique showcase of puppetry and slam performances, hosted at the Color Club in Irving Park.

{THE} HOUR
Monday, June 29
This original show explore the lives of queer icons from different eras, hosted at The Den in Wicker Park.

Martin Wong: Chinatown USA
Now open through July 18
This exhibit at Wrightwood 659 features more than 100 paintings of visionary gay artist Martin Wong.

City in a Garden: Queer Art and Activism in Chicago
Now open through Aug. 16
Celebrate Pride Month at the Museum of Contemporary Art, with this exhibit highlighting Chicago’s role in queer art history.

Chicago’s local shopping streets tell the story of the city itself — creative, unique, and rooted in community. Across the city, these vibrant retail corridors offer a more personal way to shop while supporting the small businesses that help define each neighborhood.

Here are some top places to shop local in Chicago, one street at a time, with great food and sights along the way. And check out our map of Chicago’s top retail districts to start your shopping journey.

Andersonville: North Clark Street

Known as the “shop local Capital of Chicago,” the Andersonville neighborhood blends cool shops with the area’s lively bar and restaurant scene on this bustling street.

Find locally made apparel and products at Transit Tees — a space inspired by Chicago’s neighborhoods, transit lines, and city culture.

Right next door is Dearborn Denim, a family-owned business that offers jeans designed and sewn right in Chicago.

Keep walking down to Foursided, a one-of-a-kind art and frame store. The eclectic shop offers a “wonderland” feel with its wide selection of greeting cards, vintage objects, and curated gifts.

Take a  break at Eli Tea Bar, a modern tea café that specializes in loose leaf tea. From tea lattes to bubble tea, you’ll have a choice of 100 teas sourced from around the world. Keep browsing with a drink in hand at The Understudy, a hybrid theatre bookstore and coffee shop.

Lincoln Park: West Armitage Avenue

This serene, treelined street is filled with beautiful boutiques that sit under historic homes, making Armitage Avenue an inviting place to browse at your own pace.

Stop at Monica + Andy to see thoughtfully designed organic clothing and products for babies, children, and families. Make sure to check out their in-person events like baby and me yoga and educational workshops.

Nearby, Art Effect offers a fun selection of gifts and home décor, plus a room full of women’s clothing, jewelry, and accessories.

Next, head to Lost Soul Found, a modern apparel and home goods boutique that also features a coffee bar.

Refuel steps away at Klein’s Bakery & Café, a Venezuelan-inspired bakery with handcrafted cakes, artisanal coffee, and breakfast favorites. Tucked in an alley off the street is Beacon Doughnuts, where you can order a handmade doughnut with delicious flavors like cinnamon coffee cake and blackberry bismarck.

Streeterville: The Magnificent Mile

The Magnificent Mile is known worldwide as a must-visit shopping destination, with a mix of luxury brands, high-end malls, and locally rooted shops that deserve attention.

Find an impressive collection of everyday jewelry at Alexandra Marks, located inside The Shops at North Bridge.

With seven floors filled with shopping, the 900 North Michigan Shops brings together luxury retailers, boutiques, dining, and art installations. Also inside, Aster Hall is an elegant food hall with local favorites like Small Cheval.

Just a few blocks away, Pistachios Contemporary Art Jewelry carries handcrafted jewelry, including works by local artists. Round out your day at Mary Mary Gifts, a gift and home furnishing boutique in a gorgeous brownstone building.

Once you’re ready for food, walk over to Beatrix for options that range from sandwiches to in-house pastries. Cupitol also combines the best elements of a restaurant, bakery, café, and bar.

Logan Square: North Milwaukee Avenue

This artsy street draws in shoppers searching for unique finds in one of Chicago’s hippest neighborhoods.

At Fleur, a lifestyle boutique that started as a floral shop and grew into a destination for home goods, you’ll come across fine jewelry, fragrances, and more.

On the same block, Festive Collective brings color to the street with party goods, stationery, vintage finds, and home items.

Walk across the square to Wolfbait & B-girls, which operates as a handmade marketplace showcasing work from more than 300 Chicago-based artists and designers.

Stop by Chiqueolatte to order from an inventive drink menu and pastries from neighborhood bakeries. Another nearby favorite, Pedestrian Coffee, provides high-quality coffee that’s sourced globally and roasted locally.

Explore more: Keep heading north on Milwaukee Avenue and you’ll hit the Avondale neighborhood, where you’ll find quirky shops and lots of thrift finds.

Pilsen: West 18th Street

Reflecting the neighborhood’s strong Hispanic culture, 18th Street in the Pilsen neighborhood comes alive with dynamic storefronts and community-driven spaces.

Browse gifts and apparel from Mexico, Latin America, and local artists at the colorful Mestiza Shop.

Walk around the corner to Semillas, a hybrid plant shop, floral studio, and community space. Sign up for their hands-on workshops that guide you through the art of floral design, plant care, and more.

For a sweet treat, Chocolat Uzma specializes in small-batch, handcrafted chocolates inspired by South Asian flavors. Café Jumping Bean, a favorite amongst residents, brings excellent coffee and snacks.

Chinatown: South Wentworth Ave

At the center of Chicago’s century-old Chinatown, Wentworth Avenue is home to an array of locally owned businesses in this historic neighborhood.

Have your pick at a wide selection of imported Asian treats when you stop at Ichiban Candy and Snacks.

If you’re looking for your next gift, The Midi Chicago sells cute toys, blind boxe, gifts, and lifestyle finds with new product drops every week.

Complete your visit at Vital Chinatown, a cultural epicenter rooted in streetwear, fashion, and community programming. From private screenings to footwork competitions, drop by an upcoming event soon.

Walk down the street to Chiu Quon Bakery, the oldest Chinese bakery in Chicago. Try customer favorites including their BBQ pork baos, Portuguese egg tarts, and baby moon cakes. Stop at Hello Jasmine for authentic Taiwanese bento boxes, snacks, and drinks.

Hyde Park: West 53rd Street

Situated in the city’s well-known cultural hub, Hyde Park’s 53rd Street anchors the neighborhood’s charming shopping scene.

Wander to Suuri Design, a mother-and-daughter lifestyle brand specializing in unique handcrafted jewelry and artisan home and body care products.

A short walk away, The Silver Room stands as a Chicago institution curating jewelry, clothing, music, and more while functioning as a gathering place for art, culture, and community.

Walk a few blocks to Call & Response Books, a Black woman-owned neighborhood bookstore with a wide-ranging selection.

Visit Sip & Savor for a coffee and satisfying snack — the lifestyle brand serves up bold brews, apparel, and gifts. Down the street is Café 53, highly regarded for their oven-fresh and vegan sandwiches.

Lincoln Square: North Lincoln Avenue

Serving as the heart of the neighborhood’s shopping scene, the cobblestone stretch of Lincoln Avenue offers family-friendly stores alongside quaint cafes and gathering places.

At Timeless Toys, you can shop a curated selection of educational and imaginative toys, games, and books with every item picked by its team of certified play experts.

Across the street, Midwest Nice celebrates the region’s warm welcomes through apparel, gifts, and artwork from more than 100 Midwest-based makers.

The iconic landmark known as Merz Apothecary specializes in unique and natural health, personal care, and beauty products sourced from around the world.

If you’re feeling hungry, grab a bite to eat at Gene’s Sausage Shop and Delicatessen — a sprawling two-story European market offering fresh products, homemade sausages, and imported foods. Continue down the block to Giddings Plaza and recharge on a bench or near the fountain. This intimate gathering place also hosts the fabulous outdoor Willow Café & Bistro, a cozy coffeehouse and bakery.

Little Village: West 26th Street

Known for its proud Mexican heritage the Little Village neighborhood centers on 26th Street (considered the city’s “second Magnificent Mile”), where a lively mix of shops showcases the community’s deep cultural roots.

Browse traditional crafts including textiles, jewelry, and ceramics made by Mexican artists based locally and in Mexico at Artesanías Elena.

Dulcelandia, known for their signature candy-filled walls and colorful candy towers, is a well-known destination for Mexican candy and party items.

Finally, OK Corral Western Wear carries western clothing, boots, hats, and accessories for men, women, and children.

Enjoy a comforting breakfast and brunch at La Catedral Café, an award-winning Mexican café serving up a Guadalajara-inspired extensive menu. Kafecito offers a cozy atmosphere with tortas, paninis, fresh juices, and coffees.

Explore more: Discover more local shopping at these unique neighborhoods for boutique shopping.

This summer marks the inaugural Windy City Boat & Yacht Show, a brand new in-water boat show taking place at Burnham Harbor.

This exciting event will take over the Chicago lakefront this summer from Friday, June 12 to Sunday, June 14. The public is welcome to hop aboard and explore everything from sleek speedboats to luxurious yachts.

The Chicagoland area has long been one of the country’s most active boating destinations, and this new show will bring a world-class in-water experience to the heart of downtown for the first time.

Whether you’re a seasoned boater, a curious first-timer, or just looking for a spectacular day on Chicago’s lakefront, there’s plenty you’ll need to know before you go. Here’s a complete guide to the inaugural edition of the Windy City Boat & Yacht Show in Chicago.

What is the Windy City Boat & Yacht Show?

Chicago’s exciting new summer event, the Windy City Boat & Yacht Show, is a celebration of the Great Lakes boating lifestyle. 

Held at downtown Burnham Harbor, the inaugural show will feature more than 100 vessels that showcase the latest in luxury yachts, powerboats, sailing vessels, and more — all with a stunning waterfront and skyline backdrop. 

Unlike a traditional indoor expo, this show is designed to feel like spending a summer day out on the waves. You’ll step aboard boats, walk the docks, take test drives, and be among the first to see new boat models, marine tech, and accessories. 

Explore more: Soak in Chicago’s world-class waterfront with a stroll through the nearby Museum Campus, just a short distance from Burnham Harbor.

When is the Windy City Boat & Yacht Show?

The Windy City Boat & Yacht Show runs from Friday, June 12 through Sunday, June 14, 2026.

Here are the show hours:

• Friday, June 12: 10 a.m. to 7 p.m.
• Saturday, June 13: 10 a.m. to 7 p.m.
• Sunday, June 14: 10 a.m. to 5 p.m.

Where is the Windy City Boat & Yacht Show?

The Windy City Boat & Yacht Show takes place at Burnham Harbor, located at 1559 S. Lake Shore Drive in Chicago. Nestled near Soldier Field and the Museum Campus, Burnham Harbor is an easy-to-access waterfront destination — just steps from Grant Park and minutes from the Loop.

What can I do at the Windy City Boat & Yacht Show?

This fully immersive waterfront experience has something for every kind of visitor.

On the water, you’ll find more than 100 boats — including new 2026 model debuts and premium brokerage listings — ranging from nimble powerboats and classic sailboats to full-size cruising yachts up to 75 feet. Many vessels are open for boarding, so you can explore interiors and admire the view from the deck. Select boats are available for test drives, giving you a genuine taste of Chicago’s lake life.

Back on land, browse over 50 exhibits featuring the latest in marine technology, safety gear, luxury accessories, kayaks, stand-up paddleboards, and all the boating essentials. Grab a bite at on-site vendors, enjoy family-friendly entertainment, and soak up the energy of the waterfront atmosphere.

Special programming throughout the weekend includes:

• On-Water Sailing Sessions: These beginner sailing classes get you out on the water for hands-on instruction, no experience required
• Cruisers Classroom: Elevate your boating knowledge with expert-led discussions and panels covering everything from navigation to seamanship, available all three days
• Yacht Club Lounge: This elevated social space is inspired by Chicago’s prestigious yacht club tradition, featuring live music, food, and handcrafted cocktails

How much does it cost to go to the Windy City Boat & Yacht Show?

Tickets for the Windy City Boat & Yacht Show are $20 for a one-day general admission pass (valid any single day) or $35 for a two-day pass. Children ages 11 and under are free.

All tickets must be purchased online. There will be no on-site ticket sales. The show is held rain or shine.

Active military and veterans are eligible for a complimentary one-day general admission ticket. Request yours in advance.

Is the Windy City Boat & Yacht Show open to the public?

Yes! The show is open to all ages and all levels of boating experience.

Families are welcome, though strollers are not permitted on the show grounds for safety reasons. A designated stroller parking area is available near the main entrance.

A few things to keep in mind: pets are not permitted (except service animals), and you should wear comfortable shoes that are easy to slip on and off, since boarding vessels may require it. Sunscreen and a hat are strongly recommended for the outdoor venue.

How do I get to the Windy City Boat & Yacht Show?

Burnham Harbor is conveniently accessible via several types of transportation.

• CTA ‘L’ trains: Take the Red, Orange, or Green Line to the Roosevelt station and walk east to the harbor.
• Bikes: Grab your bike or a Divvy rental and cruise down the scenic Lakefront Trail. Bike racks will be available within the show grounds.
• Water Taxi: Accessible directly to the show site from nearby downtown locations.
• Driving: Parking is available at Soldier Field South Lot, Waldron Parking Garage, and other parking garages. See full parking details.

Learn more about getting to the show.

What is there to do near the Windy City Boat & Yacht Show?

The city’s bustling South Loop neighborhood is filled with things to do and see before and after the show.

• Museum Campus, home to three top museums and jaw-dropping skyline views
• The Lakefront Trail, a waterfront pedestrian path for biking and walking 
• Chinatown, a historic cultural destination filled with dining and shopping
• Prairie Avenue historic district, with landmarks like Glessner House and the Chicago Women’s Park & Garden 

Nearby restaurants include:

• Fatpour Tap Works, a casual brewpub known for its generous pours and bar-food menu
• Il Culaccino, an upscale casual restaurant that offers traditional Italian cuisine and a scenic patio
• The Chicago Firehouse Restaurant, a classic steakhouse in a 1905 firehouse 
• Weather Mark Tavern, a casual nautical-themed space with burgers, pints, and more
• The Staley, an upscale sports bar founded by former Chicago Bear Israel Idonije
• Haidilao, serving Szechuan-style hot pot directly from China
• Mustard Seed Kitchen, the perfect place to grab a hearty bite to eat on the go
• Williams Inn, a family-owned spot serving pan pizza, Italian beef, and other casual bar food
• Moody Tongue Brewing Company, a Michelin-starred brewery with fine-dining and bar spaces 

Explore more dining options near Burnham Harbor. 

Before leaving Chicago, make O’Hare (ORD) or Midway (MDW) International Airports your last shopping stop. Both airports showcase local foods, favorite brands, and uniquely Chicago gifts that let travelers take home a piece of the city. From gourmet treats and sports gear to locally inspired apparel and museum-quality keepsakes, these shops make it easy to find meaningful souvenirs after your sightseeing adventures end.

O’Hare International Airport

BLVD & Branch brings elevated Chicago style to O’Hare with a curated selection of locally inspired gifts, apparel, and accessories. Located in Terminal 5, near Gate M30, the boutique spotlights products from Chicago makers and brands, prioritizing items from local, minority-, and women-owned businesses. Shoppers will find gourmet treats, gifts for the home, jewelry, and Chicago sports-themed merchandise.

For a souvenir that literally says Chicago, ChiBoys delivers fashion-forward items at Terminal 3, near Gate H6. The retailer’s Windy City-themed streetwear highlights Chicago’s culture, architecture, and historic neighborhoods. Items featuring original ChiBoys designs include T-shirts, hoodies, beanies, trucker and bucket hats, joggers, headphones, and more. You can even find a baby onesie or a hoodie for your dog.

The I Love Chicago boutique is packed with high-end, city-themed merchandise and easy-to-pack souvenirs in Terminal 5, near Gate M11. Travelers can browse T-shirts, magnets, mugs, hats, and novelty gifts featuring Chicago’s skyline, sports teams, and famous landmarks. Local artists make some of the store’s products, including clothing, accessories, apothecary items, and locally made home accessories.

Take home a piece of a world-class Chicago museum at the Field Museum Store in Terminal 1, near Gate B8. Inspired by the beloved Field Museum, the shop features educational toys, books, science-themed gifts, and unique merchandise tied to natural history and discovery. Visitors can find everything from dinosaur memorabilia to sophisticated keepsakes. It’s a thoughtful alternative to traditional souvenirs and a great reminder of Chicago’s cultural attractions.

Midway International Airport

Few gifts feel more classically Chicago than a box of Fannie May chocolates. Near Gate A5 at Midway, travelers can visit the Fannie May store to stock up on the confectioner’s signature treats, which include Pixies, Mint Meltaways, and creamy caramels. The shop offers a box of nostalgia with its beautifully packaged sweets that travel well and make great gifts. Founded in 1920 in downtown Chicago, Fannie May has grown from its original shop on North LaSalle Street to a gourmet chocolatier with stores across the Midwest.

Sports fans can celebrate Chicago’s legendary teams with a stop at Chicago Sports in Concourse B, near Gate B10. The store is filled with apparel, hats, collectibles, signs, and accessories representing hometown favorites like the Cubs, White Sox, Bulls, Bears, and Blackhawks. Whether you’re a lifelong fan or simply want a souvenir tied to the city’s passionate sports culture, the shop offers plenty of spirited team gear options.

With a convenient location near Gate A5’s shopping and dining area, The Atrium is a one-stop shop. Pick up gifts and travel essentials like cosmetics, headphones, socks, sunglasses, and more before boarding your flight. Shoppers can browse merchandise that reflects Chicago while enjoying the lively atmosphere of the airport’s main concourse. It’s your place to squeeze in one final taste of Chicago before takeoff, with self-checkout making purchases quick and easy.

Discover more things to do at Chicago’s international airports.

This month in Chicago, attend the world’s largest free blues festival, admire iconic works in one of the world’s top art museums, and stroll an open-air art fair — all without spending a dime.

Chicago is bursting with free things to do this month, including plenty of free museum days, neighborhood festivals, live music, outdoor markets, dance performances, fireworks shows, and more.

Start planning your budget trip to Chicago with this round-up of the free things to do and see throughout June 2026.

1. Visit the new Obama Presidential Center

June 20 – 21, 2026
It’s a historic moment for the city of Chicago and the nation — the Obama Presidential Center is officially opening its doors to the public on Juneteenth weekend in the city’s historic Hyde Park neighborhood.

The campus will host a free open-house-style weekend on Saturday, June 20 and Sunday, June 21.

The public is welcome to come enjoy performances, family activities, food, art, and storytelling across the lakefront grounds.

Can’t make it for opening weekend? The Obama Presidential Center will offer free admission for Illinois residents every Tuesday year-round.

2. Party at the Chicago Pride Parade

June 28, 2026
June is Pride Month and there are plenty of fun (and free!) ways to celebrate all around Chicago.

The city’s signature Pride celebrations culminate with the annual Chicago Pride Parade, which takes over the streets of Northalsted, the oldest official gay neighborhood in the country. The parade is back for its 55th year on Sunday, June 28.

While you’re in the neighborhood, check out the Legacy Walk. This free outdoor museum honors the historic contributions of the LGBTQ+ community.

Plus, check out more free ways to celebrate Pride Month in Chicago:

• Art of Pride at Hyde Park Art Center (June 7) is an intergenerational afternoon celebrating queer joy
• Navy Pier Pride (June 27) brings a free family-friendly  Pride celebration to the Chicago lakefront
• Pride South Side (July 5) features local vendors, musicians, drag performers, and more in Washington Park

3. Attend the Chicago Blues Festival

June 4 – 7, 2026
Chicago redefined the blues for the world. And every summer, the city honors that legacy with the world’s largest free blues festival.

A summertime staple since 1984, the Chicago Blues Festival draws hundreds of thousands of fans and blues icons from all over the country.

Highlights from this year’s line-up include Taj Mahal, Charlie Musselwhite, Elvin Bishop, a tribute to Billy Branch, Ronnie Baker Brooks, Willie Clayton, a celebration of women in blues, and more.

The best part — all performances throughout the four-day festival are completely free and open to the public. Catch blues performances throughout Millennium Park and neighborhood venues like the Ramova Theatre and Maxwell Street Market.

4. Enjoy a free museum day

Throughout June
Spend an afternoon wandering through a Chicago museum, where you can dive into fascinating history, provocative contemporary art, and galaxies far, far away.

Here are the upcoming free museum days in Chicago this month for Illinois residents:

• Field Museum is free every Wednesday
• Griffin Museum of Science and Industry is free on June 4 and 19
• Art Institute of Chicago is free every Thursday evening after 5 p.m.
• Shedd Aquarium is free every Tuesday evening after 5 p.m.
• Adler Planetarium is free on June 3, 10, 17, and 24
• Peggy Notebaert Nature Museum is free on June 1 – 3 and 22 – 24

You can also visit one of the city’s always-free museums, like the National Museum of Puerto Rican Arts and Culture, the National Museum of Mexican Art, and more.

Explore more: Mark your calendar for free museum days throughout the year.

5. Hear live music in Millennium Park

Throughout June
The city’s iconic Millennium Park is filled with live music every summer, from major music festivals to casual weekday concerts.

Check out the packed lineup of free shows coming to the Pritzker Pavilion this June. No tickets needed, just show up and grab a spot on the Great Lawn to enjoy live music under the stars.

Millennium Park Music Series, beginning June 15, is a free outdoor concert series featuring top local and touring acts, all with a skyline backdrop in Millennium Park.

• Monday, June 15: Arrested Development, Linda Sol, DJ Ca$h Era
• Thursday, June 18: Let the Spirit Out! A Jubilant Celebration of Juneteenth
• Monday, June 22: Sheila E., Melody Angel, DJ Larz Natural
• Thursday, June 25: Patrice Rushen, Sparklmami, DJ Shon Dervis
• Monday, June 29: Sir Chloe, Venus & the Flytraps, DJ Jill Hopkins

Grant Park Music Festival, beginning June 10, is a 90-year tradition that bring free classical music to Millennium Park all summer long.

• Wednesday, June 10: Bernstein West Side Story
• Friday, June 12 and Saturday, June 13: Brahms Symphony No. 4
• Wednesday, June 17: Haydn Military Symphony
• Friday, June 19 and Saturday, June 20: Copland Symphony No. 3
• Wednesday, June 24: Barber Violin Concerto

Check out the full Millennium Park events calendar for more free summer events, like free weekend workout classes.

6. Kick off street festival season

Almost every Chicago neighborhood has its own summer street festival, including parades, music festivals, block parties, art fairs, and more dedicated to food, culture, and beyond.

Here are just a few of the neighborhood festivals and events with free admission this June:

• 57th Street Art Fair (June 6 – 7): This long-running event features an array of artists from all over the country in the historic Hyde Park neighborhood.
• Puerto Rican Day People’s Parade (June 13): Immerse yourself in Puerto Rican culture and a celebratory atmosphere during this lively parade in Humboldt Park.
• Bronzeville Art Trolley Tour (June 19): Enjoy free double-decker bus rides that take art lovers to a variety of Bronzeville galleries.
• Millennium Art Festival (June 27 and 28): Browse more than 100 artists just steps from Millennium Park at this free art fair.
• Fiesta Back of the Yards (June 19 – 21): Enjoy a mix of live entertainment, Latin cuisine, carnival rides, and dance performances.

Explore more: Check out the full schedule of neighborhood street festivals in Chicago all summer long.

7. Shop the Maxwell Street Market

Sunday, June 7, 2026
Come experience a true piece of Chicago history. The open-air Maxwell Street Market has been a local tradition for more than a century.

This vibrant outdoor market is back for the season, featuring an eclectic mix of food, handmade crafts, housewares, clothing, live music, and more.

The June market will include special pop-up performances from the Chicago Blues Festival, including:

• DJ James Porter
• Studebaker John’s Maxwell Street Kings
• John Primer & Steve Bell
• Harmonica Hinds Duo

Explore more: Check out Chicago neighborhood farmers markets in every corner of the city.

8. Experience Chicago’s dance scene

Chicago’s diverse and dynamic dance legacy spans everything from classic ballet to stepping and other modern forms. And June is the perfect time to experience it for yourself.

The 13th annual Chicago Dance Month will offer free events all month long, starting with a kick-off performance at Navy Pier on Saturday, May 30.

Here’s a preview of some upcoming Chicago Dance Month events:

• Pier Dance (Wednesdays, June 3 – 24): Enjoy free dance lessons from a variety of genres at Navy Pier each week.
• Wave Wall Moves (Saturdays, June 6 – 27): Check out free performances along the lakefront from the city’s diverse dance community.
• NeighborhoodMOVES (June 8 – 27): This neighborhood event series will include community workshops, improvisation jams, panel discussions, dance film screenings, and more.

9. Watch the summer fireworks on the lakefront

Throughout June
The Navy Pier summer fireworks display is one of the most iconic parts of a Chicago summer. These free shows take place on Wednesdays at 9 p.m. and Saturdays at 10 p.m. all summer long.

June fireworks shows at Navy Pier include:

• Wednesday, June 3
• Saturday, June 6
• Wednesday, June 10
• Saturday, June 13
• Wednesday, June 17
• Saturday, June 20
• Wednesday, June 24
• Saturday, June 27

The breathtaking display is accompanied by a soundtrack of popular music, with special themed nights for holidays. The best places to watch the show include on the east and south sides of the Pier or along the nearby lakefront.

10. Hear live jazz at a museum

The Museum of Contemporary Art’s popular Tuesdays on the Terrace series is back, kicking off its 27th year on Tuesday, June 16.

The beloved series brings free weekly concerts to the museum’s lawn, putting a spotlight in the city’s internatioanlly renowned music scene. This month, mark your calendar for the following local acts:

• June 16: Kahil El’Zabar with The Ethnic Heritage Ensemble
• June 23: Alejandro Salazar
• June 30: Will Miller

Guests are encouraged to bring their own picnics; light refreshments and a full bar with cold beverages, wine, and cocktails are available for sale. Make sure to save time to explore the museum’s latest exhibits — the museum is open late on Tuesdays and free for Illinois residents.

There’s so much to celebrate this June — especially the start of summer in Chicago, which brings a jam-packed schedule of block parties, festivals, concerts, art exhibits, parades, tasting events, outdoor adventures, and more.

Check out these top picks for things to do in Chicago throughout June 2026.

Top events in Chicago this June

Chicago Blues Festival (June 4 – 7, 2026): Enjoy world-class blues at one of Chicago’s most legendary music festivals, drawing hundreds of thousands of fans from all over the country to Millennium Park.

U.S. Men’s National Team vs. Germany (June 6): Don’t miss the official send-off match for the U.S. Men’s National Team as they face off against Germany before their turn on the world stage.

57th Street Art Fair (June 6 – 7, 2026): Hyde Park will be filled with art for the 79th annual 57th Street Art Festival, showcasing local artists and their work, live music, food, family-friendly activities, and more.

Puerto Rican Festival and People’s Parade (June 11 – 14, 2026): Head to Humboldt Park for a massive festival of Puerto Rican culture, with games, live music, carnival rides, and plenty of local food and drinks.

Andersonville Midsommarfest (June 12 – 14, 2026): For more than 50 years, this summer festival has celebrated Andersonville’s Swedish heritage and LGBTQ+ Pride with live music, kids’ activities, food, drinks, and more.

Windy City Boat & Yacht Show (June 12 – 14): Sail into summer at this in-water boat and yacht show at Burnham Harbor. Check out the latest boat vessels, gear, and accessories while soaking up the waterfront and skyline views to boot.

James Beard Awards (June 12 – 16): These prestigious awards are hosted in Chicago each year, cementing the city’s status as a culinary powerhouse. Check out fun crossovers and dinners leading up to the main event on June 15 at the Lyric Opera.

Millennium Park Summer Music Series (starting June 15): This free outdoor concert series features top local and touring acts, all with a skyline backdrop in Millennium Park.

Millennium Park Summer Film Series (starting June 30): Enjoy free movies under the stars during this beloved Chicago summer tradition. This June, catch a 30th anniversary screening of Independence Day.

Obama Presidential Center opening weekend (June 19 – 21): Juneteenth marks the highly anticipated grand opening of the Obama Presidential Center, which is offering a free community open-house to celebrate.

Chicago Pride Fest (June 20 – 21): Celebrate Pride Month with multiple stages with live music, more than 150 food and merchandise vendors, drag shows, dance performances, and more.

Chicago Pride Parade (June 28, 2026): One of the largest Pride celebrations in the world, the Chicago Pride Parade marches through the vibrant Northalsted neighborhood on the last Sunday of June.

More events in Chicago this June

Physical Theater Festival (June 1 – 7): This year is the 13th annual festival, which showcases seven days of live theater from across different countries including Argentina, Brazil, Colombia, Iceland, Scotland, and the U.K.

Chicago Dance Month (through June): This month-long, citywide celebration brings dance performances across genres to venues throughout the city.

Millennium Park Summer Workouts (through June): Start your Saturday mornings off right with free outdoor fitness classes in the heart of the city, from yoga to zumba to pilates and beyond.

Grant Park Music Festival (starting June 10): A Chicago summer tradition for more than 90 years, the free Grant Park Music Festival delivers world-class classical performances in the scenic Pritzker Pavilion.

Ribfest Chicago (June 5 – 7): Dig into mouthwatering meats at Ribfest Chicago, a family-friendly street festival in North Center with two stages, local beers, whiskey, and bourbon tastings.

Lincoln Park Greek Fest (June 5 – 7): From traditional Greek food to a live Greek orchestra, the Lincoln Park Greek Festival honors Hellenic culture with a weekend full of fun.

Beyond Wonderland (June 6 – 7): Experience this fantastical music festival on Chicago’s lakefront, with two days dedicated to electronic music.

Art of Pride (June 7): This family-friendly event at the Hyde Park Art Center celebrates LGBTQ+ artists, performers, and makers with different art activities, live music, a vendor market, and more.

Pokémon GO Fest (June 5 – 7): Chicago will be home to one of the most anticipated events in the Pokémon GO calendar, with rare Pokémon spawns and citywide gameplay.

INSIDE DESIGN (June 6 – 7): NeoCon attendees can take advantage of exclusive design-driven events, created in collaboration with the Design Museum of Chicago.

Maxwell Street Market (June 7): Browse Chicago’s century-old Maxwell Street Market on select Sundays this summer for unique crafts, live music, and delicious global street food.

Fulton Market Design Days (June 8 – 10): The fourth annual Design Days brings together leading brands, immersive pop-ups, and more in a neighborhood-wide celebration in Chicago’s vibrant Fulton Market district.

Kayak for Conservation (through June): These unique eco-kayak tours led by the Shedd Aquarium focus on the natural environment of the Chicago River and the wildlife that call it home.

Chicago Fire Soccer Celebration at Recess (June 11 – July 19): Catch every minute of the soccer action during this month-long watch party, featuring live screenings of every match.

Lyrical Lemonade Summer Smash (June 12 – 14): Skrillex and Playboi Carti are headlining this summertime music festival at SeatGeek Stadium in Bridgeview.

Chicago Greeter Pop-Up Tours (June 13 and 27): What better way to explore Chicago like a local than with free neighborhood tours led by actual locals? This month, catch free pop-up tours through Pilsen and Hyde Park.

Old Town Art Fair (June 13 – 14): A long-standing staple of Chicago’s festival scene, this outdoor market showcases more than 200 visual artists from around the country.

Wells Street Art Festival (June 13 – 14): Head to Wells Street in Old Town for this annual summer art fest that draws artists from all over the world for a weekend of art, food, and fun.

Bronzeville Art Trolley Tour (June 19): Art lovers won’t want to miss the opportunity to visit multiple galleries throughout the Bronzeville Art District during these free trolley tours.

Dragon Boat Race for Literacy (June 20): Watch Chinese Dragon Boats race down the Chicago River during this family-friendly day in the Chinatown neighborhood.

Fiesta Back of the Yards (June 19 – 21): Celebrate community pride at Fiesta Back of the Yards, with a mix of live entertainment, Latin cuisine, carnival rides, and dance performances.

Taste of Randolph (June 19 – 21, 2026): Indulge in gourmet bites and live music at Taste of Randolph, celebrating the best of the West Loop’s buzzing restaurant scene.

Cinema/Chicago Summer Screenings (through June): This annual summer series from the Chicago International Film Festival brings free screenings spotlighting international cinema.

Bronzeville Art District Trolley Tour (June 19): Tour multiple galleries throughout the Bronzeville neighborhood with a free trolley every third Friday of the month.

Chicago Food Truck Festival (June 20 – 21): The South Loop will be hosting its annual food truck festival featuring the city’s best mobile chefs.

Gold Coast Art Fair (June 20 – 21): The 68th annual edition of this downtown art fair will let guests browse handmade goods and art from over 200 artists, offering a mix of painting, ceramics, jewelry, and much more.

Malt Row on Damen Beer Stroll (June 24): Sip samples from local breweries, distilleries, and wineries, while browsing local shops and businesses along Ravenswood’s popular Malt Row.

Flavors of Albany Park (June 24): Sample international cuisine from over 50 restaurants during this annual event highlighting the neighborhood’s culinary diversity.

Zoo Fiesta (June 26): Lincoln Park Zoo comes alive with Latine culture at Zoo Fiesta, a festive after-hours event featuring live music, authentic food and drink, cultural performances, and much more.

Logan Square Arts Festival (June 26 – 28): This dynamic neighborhood festival highlights a variety of artists, neighborhood restaurants, locally crafted beer and cocktails, and a diverse lineup of performances.

Porchfest Roscoe Village (June 28): This unique music festival showcases local artists by turning neighborhood porches into intimate outdoor stages.

Chicago Taco & Tequila Fest (June 26 – 27): This two-day fiesta features live music, tacos from favorite Chicago restaurants, plus a tequila tasting and margarita flight.

Millennium Art Festival (June 27 – 28): This juried art showcase brings more than 100 artists, plus live music and food, to Chicago’s famed Michigan Avenue.

Jazzin’ at the Shedd (through June): Bring some fun to your weeknights with this summer series at the Shedd Aquarium, featuring top jazz ensembles, cocktails, and unbeatable skyline views every Wednesday.

Tuesdays on the Terrace (through June): The Museum of Contemporary Art’s summer concert series kicks off in June, with free live music on the lawn every Tuesday evening.

Fireworks at Navy Pier (through June): Head to the lakefront to catch this dazzling fireworks show, held every Wednesday and Saturday this summer.

Movies at Gallagher Way (through June): Enjoy free movie nights in the shadow of Wrigley Field, complete with food and drink vendors, and plenty of outdoor family fun. In June, don’t miss films like Zootopia 2 and Cool Runnings.

Art on the Mart (through June): This evening art and light installation is back with fresh works, lighting up the Chicago River each night.

Chicago Humanities Festival (through June): The spring celebration brings iconic names to Chicago for various nights of conversation, including author actor Billy Eichner, authors Matt Haig and Ann Patchett, and Dr. Jill Biden,

Chicago Farmers Markets (through June): Shop locally grown produce, artisanal goods, ready-to-eat foods, and more at seasonal neighborhood farmers markets throughout the city.

Green City Market (through June): The Lincoln Park Green City Market takes place every Wednesday and Saturday in June, bringing together dozens of vendors from local and Midwest farms, restaurants, bakeries, and more.

Theater of the Mind (through June): Co-created by artist David Byrne and Mala Gaonkar, this new immersive, multi-sensory experience invites audiences to explore the inner workings of the mind through sound, storytelling and interactive environments.

Anne Frank: The Exhibition (through June): Step inside a meticulous full-scale reconstruction of the Annex where Anne Frank and her family hid, now at the Museum of Science and Industry.

Dancing the Revolution (through June): This new exhibit at the Museum of Contemporary Art Chicago explores the genres of reggaeton and dancehall as tools of protest and revolution.

Martin Wong: Chinatown USA (through June): The newest exhibit at Wrightwood 659 puts the spotlight on artist Martin Wong and his vivid depictions of New York’s Chinatown, highlighting themes of community and identity.