In 1871, the Great Chicago Fire swept through the city and destroyed much of downtown. Yet Chicago rose from the ashes, building back bigger and better and driving the creation of the world’s first-ever skyscrapers.

Today, the city’s Major League Soccer team pays homage to that resilience and unbeatable spirit. The Chicago Fire Football Club are an undeniable force in the league, filling historic Soldier Field with an energy like no other.

We asked Chicago Fire FC players from Chicago and around the world about their favorite things to go around the city. Whether you’re in town to soak up all the soccer action or just want to enjoy quintessential summer in Chicago, this guide is a great starting point to start exploring great bites and top attractions.

What is your favorite restaurant in Chicago?

“We’ve been to Tre Dita, Maple & Ash, Gus’ Sip and Dip and Aba, those are always good. Still trying to find some more.” — Chris Brady, goalkeeper, Naperville, Illinois

“I think wings are probably what I enjoy the most on an off day. I like everywhere to be honest, but there’s a place called The Whistle. That one’s pretty good. I think Portillo’s is probably the spot I go to the most, but I also like El Solazo.” — Sergio Oregel Jr., midfielder, Chicago, Illinois

“I like this place on the North Side. It’s called Taconazo. It’s a Mexican place on the street.” — Mauricio Pineda, midfielder, Bolingbrook, Illinois

“Qing Xiang Yuan dumplings Chinatown, Alla Vita, and Gibson’s Italia are my top three.” — Sam Rogers, defender, Seattle, Washington

“Violi and Zaza’s Italian. Love Zaza’s.” — Andrew Gutman, defender, Hinsdale, Illinois

“I went to this restaurant Lyra, the Greek one. I liked it. That’s for sure one of the things that I enjoyed.” — Anton Salétros, midfielder, Stockholm, Sweden

“Armitage Ale House. I think that’s the best restaurant in the city. They have a very good burger.” — Christopher Cupps, defender, Chicago, Illinois

“I would say my favorite restaurant in Chicago would be Trivoli Tavern.” — Jason Shokalook, forward, Erie, Pennsylvania 

“Our new favourite restaurant is Sushi-san. Amazing food and vibes.” — Joel Waterman, defender, Langley, British Columbia 

“Two of my favorite restaurants are Creepies and Elske in West Loop. I also really like Obélix, a French bistro in River North and El Che, an Argentinian steak house. Apart from that, Matilda and La Lunita are some great modern Mexican restaurants. Rose Mary is a super cool Croatian-Italian restaurant. Tre Dita and Gibsons Italia are two great Italian spots. For coffee, I really like Metric Coffee, especially their shop Milli by Metric. Candor in Wicker Park is a great little spot too.” — Philip Zinckernagel, forward, Copenhagen, Denmark 

What is your favorite thing to do in Chicago?

“I’ve been big into scootering around the city. Also, going to all the museums in South Loop area. That’s kind of dope.” — Chris Brady, goalkeeper, Naperville, Illinois

“Watching the Bulls, I have season ticket[s]. I go every night that they play at the United Center.” — Andre Franco, midfielder, Lisbon, Portugal

“I like any boat rides on the river or the lake. Something I’d like to do is kayak on the river – have always wanted to.” — Mauricio Pineda, midfielder, Bolingbrook, Illinois

“The Chicago Architecture Boat Tour is sick.” — Christopher Cupps, defender, Chicago, Illinois

“One thing that I liked to enjoy this past summer is just going down to the lake with the family, and swim there. I thought those were really good times.” — Jeff Gal, goalkeeper, Bartlett, Illinois

“I like visiting museums. I like going to NBA games or visiting downtown Chicago — the river or the lake with the boats. There’s many things to do.” — Maren Haile-Selassie, midfielder, Zurich, Switzerland

“Probably the riverboat cruise, because the architecture was really cool. When the weather’s nice, I like hiking, especially with our dogs.” — Jonathan Dean, defender, Macon, Georgia

Learn more about the Chicago Fire and how you can take part in all the match day excitement.

Summer in Chicago just wouldn’t feel complete without the city’s beloved street festivals.

Scattered throughout lively neighborhoods, these community gatherings are the perfect excuse to soak up sunshine, enjoy that classic block-party energy, and dive into food, art, and culture that define Chicago’s character.

Most festivals suggest a small donation at the entrance, and those contributions truly matter. The donations help support the local artists and musicians that bring these events to life and ensure we can keep the good times rolling for years to come.

Here are the Chicago street festivals not to miss this summer 2026.

May street festivals in Chicago

As the weather warms up, Chicago neighborhoods begin to buzz with the first of the year’s street festivals. Kick off summer with fests celebrating German culture, local music, and Chicago’s iconic hot dogs.

Lincoln Park Mayfest (May 15 – 17): Located in the heart of Lincoln Park, this festival features trendy boutiques, renowned restaurants, and stunning historic architecture.

Howard Street Carnaval (May 16): Howard Street comes alive during the annual African Caribbean Diaspora celebration. This cultural experience includes a parade with dazzling costumes and live DJs, alongside authentic food vendors.

Belmont-Sheffield Music Fest (May 22 – 24): Kick off summer in Lakeview at the festival’s 40th anniversary edition. There will be tribute bands, delicious eats, and a curated mix of local vendors.

Randolph Street Market Festival (May 23 – 24): The urban vintage market is kicking off the season with the 23rd annual Garden Party featuring 200+ antique dealers, live music, and an expanded food court.

Mayfestiversary (May 23 – 24): Hosted by two local breweries, this festival features over 60+ beers, showcasing 20+ local bands, food vendors, and activities for all ages.

Do Division Street Fest (May 29 – 31): Enjoy a diverse lineup of live music on two stages, food, shopping, and family-friendly activities in the bustling Wicker Park neighborhood.

Windy City Hot Dog Fest (May 29 – 31): Vote for your favorite frankfurter at this neighborhood festival that will feature some of Chicagoland’s most iconic hot dog stands in a friendly summer competition.

Maifest Chicago (May 29 – 31): The Lincoln Square festival brings food, dancing, and as always German Gemutlichkeit. Live music and entertainment all days of the event.

The Magnificent Mile Arts Festival (May 30 – 31): The art fest showcases the original art of 60 juried artists from around the country in a variety of mediums, as well as painting and photography.

Explore more: Find even more fests in the full Chicago festival and event calendar.

June street festivals in Chicago

In June, the outdoor events begin in earnest with fun and free festivals filling neighborhood streets and parks every weekend of the month. Mark your calendars for lively art fairs, a celebration of Puerto Rican culture, and the city’s iconic Pride celebrations.

Lincoln Park Greek Fest (June 5 – 7): Food, fun, and OPA. Enjoy all the aromas, sounds, taste, and traditions of Greece in Chicago.

Ribfest Chicago (June 5 – 7): One of the city’s most anticipated food fests is celebrating 26 years in the North Center neighborhood. This barbecue extravaganza features ribs from 20+ vendors.

57th Street Art Fair (June 6 – 7): The 79th annual fair is located in the historic Hyde Park neighborhood. This is the place to buy art and listen to Blue’s music.

Puerto Rican Festival (June 11 – 14): The four day Humboldt Park festival brings the vibrant spirit of Puerto Rico to Chicago. Enjoy mouth watering food, thrilling rides, performances, local art, and cultural showcases.

Andersonville Midsommarfest (June 12 – 14): The traditional Swedish celebration brings 80,000+ people to enjoy eclectic music, great vendors, food, and free kid activities.

Old Town Art Fair (June 13 – 14): This festival offers 200+ nationally acclaimed artists, a garden walk, live music, food court, and a children’s corner.

Wells Street Art Festival (June 13 – 14): The 51st annual festival features over 100 talented artists, delicious food, and great live music.

Taste of Randolph (June 19 – 21): The West Loop festival is known for stellar bands, food, and various shopping vendors.

Fiesta Back of the Yards (June 19 – 21): Enjoy a weekend of live entertainment, carnival rides, Latin cuisine, games, and more showcasing the rich culture of the Back of the Yards community.

Chicago Pride Fest (June 20 – 21): This annual street festival showcases LGBTQ culture in the landmark Northalsted neighborhood. Catch drag performances, a pet parade, and over 150 food and merchandise vendors.

Gold Coast Art Fair (June 20 – 21): The prestigious art fair features over 200 juried artists from across the country. The festival is set between the Art Institute and Lake Michigan and offers live music, drinks, and a variety of food.

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

Chicago Taco & Tequila Fest (June 26 – 27): The festival is taking over Wrightwood Park in Chicago. Sink your teeth into authentic street tacos, premium tequilas, and live music.

Millennium Art Festival (June 27 – 28): Join 110+ artists just steps away from Millennium Park for a day of live music, food trucks, and stunning art.

July street festivals in Chicago

Savor the summer at an array of foodie events, like festivals dedicated to burgers, tacos, and more. And don’t miss exuberant cultural celebrations showcasing African and Chinese heritage.

African/Caribbean International Festival of Life (July 3 – 5): Kick off July with pure vibes on the South Side. Expect Afro-Caribbean beats, bold flavors, and vendors bringing the heat from across the diaspora.

Taste of Chicago (July 8 – 12): The 46th annual festival at Grant Park features iconic Chicago food, international cuisine, live music, and family friendly activities.

Square Roots (July 10 – 12): Lincoln Square’s cozy, folksy block party. Craft beer, indie vibes, family fun, and local vendors that make you want to stay all weekend.

Chosen Few Picnic (July 11): The world’s longest-running house music festival. Over 40,000 people dancing, celebrating, and honoring Chicago’s house legacy.

Southport Art Fest (July 11 – 12): Northside charm meets creativity. Artists, boutiques, restaurants, and theaters spill into the streets for a colorful weekend.

Tacos y Tamales Festival (July 17 – 19): This lively festival in the Pilsen neighborhood offers endless authentic food options, street cantinas, live music, dance, and a variety of vendors.

Roscoe Village Burger Fest (July 17 – 19): The 19th annual Windy City tradition brings together top eateries serving up their juiciest burgers.

Taste of River North (July 17 – 18): The popular neighborhood street festival features local food, live music, and entertainment.

Fiesta Del Sol (July 23 – 26): The 54th annual fiesta returns with live music, entertainment on multiple stages, local and regional food vendors, carnival rides, and more.

Wicker Park Fest (July 24 – 26): The weekend will feature a stellar lineup of 50+ local and nationally recognized artists performing original music, a pet fest, kid friendly spaces, and local food vendors.

Taste of Lincoln Avenue (July 24 – 26): The annual festival offers an amazing lineup of bands, local food favorites, whisky tasting, kids carnival, dog parade, and more.

Chinatown Summer Fair (July 25 – 26): The 46th annual outdoor festival is a true celebration of far East beauty and culture. The festival features food, art, and music located along Wentworth Avenue. Admission is free.

Chicago Italian Beef Festival (July 31 – Aug. 2): The festival is taking over Jefferson Memorial Park and features Chicagoland’s favorite restaurants serving up their unique take on the iconic sandwich.

August street festivals in Chicago

Round out festival season with exciting events across the city. Check out food festivals showcasing Greek, Italian, Mexican, and Polish cuisines, plus fests dedicated to art, music, and more.

Bronzeville Smooth Jazz Fest (Aug. 1): Experience the rhythm of Bronzeville with a celebration of music, culture, and community.

Northalsted Market Days (Aug. 7 – 9): This massive street festival celebrates the LGBTQ+ community in the historic Northalsted neighborhood. Enjoy all day lineups of 250+ vendors, food and drink, dance exhibitions, and more.

Taylor Street Little Italy Festival (Aug. 13 – 16): Chicago’s historic Little Italy is the highlight of this festival. Enjoy Italian cuisine, culture, shopping, and more.

Glenwood Avenue Arts Fest (Aug. 14 – 16): Rogers Park becomes a living canvas during this annual arts fest, with local artists, live music, and community energy.

Lakeview Taco Fest (Aug. 21 – 23): Prepare your taste buds for a taco fiesta, featuring traditional and creative dishes from local eateries.

West Loop Art Festival (Aug. 22 – 23): Fulton Market transforms into a gallery without walls. From emerging creators to seasoned pros, it’s a vibrant stroll through Chicago’s creative pulse.

Taste of Greektown (Aug. 28 – 30): Celebrate 36 years of Hellenic pride in Chicago’s Greektown neighborhood. This festival features Mediterranean flavors, live music, and plenty of Old World charm.

September street festivals in Chicago

Summer may be winding down, but festival season isn’t over yet. Wrap up the season with these fun neighborhood events, including several popular Oktoberfest celebrations.

Taste of Polonia (Sept. 4 – 7): The largest Polish fest in the country, Taste of Polonia features non-stop music, dance performances, and delicious Polish cuisine and beer.

German-American Oktoberfest (Sept. 11 – 13): Lincoln Square is the place to be for Oktoberfest. Try authentic food and traditional drinks while live music from German bands.

Printers Row Lit Fest (Sept. 12 – 13): For more than four decades, this annual literary showcase has taken over the South Loop neighborhood to showcase literature, culture, and community.

Ravenswood Art Walk (Sept. 12 – 13): Explore one of Chicago’s most creative communities during this outdoor arts market featuring 80+ local makers, two stages of live music, a pop-up beer garden, kids activities, food trucks, and more.

Retro on Roscoe (Sept. 18 – 20): Head to Roscoe Village for this throwback extravaganza featuring live music, classic car shows, vintage shopping, and old-school fun for all ages.

Lakeview East Festival of the Arts (Sept. 19 – 20): This popular art festival showcases, live demonstrations, entertainment stages, and family activities in this lakefront enclave.

St. Alphonsus’s Oktoberfest (Sept. 25 – 27): Say “prost!” at this popular Oktoberfest celebration in Lakeview with a craft beer tasting, live music, and a family activity area.

Hyde Park Jazz Festival (Sept. 26 – 27): The South Side festival will be celebrating its 20th anniversary featuring a diverse group of local and international musicians.

If you’ve never been to a cabaret show, Chicago is a great place to start. 

With a 100-plus year history rooted in the city’s early jazz clubs and nightlife, the local cabaret scene has evolved into a diverse community of singers, musicians, actors, storytellers, interdisciplinary artists, directors, and producers who collectively stage hundreds of shows each year.

Learn more about the city’s storied cabaret scene, from Chicago Cabaret Week to top venues to check out.

What makes a show a cabaret?

Cabaret is its own thing. It’s not quite a concert, not quite theatre, and not quite stand-up. 

But cabaret does borrow from many art forms, with a mix of musical numbers and storytelling. It can also include dance, puppetry, magic, or visual arts and other theatrical elements.

What really makes the Chicago scene special is the range of voices and variety of musical styles — including jazz, blues, swing, pop, comedy, spoken word, Broadway, and burlesque — and the performers who reflect the city itself: connecting their life experience and musical interests in a creative way.

History of Chicago cabaret

Chicago’s cabaret scene took off in the early 1900s during the Ragtime era, when dancing and nightlife were booming. These venues quickly became places where people from different backgrounds could mix — something pretty unusual at the time — and they were among the first spots where women could drink in public.

From the start, Chicago’s cabarets were influenced by the famous café-style nightlife of Montmartre in Paris — intimate, edgy spaces that mixed music, conversation, and a little bit of rebellion. That spirit translated easily to Chicago’s fast-growing, anything-goes urban culture.

By the 1910s and 1920s, cabarets thrived in three main areas of the city: the downtown Loop, Towertown on the Near North Side, and the South Side’s Bronzeville and Levee District.

Towertown, an enclave around Michigan Avenue’s historic Water Tower, became the city’s bohemian hub — full of artists, radicals, and nightlife seekers. The Dill Pickle Club captured that vibe perfectly, blending performances, lectures, and late-night socializing.

On the South Side, Bronzeville’s “black and tan” clubs were just as important, bringing together Black performers and mixed audiences during segregation and helping shape early jazz culture.

Then came Prohibition, which hit the scene hard. A late-1920s crackdown wiped out jobs for hundreds of performers, and even after repeal in 1933, strict regulations kept many clubs from recovering.

Cabaret made a comeback after World War II, especially around Rush Street, where clubs like Mister Kelly’s drew major stars. Later, smaller venues like Gentry of Chicago carried the tradition forward.

Today, cabaret in Chicago still reflects its roots — part Parisian inspiration, part local grit — continuing as an intimate, ever-evolving slice of the city’s nightlife.

Chicago cabaret venues

In Chicago, cabaret happens everywhere — and honestly, the space you pick can shape the night just as much as the performer.

You might end up in a small, tucked-away spot like The CheckOut or Stars & Garters, where it feels like you’ve discovered something a little under the radar. Or you could land at Rhapsody Theater, a retro 1921 theater with cabaret seating, great cocktails, and the kind of sound that makes you want to lean in and stay awhile.

If you’re in the mood for something a little more polished, PianoForte Chicago has that clean, concert-style vibe — beautiful instruments, great acoustics, everything dialed in. On the flip side, The Newport Theatre (named “Best Venue for Burlesque 2025” by the Chicago Reader) brings a bit more edge, with cabaret performances that can get bold, playful, and a little unpredictable.

Want something more low-key? Haven really does feel like a haven, with a cozy and welcoming atmosphere. Hey Nonny leans more into the music side, with a mix of cabaret, jazz, and singer-songwriter energy. And Epiphany Center for the Arts, set inside a beautifully restored 19th-century church, is one of those spaces that just feels special the second you walk in.

For something that feels very Chicago, Le Piano hits that sweet spot between cabaret and jazz club — intimate, a little moody, and full of personality. And if you like the idea of dinner with your show, there are plenty of spots around the city where you can settle in with a meal and let the performance unfold around you. It’s an easy, unhurried way to spend an evening.

And then there are the piano bars, which are kind of the heartbeat of it all. Places like The Redhead Piano Bar have been doing this for decades, with singers and pianists taking requests, playing standards, and keeping things loose and social. It’s a different energy — less “sit quietly and watch,” more “be in the moment and enjoy it.”

The takeaway? There’s no “correct” venue. Some are elegant, some are casual, some are theatrical, and some feel like a party. Part of the fun is trying different spaces and seeing how the atmosphere shapes the experience.

Types of cabaret shows

Pick any night of the week and any area of the city, and you’re likely to find a cabaret show. You might walk into a solo show, where one performer carries the entire evening — singing, storytelling, and shaping a clear emotional arc. These shows can be autobiographical, historical, or built around a theme (love, identity, a specific artist, or even a moment in time).

Other nights, you’ll find duos or trios, where performers share the spotlight. These shows often play with harmony, chemistry, and contrast, with different voices and perspectives, and sometimes even a bit of friendly banter.

Then there are ensemble shows, showcase performances, special events, and open mics where multiple artists take the stage, each bringing their own style. At piano bars, audiences can request certain songs and sing along with the music.

Where to find cabaret shows in Chicago

Ready to dive into the local cabaret scene? These are some of the best places to keep track of what’s playing:

• Chicago Cabaret Professionals 
• Working In Concert
• Choose Chicago events calendar

And every May, you can experience a curated introduction to the cabaret scene with Chicago Cabaret Week, which brings together performers and venues across the city for an unforgettable stretch of shows. This year’s Cabaret Week will feature more than 50 performers from May 8 through 17, 2026.

What to expect at a cabaret show

Cabaret audiences tend to be attentive but relaxed. You don’t need to dress up (unless you want to), and you don’t need to know the material ahead of time. Just show up ready to listen.

Sit close if you can. Order a drink. Let yourself lean into the experience.

Because at its core, cabaret is about connection. It’s a performer sharing something meaningful, in real time, with a room full of people who are right there with them.

And once you experience that kind of closeness, it’s hard not to want more.

Chicago’s summer event calendar is overflowing with cultural happenings. From groundbreaking art exhibits to exciting theatrical premieres, there’s truly something for everyone to enjoy.

Check out our list of can’t-miss arts and culture events, grab your tickets, and start looking forward to your jam-packed summer in Chicago.

Theatre and dance performances

Chicago Cabaret Week
May 8 – 17, 2026
Citywide

Kick off summer with Chicago’s dynamic cabaret scene. This annual festival features top cabaret artists at venues across the city, with discounted tickets for $30 or less.

Chicago Dance Month
June 2026
Citywide

This month-long celebration brings dance performances across genres to venues throughout the city. The month kicks off with a free event at Navy Pier featuring local dance companies.

Catch As Catch Can
June 4 – July 12, 2026
Steppenwolf Theatre

A prodigal son returns to blue-collar New England, setting off a spiraling crisis for two families. This Chicago premiere features an all-star ensemble cast, led by Gary Cole. 

Theater of the Mind
Now playing through July 12, 2026
Reid Murdoch Building

From the mind of David Byrne of Talking Heads fame, this immersive production blends neuroscience research with thought-provoking creativity. Guests are led through interactive rooms in small groups for a unique, intimate experience.

The Notebook: The Musical
Aug. 4 – 16, 2026
James M. Nederlander Theatre

The Notebook, presented by Broadway in Chicago, comes to life on stage with this stunning musical adaptation. The show features music and lyrics by multi-platinum singer-songwriter Ingrid Michaelson.

Muddy Waters
June 20 – July 29, 2026
Black Ensemble Theater

As part of its 50th season, Black Ensemble Theater in Uptown presents this ode to Muddy Waters, known as the father of Chicago blues music.

More live theatre and dance in Chicago this summer:

• Deeply Rooted Dance Theatre (May 30, 2026) at The Auditorium 
• Suffs (July 7 – 19, 2026) at CIBC Theatre
• & Juliet (July 22 – Aug. 2, 2026) at The Auditorium
• Water for Elephants (June 23 – July 5, 2026) at James M. Nederlander Theatre
• Brokeback Mountain (May 28 – June 28, 2026) at Chicago Shakespeare Theatre 
• Chicago SummerDance (July – August 2026) in city parks

Live music

Chicago Blues Festival
June 4 – 7, 2026
Millennium Park

Enjoy world-class blues at one of Chicago’s most legendary music festivals, drawing hundreds of thousands of fans from all over the country.

Jazzin’ at the Shedd
May 27 – Sept. 2, 2026
Shedd Aquarium

Bring some fun to your weeknights with this summer series at the Shedd Aquarium, featuring live jazz on the terrace, cocktails, and unbeatable skyline views every Wednesday.

Grant Park Music Festival
June 10 – Aug. 15, 2026
Millennium Park

A Chicago summer tradition for more than 90 years, the Grant Park Music Festival is the nation’s only free, summer-long outdoor classical music series.

Millennium Park Summer Music Series
June 15 – Aug. 6, 2026
Millennium Park

This free outdoor concert series features top local and touring acts, all with a skyline backdrop in downtown Millennium Park.

Chosen Few Picnic
July 11, 2026
Jackson Park

House music fans flock to lakefront Jackson Park for the Chosen Few Picnic, the nation’s longest-running house music celebration.

More live music events and festivals in Chicago this summer:

• Tuesdays on the Terrace (seasonal) at the Museum of Contemporary Art
• The Lyrical Lemonade Summer Smash (June 12 – 14) at Seatgeek Stadium
• Michelada Fest (June 26 – 28) in Union Park
• Windy City Smokeout (July 8 – 12, 2026) outside United Center
• Chicago Gospel Music Festival (July 24 – 25) in Millennium Park
• Lollapalooza (July 30 – Aug. 2, 2026) in Grant Park
• Chicago House Music Festival and Conference (Aug. 27 – 30, 2026) in Millennium Park
• Chicago Jazz Festival (Sept. 3 – 6, 2026) in Millennium Park

Events and openings

James Beard Awards
June 15, 2026
Lyric Opera House

The culinary world’s most prestigious honors will be handed out to chefs and restaurants during a Chicago ceremony. An exclusive tasting event featuring the city’s top chefs will follow the awards.

Obama Presidential Center
Opens June 19, 2026
Hyde Park

The highly anticipated Obama Presidential Center will be opening its doors to the public over Juneteenth weekend. Come explore the interactive exhibits, observation deck, community gardens, public events, and more.

The Hand & The Eye
Opens April 18, 2026
Gold Coast

The Hand & The Eye is a new, only-in-Chicago experience that has transformed the historic McCormick Mansion into the world’s largest magic venue. Guests are invited to wander multiple floors and rooms, each offering a unique performance and dining experience. 

Chicago 250
All year long
Citywide

Chicago 250 is part of the nationwide celebration commemorating the 250th anniversary of the United States. The city will mark the momentous occasion with an array of exhibits, concerts, performances, and more.

Route 66 Centennial
All year long
Citywide

This year marks the 100th anniversary of Route 66, the iconic road trip route that officially begins in the heart of Chicago. Experience the history and legacy of the famous byway with celebrations and events all summer long.

Art exhibits

Willem de Kooning Drawing
June 14 – Sept. 20, 2026
Art Institute of Chicago

The Art Institute of Chicago will stage the first-ever exhibition to spotlight the drawings of Willem de Kooning, the famed American artist and a central figure of the abstract expressionism movement. 

Dancing the Revolution: From Dancehall to Reggaetón
April 14 – Sept. 20, 2026
Museum of Contemporary Art Chicago 

Dancing the Revolution will explore the dynamic genres of dancehall and reggaetón through contemporary art. The exhibit will include paintings, sound sculptures, videos, and other disciplines — all exploring dance as a tool of resistance and liberation.

Anne Frank: The Exhibition
Opens May 1, 2026
Griffin Museum of Science & Industry 

Step inside a meticulous full-scale reconstruction of the Annex where Anne Frank and her family hid for two years during the Nazi occupation of the Netherlands. This moving experience features never-before-seen artifacts from Anne Frank’s life.

Pokémon Fossil Museum
Opens May 22, 2026
Field Museum

Pokémon Fossil Museum will make its North American debut at the Field Museum this summer. This family-friendly exhibition blends the world of Pokémon and paleontology. Guests can compare Pokémon fossils to real-life dinosaurs and ancient life forms.

Paris in Black: Internationalism and the Black Renaissance
Now open
The DuSable Black History Museum and Education Center 

Explore the experiences of Black artists in Europe, particularly Paris, as they sought a refuge for creative expression. The Paris in Black collection explores almost a century of Black art, including stories from iconic figures like Josephine Baker, James Baldwin, and more.

Stingray Touch
May through September
Shedd Aquarium

This one-of-a-kind experience allows visitors to dip their hands into the tropical waters of the seasonal Stingray Touch. Gently touch stingrays as they glide by and discover their unique texture as you learn more about these interesting creatures. 

More Chicago art exhibits to check out this summer:

• Ornament & Information (April 10 – July 19, 2026) at the Chicago Cultural Center
• Tangible Sound: Arrival to a Higher Ground (April 25 – Sept. 27, 2026) at the Chicago Cultural Center
• Crafting Character: The Costumes of Paul Tazewell (open through Sept. 7, 2026) at Griffin Museum of Science & Industry 
• Palomar (Part 1& 2) (May 1  – July 12, 2026) at The Renaissance Society
• Impressions of a City: Drawings by Marvin Young (April 9 – Aug. 23, 2026) at the Intuit Art Museum
• Images of Faith: 3,000 Years of Spiritual Expressions in Mexico (April 24 – Aug. 16, 2026) at the National Museum of Mexican Art

For a century, the illustrious history of Route 66 has captured the American imagination. More than a highway, the so-called “Mother Road” is an open‑road promise stretching from the Midwest to the Pacific — and it all begins in Chicago.

Chicago has been the official starting point of Route 66 since the iconic byway was commissioned in 1926. Over the years, the road has become a bucket-list experience for road trippers, history lovers, and anyone looking to immerse themselves in classic Americana.

In 2026, Chicago is honoring the 100th anniversary of Route 66 with a year-long centennial celebration honoring the past, present, and future of the Mother Road. Learn more about this historic route, including how it got its start, its evolution over the years, and how you can experience it for yourself.

How Route 66 came to be

Route 66 emerged at a moment in U.S. history when the country was shifting from railroads to automobiles as its primary mode of travel.

Cyrus Avery, a member of the Federal Highway System planning committee in the 1920s, argued that a Chicago‑to‑Los Angeles route would stimulate commerce and support the nation’s growing automobile culture.

He pushed for a diagonal roadway that would connect the Midwest to the Pacific, stitching together small-town main streets and existing local roads into a single, continuous path.

The result was a 2,448‑mile ribbon of asphalt running from Chicago to Los Angeles. Today, Avery is widely regarded as the “Father of Route 66.”

Why Route 66 begins in Chicago

When Route 66 was commissioned in 1926, Chicago was the natural choice for its eastern terminus. At the time, the city was an essential crossroads for railroads, highways, and waterways. Travelers headed west already funneled through Chicago, making it the ideal gateway to the Great Plains and beyond.

The original Route 66 began downtown at Jackson Boulevard and Michigan Avenue, a central location chosen for its connection to the city’s early road network. From there, the highway wound southwest through neighborhoods, industrial corridors, and small towns that would soon become iconic stops on the Mother Road.

The heyday of the Mother Road

The golden era of Route 66 stretched from the 1930s through the 1950s.

During the Dust Bowl, thousands of families used the road to flee westward in search of opportunity. More than half a million people left the southern Great Plains states during the 1930s, with most heading to California.

The Grapes of Wrath, John Steinbeck’s famous 1939 novel, followed the Joad family as they traveled west along Route 66. Just one year later, the story was adapted into a major Hollywood film starring Henry Fonda, cementing Route 66’s place in American cultural memory.

After World War II, booming car culture transformed the highway into a symbol of freedom and adventure. In the 1950s, Route 66 became a staple for vacationers headed to California and road trippers looking for adventure.

Soon, the route boomed with mom-and-pop establishments, including diners, gas stations, and motels to service the boom in travelers. The many sights and roadside attractions along the route became an important part of the tourism experience as people headed west.

Explore more: Fuel up for your journey with our guide on where to eat on Route 66 in Chicago.

The Mother Road continued to loom large in pop culture, including a starring role in Route 66, a major TV series that ran from 1960 to 1964. Films like Easy Rider and Thelma & Louise used Route 66 to convey themes of escape and transformation. And the road was forever immortalized by the song “(Get Your Kicks on) Route 66”, first recorded by The King Cole Trio.

By the 1970s, the rise of the Interstate Highway System made Route 66 increasingly obsolete, and in 1985 it was officially decommissioned. Many towns along the route declined as traffic shifted to faster, straighter freeways.

Yet nostalgia, preservation efforts, and a renewed fascination with Americana have sparked a remarkable revival. Today, Route 66 enjoys a second life as a heritage corridor celebrated by travelers, historians, and communities who have restored vintage landmarks and embraced the road’s mythic status in American culture.

Route 66 and the Green Book

During Route 66’s heyday, Black Americans traversing the route often had a vastly different experience than white travelers.

Across the eight states the highway traversed, segregation shaped every aspect of travel. Many gas stations, motels, cafés, and rest stops refused service to Black motorists, forcing them to plan trips with caution.

During this time, Black travelers relied on the Negro Motorist Green Book. Published from 1936 to 1964, this guide listed hotels, restaurants, service stations, and more across the country that would serve Black customers. Green Book locations on Route 66 were an essential lifeline for Black motorists in this era.

The Green Book boosted Black‑owned businesses along Route 66 and provided crucial information for safe passage. Green Book sites near Route 66 in Chicago still standing today include:

• Navy Pier
• Art Institute of Chicago
• Field Museum
• Adler Planetarium
• Shedd Aquarium
• Chicago Cultural Center
• Soldier Field
• Hilton Chicago

The guide also included many other Chicago locations, including a variety of sites throughout the city’s historic Bronzeville neighborhood.

Chicago’s original Route 66 alignment

Route 66 was officially commissioned in 1926, the same year Chicago was booming with new skyscrapers, jazz clubs, and industries like steel and meatpacking.

From its historic downtown starting point, Route 66 followed a path that many Chicagoans still recognize today:

• Jackson Boulevard and Michigan Avenue heading westbound
• Ogden Avenue through the Near West Side
• Southwest along Ogden toward Cicero and Berwyn
• Continuing through suburban towns like Lyons, McCook, and Joliet

This alignment connected travelers to the city’s industrial might, immigrant neighborhoods, and bustling commercial districts, offering a first taste of the cultural diversity that defines the entire route.

The Navy Pier centennial starting point

In 2026, Chicago officially recognized Navy Pier as the centennial starting point of Route 66. The designation is meant to celebrate the 100th anniversary of the route, symbolizing how Route 66 continues to evolve while honoring its roots.

For visitors, starting at Navy Pier offers a spectacular sense of arrival: the glittering lake, the skyline rising behind you, and the promise of 2,448 miles of Americana stretching ahead.

This spring and summer, Navy Pier will host a full slate of Route 66 centennial celebrations, including classic car displays, family-friendly festivals, and live performances. Visitors can find the complete schedule on Navy Pier’s official events calendar.

Iconic Route 66 stops in Chicago

Chicago’s stretch of Route 66 brims with landmarks that blend history, architecture, and pure nostalgia. Here are some must‑see stops for visitors beginning their journey — and make sure to check out our full Route 66 Chicago itinerary for more ideas.

1. Navy Pier centennial starting point

Chicago’s lakefront gem is a lively, family‑friendly destination with restaurants, rides, and public art. Snap a photo with the brand new Route 66 sign at Navy Pier before setting off on your journey.

2. Original Route 66 Begin sign

This classic sign at the intersection of Jackson and Michigan remains a pilgrimage spot for travelers and photographers. It’s a reminder of the road’s original alignment and a symbol of Chicago’s role in American road‑trip culture.

3. Lou Mitchell’s

A Chicago institution since 1923, Lou Mitchell’s has long been known as the “first stop on the Mother Road.” The pancakes, donut holes, omelets, and “world’s best coffee” have fueled countless Route 66 adventures.

4. The Berghoff restaurant

One of Chicago’s oldest restaurants, The Berghoff has been serving German classics since 1898. Chicago’s first post-Prohibition liquor license proudly hangs behind the bar. Stop in for a pint and a pretzel, then snap a photo with the iconic neon marquee out front.

5. Route 66 mural

As you begin your Route 66 journey, make sure to pull over at Lulu’s Hot Dogs. This retro spot sports a large-scale Route 66 mural that depicts some of the iconic spots on this list.

As Route 66 celebrates its 100th anniversary, Chicago remains the place where the adventure begins. No matter how far you’re planning to travel, you’re stepping into a century‑long tradition of exploration, freedom, and discovery.

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 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!

April is a jam-packed month in Chicago — spring is on the horizon, tulips start to bloom all over the city, and weekends fill up with endless food, drink, cultural, musical, and free events.

From the start of baseball season and spring flower shows to major art fairs and film festivals, there’s no shortage of fun to be had in the city this month.

Check out our top picks for things to do in Chicago throughout the month of April.

Top events in Chicago this April

White Sox home opener (April 2): Baseball season kicks off on the South Side as the White Sox take the field against the Toronto Blue Jays. Catch more home games throughout the month.

EXPO ART WEEK (April 7 – 12): Leading up to EXPO CHICAGO, art lovers can catch an array of community events and installations in neighborhoods throughout Chicago.

EXPO CHICAGO (April 9 – 12): This top international art fair returns to Navy Pier with more than 130 leading galleries from across the globe.

Chicago Cubs home games (through April): The beloved Cubs have returned to Wrigley Field to start another exciting season in their historic ballpark.

Art on THE MART (April 9): This nightly art and light installation returns to the riverfront, kicking off with a dynamic original show by an internationally acclaimed artist.

CIVL Fest (April 16 – 25): This citywide music fest puts a spotlight on the city’s most beloved independent music venues, including stages large and small.

Chicago Latino Film Festival (April 16 – 27): For more than four decades, the film festival has hosted screenings highlighting filmmakers from Latin America, Spain, Portugal, and beyond.

House Party at the Shedd Aquarium (April 18): Dance to local DJs at this high-energy house music event inside Chicago’s historic lakefront aquarium.

One of a Kind Show (April 24 – 26): Shop over 300 talented artists, makers, and designers showcasing their work and handmade goods for one weekend only at the Merchandise Mart.

International Jazz Day (select dates in April): Chicago is proud to be the official host city of International Jazz Day. The heart of this year’s celebration is a global all-star concert at the Lyric Opera, bringing over 40 iconic jazz artists to one stage.

Spring Flower Show at Garfield Park Conservatory (through April): Step into a lush indoor oasis during “Showers of Flowers”, featuring 80 hanging baskets of trailing vines and colorful flowers.

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

More events in Chicago this April

Dozin’ with the Dinos (April 3 and 10): Families can spend a night inside the Field Museum with after-hours access to exhibits, hands-on activities, and plenty of dino encounters.

South Loop Easter Egg Hunt (April 4): This egg hunt will include more than 20,000 eggs hidden around Chicago Women’s Park and Gardens, alongside plenty of treats, activities, and even a visit from the Easter Bunny.

Chi-ibigan Food Festival (April 4): Come taste the very best of Chicago’s red-hot Filipino food scene, including top spots like Kasama, Bayan Ko, Del Sur, and more.

Chicago Fire FC vs. Nashville SC (April 4): Experience the unbeatable energy of Soldier Field during a Chicago Fire home match.

Center Days at Hyde Park Art Center (April 4): This free family-friendly series at the Hyde Park Art Center includes exhibits and art-making activities for kids of all ages.

Green City Market (starts April 4): The Green City Market in Lincoln Park returns for the spring season, bringing together dozens of the Midwest’s best farms and food vendors.

Windfall at Steppenwolf Theatre (starts April 9): This gripping new play from Academy Award-winning Tarrell Alvin McCraney explores family dynamics, grief, justice, and the spirit of activism.

Impressions of a City: Drawings by Marvin Young (Starts April 9): The Intuit Art Museum hosts a new exhibition featuring whimsical drawings that capture the city’s architecture, energy, and everyday moments from a lifelong South Side resident.

The Other Art Fair (April 9 – 12): Experience a different kind of art fair at Artifact Events with over 100 independent artists, alongside live performances, DJs, and cocktails.

Chicago Electronic Music Festival (April 11): This one-day music fest will take over the historic Ramova Theatre in Bridgeport with DJs, live performances, panels, and workshops.

Chicago Tea Festival (April 11 – 12): This two-day festival in the Jefferson Park neighborhood will highlight all varieties of tea, with samples, workshops, cupping sessions, and more.

Chicago Mahogany Tours (through April): Dive into the hidden histories in Chicago’s historic South and West Side neighborhoods, including Englewood, North Lawndale, Bronzeville, and beyond.

Chicago Artisan Market (April 18 – 19): Shop more than 100 artisans offering food, fashion, art, housewares, and more at this indoor market focused on handmade items.

Greek Independence Parade (April 19): The Greektown neighborhood of Chicago will celebrate the community’s heritage with a procession of traditional costumes, music, performances, and much more.

Pickwick Vintage Show (April 19): Browse curated fashion, accessories, home goods, and much more during this vintage pop-up inside the Chicago Athletic Association hotel.

Earth Week at Lincoln Park Zoo (April 20 – 26): Celebrate Earth Day all week long at the Lincoln Park Zoo with free family-friendly activities focused on sustainability and wildlife conservation.

CineYouth Festival (April 24 – 26): Now in its 21st edition, CineYouth is Cinema/Chicago’s annual film festival celebrating filmmakers 22 and younger from around the world.

Alvin Ailey American Dance Theater (April 24 – 26): This legendary dance company is coming to The Auditorium, featuring classic works from the Ailey repertory.

Doc10 Film Festival (April 25 – May 3): The acclaimed all-documentary film festival returns to Chicago with a lineup of powerful films, along with filmmaker Q&A and special events.

Chicago Bulls at the United Center (various dates): Catch the iconic basketball team play on their home court all month long.

Madama Butterfly at Lyric Opera (through April 12): Be swept away by the classic tale of Madama Butterfly with a stunning new production breathing fresh perspective into an age-old story.

Hamilton (through April 26): The blockbuster musical returns to Chicago for a limited run at Broadway in Chicago’s CIBC Theatre.

Crafting Character: The Costumes of Paul Tazewell (through April): Learn the secrets behind the iconic costumes of Hamilton, Wicked, and beyond.

Glow Wild at Brookfield Zoo (through April): This new evening event features an array of glowing handcrafted lanterns, plus live performances and unique food experiences.

Chicago Humanities Spring Festival (through April): The annual Chicago Humanities Festival brings together over 60 luminaries and artists for conversations, performances, and gatherings.

Martin Wong: Chinatown USA (through April): The newest exhibit at the unique Wrightwood 659 space features vivid depictions of New York’s Chinatown, highlighting themes of community and identity.

Matisse’s Jazz: Rhythms in Color (through April): The newest exhibit at the Art Institute showcases the bold, colorful world of artist Henri Matisse and his iconic cut paper works.

Balloon Museum: Emotion Air (through April): This immersive exhibit is made up of larger-than-life balloon art installations that transform air into interactive sculptures and plenty of photo-worthy moments.

National Poetry Month events (through April): The Chicago Public Library will honor the art and impact of poetry with special events and workshops at branches throughout the city.

1. Watch the first summer fireworks show

May 23, 2026
The Navy Pier summer fireworks kick off for the season on Memorial Day weekend. This beloved tradition is the perfect way to celebrate the start of summer in Chicago.

The weekly shows take place on Wednesdays at 9 p.m. and Saturdays at 10 p.m. through Labor Day weekend. The breathtaking display is accompanied by a soundtrack of popular music, with special themed nights for holidays.

2. Enjoy a free museum day

All month long
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 for Illinois residents this May 2026:

• Art Institute of Chicago: May 21 after 5 p.m.
• Field Museum: Every Wednesday
• Museum of Contemporary Art: Every Tuesday after 5 p.m.
• Shedd Aquarium: Every Tuesday after 5 p.m.
• Chicago History Museum: May 6, 20, 25
• DuSable Black History Museum and Education Center: Every Wednesday
• Adler Planetarium: May 6, 13, 20, and 27

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

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

3. Shop the Maxwell Street Market

Sunday, May 17, 2026
The open-air Maxwell Street Market has been a Chicago 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 market is a representation of the neighborhood’s deep cultural roots, which has been shaped by generations of immigrants. It was also a crucial incubator for the Chicago blues scene. Come experience a true piece of Chicago history. 

4. Attend a free workout at Millennium Park

Saturdays starting May 16, 2026 
Grab your mat and head to Millennium Park for a free weekend fitness class.

These outdoor workouts are held on the Great Lawn every Saturday morning this summer. Get your heart pumping with pilates, yoga, cardio, kickboxing, Zumba, and more.

Check the full schedule for Millennium Park Summer workouts. And find more free events coming to Millennium Park this summer, like the Millennium Park Summer Film Series and the Millennium Park Summer Music Series.

5. Celebrate Mexican culture at Navy Pier

May 1 – 3, 2026m
Immerse yourself in Mexican culture during Mexico Fest at Navy Pier.

This free event will feature live music and dance performances, a curated marketplace experience, and fun free workshops. Events include performances from local groups like Ballet Folklorico de Chicago, Mariachi Mexicanísimo, Grupo Rimel, and more.

Explore more: Delve further into Mexican culture and cuisine in Chicago’s international neighborhoods like Pilsen and Little Village (known as the “Mexico of the Midwest”).

6. Watch Buckingham Fountain switch on for the summer

May 9, 2026
Kick off summer with a spectacular Chicago celebration. During the free Switch on Summer event, the city marks the start of the season by turning on the city’s iconic Buckingham Fountain in Grant Park.

One of the largest fountains in the world, Buckingham Fountain is known for its ornate design and evening light and music displays.

The event, which takes place on Saturday, May 9, will also include family-friendly activities and free performances from local dance, music, and cultural groups.

7. Honor Asian American Heritage Month

All month long
Asian American and Pacific Islander Heritage Month is the perfect time to explore the rich cultural contributions of the city’s diverse Asian communities.

Check out some of the free celebrations happening this month:

• Free admission at Heritage Museum of Asian Art (May 8): Enjoy free admission to this fascinating museum showcasing Asian art, with complimentary tours, wine, and appetizers.
• Chinese Folk Dance (May 9): See folk dancing performances at the Rogers Park library by a youth dance troupe, featuring lion and lotus dances.
• Dot Art Inspired by Artist Yayoi Kusama (May 13): In Kenwood, this children’s craft event is inspired by the iconic works of Yayoi Kusama.
• Wednesday Night Improv with Stir Friday Night (May 20): Catch an all-ages improv set from this acclaimed Asian American comedy troupe.
• Origami Workshop (May 21): Learn the art of Japanese paper folding at this free workshop, where attendees will learn basic origami designs.

Explore more: Find more things to do during Asian American and Pacific Islander Heritage Month.

8. Attend the Chicago Memorial Day Parade

May 23, 2026
Honor those who made the ultimate sacrifice this Memorial Day with the City of Chicago Memorial Day Wreath Laying Ceremony and Parade.

The ceremony will start at 11 a.m. in Daley Plaza, followed by the parade at noon. The parade route will proceed south on State Street from Lake Street to Van Buren Street.

9. Browse a local farmers market

All month long
May is the start of farmers market season in Chicago! The city’s many free markets are filled with local vendors selling handmade goods, seasonal produce, ready-to-eat meals, and more. Many neighborhood markets also offer free live music, performances, storytimes for kids, and workout classes.

• The Wicker Park Farmers Market kicks off its outdoor season on Sunday, May 3, with free kid-friendly activities, pilates, yoga, new local vendors, and more.
• The 61st Street Farmers Market opens for the season on Saturday, May 16, just a few blocks from Jackson Park in the Hyde Park neighborhood.
• The Lincoln Square Farmers Market pops up in the heart of this charming neighborhood on Tuesdays and Thursdays.
• The iconic Green City Market in Lincoln Park is now open every Saturday and Wednesday, overflowing with fresh produce and local favorite bakeries.

Explore more: Check out more farmers markets happening in neighborhoods all around Chicago.

10. Hit the beach

Starting Memorial Day weekend
Chicago’s scenic Lake Michigan shoreline stretches for 26 miles, dotted with more than two dozen sandy beaches perfect for swimming, sunbathing, and enjoying the stunning views.

Beach season officially begins on Memorial Day weekend, when Chicago’s free beaches will be open for the public to enjoy.

People-watch at North Avenue Beach, take in the views at South Shore Beach, play some beach volleyball at Foster Beach, rent paddleboards at 31st Street Beach, and beyond. Most Chicago beaches are connected via the Lakefront Trail, an 18-mile path for pedestrians to run, walk, and bike.

Explore more: Check out more sandy spots to explore with our Chicago beach guide.

Bonus! Explore a new neighborhood

Whether you’re a first-time visitor or a long-time resident, there’s always something new to discover in Chicago. Get to know a new neighborhood on a free Chicago Greeter tour, led by a friendly local who will show you each neighborhood’s landmarks, hot spots, and hidden gems.

For example, experience an urban melting pot in West Ridge, featuring plenty of international grocers and authentic restaurants. Become immersed in the historic communities of Washington Park and Woodlawn, which are home to a lively art scene, must-try eateries, and an abundance of landmarks. Or take a cultural journey with an immersive visit to the historic Chinatown neighborhood.

Looking for more? Check out our guide on free things to do in Chicago all year long.

EXPO CHICAGO Contemporary Art Fair returns to lakefront Navy Pier from April 9 – 12, 2026 with an exciting roster of 130 leading galleries from around the world to Chicago.

This annual event celebrates contemporary and modern art with a diverse schedule of exhibits, discussions, and installations. This year’s main event will take place in Navy Pier’s Festival Hall, with additional programs and events throughout Chicago.

Highlights of the 2026 EXPO CHICAGO event include:

• Visitors will get an early preview of the Obama Presidential Center ahead of its public opening this June with an exhibit inspired by the Center’s art and architecture.
• Discussions featuring luminaries like Nick Cave, Kahil El’Zabar, Hans Ulrich Obrist, Elizabeth Alexander, and more.
• The debut of EXPO Projects, showcasing impactful presentations and activations from non-profits and other organizations on the fair floor.

Get EXPO CHICAGO tickets

About EXPO CHICAGO

Now in its 13th year, EXPO CHICAGO showcases leading contemporary and modern art galleries from across the globe. The show also includes talks and panel discussions, on-site installations, public art initiatives, and other events throughout the city. 

EXPO CHICAGO draws upon the city’s rich history as a vibrant arts destination, while highlighting the latest from the global contemporary arts scene. Leading up to the main event, EXPO ART WEEK bring exhibits and community events into neighborhoods across Chicago.

Featured galleries at EXPO CHICAGO 2026

This year’s exhibitors come to Chicago from more than 30 cities across 15 countries, including Spain, South Korea, Singapore, Portugal, South Africa, Japan, Brazil, France, Taiwan, and more.

EXPO CHICAGO continues its collaboration with the Galleries Association of Korea (Gaok), to present a selection of 12 leading Korean galleries within the fair’s core Galleries section.

Highlights included renowned galleries and collectives such as Regen Projects, Sean Kelly, Anton Kern, Karma, moniquemeloche, Night Gallery, Vielmetter, and beyond.

The EXPO CHICAGO 2026 exhibitor showcase will include:

• Galleries, showcasing leading international exhibitors and special partnerships.
• Focus, highlighting emerging galleries and artistic practices with an emphasis on newer galleries.
• Profile, presenting solo booths and projects by established international galleries.

Explore the full list of participating galleries for EXPO CHICAGO 2026.

EXPO CHICAGO programs

Each year, EXPO CHICAGO presents a full schedule of thought-provoking discussions, installations, and exciting activations. This year’s core programs and events include:

• Dialogues, a series of provocative on-site panel discussions offering a deeper look at some of the themes, artists, and partnerships at the fair.
• Override, a public art initiative that uses digital billboards across the city to showcase works by leading and emerging local and international artists.
• Exchange, conversations about the contemporary art market and its current trends.
• New to EXPO this year, Projects features innovative presentations and initiatives by non-profits, museums, and other cultural organizations.

Curators will find special events like the Curatorial Forum and the free, public Curatorial Conference. EXPO will also present its fifth annual Directors Summit, a multi-day event that gathers emerging and distinguished art museum leaders from around the globe.

EXPO ART WEEK 2026

Leading up to the main event at Navy Pier, EXPO ART WEEK celebrates Chicago’s diverse artistic scene with off-site programming and events all around the city from April 7 – 12, 2026.

Check out a few of this year’s highlights:

• South Side Night (Tuesday, April 7): The official kick-off event for EXPO Art Week showcases venues and galleries in the historic Hyde Park neighborhood and beyond.
• Art After Hours (Friday, April 10): Enjoy extended evening hours at galleries across the city, featuring receptions, artist talks, and more.

Tickets for EXPO CHICAGO Contemporary Art Fair are now on sale. Choose from single-day and three-day admission options, along with a limited number of opening night tickets. Guided tours and discounted tickets for students and seniors are available.

Black history tours of Chicago offer an engaging journey through the city’s rich African American culture.

Embark on an in-depth exploration of influential neighborhoods like the city’s “Black metropolis” and landmark institutions such as the nation’s oldest independent African American history museum.

These tours tell the stories of Black pioneers, artists, activists, and community builders who helped shape Chicago’s cultural and historical landscape. Discover tours of Chicago that explore the city’s Black history through the lens of food, culture, music, and more.

Chicago Mahogany Tours

The popular Chicago Mahogany Tours are led by Chicago’s own TikTok-famous urban historian, Sherman “Dilla” Thomas. Each bus tour covers a different Chicago neighborhood, including historically Black communities such as Bronzeville, Englewood, Pullman, Chatham, and more. Through his deep knowledge of local history and pride in his community, Dilla shines a spotlight on Chicago’s people, architecture, and impact on the world. Participants will also learn about inventions and innovations that originated in Chicago, exemplifying Dilla’s motto — “everything dope about America comes from Chicago.”

The Black Foodies

This husband and wife duo (married for more than 30 years) are known as The Black Foodies, with a mission of spotlighting the city’s diverse Black-owned and operated restaurants. Their often sold-out Taste and Tour Chicago bus tours cover both historic landmarks and top dining destinations. Expect a culinary journey complete with tastings of signature dishes as you learn about the cultural significance of the cuisine and hear the stories behind the restaurants. While on board the luxury coach bus, guests can enjoy Chicago trivia, prizes, and a lively atmosphere.

Gone Again Travel & Tours

This African American-owned travel agency in Chicago’s Austin neighborhood has specialized in Black heritage travel for more than 25 years. They also host the Chi-Town Soul Trolley, which offers a unique view of the city’s historic West Side. Guests travel to landmark sites, such as the Epiphany Center for the Arts and former Black Panther meeting spots, and visit local restaurants that showcase the city’s soul food scene. This tour is a great way to experience the rich history and culture of Chicago’s West Side while enjoying a delicious meal.

Pullman National Historical Park

As the birthplace of the Black labor union and Chicago’s first National Park, the Pullman neighborhood is steeped in history that contributed to America’s framework. Guided tours of this landmark community are available to the public on the first Sunday of the month from May through October. These walking tours share a glimpse of Pullman’s past and highlight the community’s impact on industrial innovation, labor rights, urban planning, and more. Or stop by the Exhibit Hall to grab a brochure and embark on a self-guided tour.

More Black history tours and experiences in Chicago

• Chicago Greeter offers free guided tours of Chicago neighborhoods, led by a friendly local. Tours can be customized based on your preferred language and interest areas.
• The Black Metropolis National Heritage Area is committed to honoring the legacy of Bronzeville, Chicago’s historic “Black metropolis.” Check the schedule for public tours and events or request a private neighborhood tour.
• Willie Dixon’s Blues Heaven Foundation is the keeper of a piece of music history. They offer tours of the legendary Chess Records building, showcasing the rich heritage of American blues music.
• Chicago Architecture Center offers walking and bus tours that explore almost every corner of the city. The schedule includes many options with ties to Black history, like tours of the historic Hyde Park and Bronzeville neighborhoods.
• Inside Chicago offers public and private tours of Chicago’s most fascinating areas. The Chicago’s “Black Metropolis”: Bronzeville Neighborhood Tour is available for private bookings from small groups.