Want to know what’s happening this weekend in Chicago? Look no further. There’s a whole calendar of exciting events, exhibits, and activities taking place all over the city this month in Chicago.

A few of highlights this Halloween weekend in Chicago include:

• The 30th annual Haunted Halsted Halloween Fest in the Northalsted neighborhood
• Kid-friendly happenings like Slightly Spooky Saturday at Navy Pier and Not So Scary Halloween Party at the Bronzeville Children’s Museum
• Fun Halloween shows like The Rocky Horror Picture Show, Jekyll & Hyde, and The Séance
• Tons of Halloween parties, pop-ups, and events all over the city.

Check out just a few of the events and happening in Chicago this weekend, Oct. 30 – Nov. 1, 2026.

Oct 31

Haunted Halsted Halloween Fest & Parade

This year marks the 30th anniversary of the Haunted Halsted Halloween Parade and to celebrate, we’re making it an all-day affair! Have a ghoulish good time with food, drinks, music, local vendors, live performances and more! That then leads directly into Chicago’s only Halloween Night parade, where more than 300 costumed participants show off their creativity and Halloween spirit!

• 12:00pm: Haunted Halsted Fest Begins
• 7:00pm: Halloween Parade
• 8:00pm: Costume Contest & Post-Parade Party

Event details

Saturday October 31, 2026

Northalsted

Oct. 31

The Rocky Horror Picture Show

THE ROCKY HORROR PICTURE SHOW returns to The Chicago Theatre on Halloween night! Experience the cult-classic phenomenon in a new 4K restoration with a live…

Loop

Event details

Saturday October 31, 2026

The Chicago Theatre
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614

Oct. 31 – Nov. 1

Terror in the Tropics: Midnight in Mexico

This Halloween, Three Dots and a Dash is taking over Salon 61 for Terror in the Tropics: Midnight in Mexico, a one-night-only celebration of Mexico’s…

Event details

Oct. 31 – Nov. 1, 2026

Salon 61
61 W Hubbard St

Oct. 31

Haunted House Party at Shedd Aquarium

Join Shedd Aquarium for a frightfully fun night at Haunted House Party, where house music and Halloween collide. Come dressed in your creepiest, kookiest costumes…

South Loop

Event details

Saturday October 31, 2026

Shedd Aquarium
1200 S. Lake Shore Dr.

Oct. 30 – Nov. 1

Pilsen Día de Los Muertos Window Walk

Día de Los Muertos Window Walk The Pilsen Chamber of Commerce is excited to welcome you to Pilsen’s 18th Street commercial corridor to marvel at…

Event details

Oct. 30 – Nov. 1, 2026

18th Street commercial corridor
West 18th Street, between Damen Ave and Halsted St.

Oct. 30 – 31

DEATH TOLL: The Halloween Drinking Game Sketch Comedy Show

Our longest-running sketch show is back again to scare you into drinking! DEATH TOLL is a sketch comedy show with one simple rule: drink when…

Event details

Oct. 30 – 31, 2026

Cornservatory
4210 N Lincoln Ave

Oct. 30 – 31

Sanctum Dark Music Festival 2026

The Sanctum Dark Music Festival returns to Chicago for Halloween weekend on Friday, October 30, and Saturday, October 31, 2026. The darkwave, industrial, and post-punk…

Pilsen

Event details

Oct. 30 – 31, 2026

Thalia Hall
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614

Oct. 30 – 31

Vampire Playlist – Destinos: 9th Chicago International Latino Theater Festival

Vampire playlist by Concrete Content. Written by Xitlali Celeste, Angelica Davila, Pedro Arturo Jimenez, Luis Antonio Mora, Cielo Santiago Muñoz, Amelia Roque, Dani Suarez, Erik Ventura,…

Event details

Oct. 30 – 31, 2026

El Schomburg
2538 W. Division St.

Nov. 1

Día de los Muertos at Navy Pier

Join us at Navy Pier on Saturday, November 1 for Día de los Muertos, featuring art, cultural experiences and activities celebrating this meaningful tradition. Honor…

Streeterville

Event details

Sunday November 1, 2026

Navy Pier

Oct. 30

Devil’s Daughter

The hottest show in town, Devil’s Daughter, features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Lincoln Park

Event details

Oct. 30, 2026

iO Theater
1501 N. Kingsbury St.

Oct. 30 – 31

Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour

“Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime” is a 2-hour afternoon/evening walking tour that uncovers Chicago’s shadowy past through chilling tales…

Event details

Oct. 30 – 31, 2026

Inside Chicago Walking Tours
Starting location given upon ticket purchase

Oct. 30 – 31

City Cruises Chicago Seadog Haunted River Tour

As Halloween season arrives, the Seadog Haunted River Tour returns to the Chicago River, offering guests a hauntingly fun journey through the city's storied past.…

Event details

Oct. 30 – 31, 2026

City Cruises Chicago – Navy Pier
600 E Grand Ave

Oct. 31

Slightly Spooky October at Navy Pier

Join us for free movies at Navy Pier in Crystal Gardens on Saturdays, October 17 and 24, plus trick-or-treating throughout the Pier on Halloween, October…

Streeterville

Event details

Oct. 17 – 31, 2026

Navy Pier

Oct. 30 - Nov. 1

Fright at the Field

Spooky season has arrived at the Field Museum! Join us for Fright at the Field, a Halloween experience featuring the return of Underground MISAdventure, and…

Event details

Oct. 19 – Nov. 1, 2026

The Field Museum
1400 S Lake Shore Dr,

Oct. 31

Howl-O-Ween Pet Costume Contest

Plan your costumes, pack up your pets, and join us at Harry Caray’s Navy Pier for our annual Howl-O-Ween Pet Costume Contest benefiting PAWS Chicago!…

Event details

Saturday October 31, 2026

Harry Caray’s Navy Pier
700 East Grand Avenue

Oct. 31

Not So Scary Halloween Party

Create your own Halloween Arts & crafts. Halloween Costume Parade. Halloween Spooky Story & More!!! Stop by for a THRILLER TIME!!!!!

Event details

Saturday October 31, 2026

Bronzeville Children’s Museum
9301 South Stony Island Avenue

Oct. 31

The Séance: Live (and dead) in Chicago

We play with the dead. The Séance returns to Chicago's Stars & Garters for Saturday nights this fall. Recreating the atmosphere and techniques of 19th-century…

Event details

Oct. 31, 2026

Stars and Garters Theater
3914 N Clark St

Oct. 30 - Nov. 1

Creepy Cruise

From strange sightings to eerie haunts, mobsters and more, our latest nighttime tour takes you into Chicago's shadowy past. Cruise along the Chicago River as…

Event details

Oct. 2 - Nov. 1, 2026

Chicago’s First Lady Cruises
112 E Wacker Drive

Oct. 30 – 31

The Cosmic Underground Show

Step aboard for a one-of-a-kind journey where mind-reading, magic, comedy, and sci-fi collide in ways you won’t find anywhere else in Chicago. Hosted by real-life…

Event details

Oct. 30 – 31, 2026

cosmic underground theater
3433 W Fullerton Ave

Oct. 30 - Nov. 1

Fall Fest at Lincoln Park Zoo

Chicago’s favorite free and family-friendly festival is back at Lincoln Park Zoo for another season of harvest-time fun! From September through October, stop by the…

Lincoln Park

Event details

Sept. 25 – Nov. 1, 2026

Lincoln Park Zoo
Chicago

Nov. 1

Harvest Fest

Join Aville Grows for our first-ever Harvest Fest! Bring your friends, family, and neighbors for a morning of fall fun, festive treats, and community connection.…

Event details

Sunday November 1, 2026

Aville Grows Community Gardens
5339 N Ashland Ave

Nov. 1

Fashion Film Festival Chicago

Stories We Wear: Fashion as Visual Narrative Join Fashion Film Festival Chicago and the Chicago History Museum for an afternoon exploring fashion as a powerful…

Lincoln Park

Event details

Sunday November 1, 2026

Chicago History Museum
1601 N. Clark St.

Oct. 30 - 31

INCREDIBLE INSECTS: Interactive Live Bug Exhibit

This Halloween season, join us for the third year of Incredible Insects at The Butterfly House at Navy Pier: an interactive exhibit featuring wacky and…

Event details

Oct. 1 - 31, 2026

Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States

Oct. 30 – Nov. 1

The Book Of Mormon

The Book of Mormon is returning to Chicago for a limited limited engagement from Friday, October 23 through Sunday, November 1, 2026. From the creators…

Loop

Event details

Oct. 30 – Nov. 1, 2026

Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601

Oct. 30 – Nov. 1

Don Giovanni

The path to damnation never sounded so sweet The 2026/27 Season kicks off with a thrilling fable of deceit and retribution. Sharp humor, high drama,…

Loop

Event details

Oct. 30 – Nov. 1, 2026

Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606

Explore our events calendar for more Chicago events and happenings.

Please note that all events are subject to change.

The holiday season in Chicago is always an exciting time. With countless events across multiple neighborhoods, there are so many ways to celebrate.

One of the biggest holiday events of the year is The Wintrust Magnificent Mile Lights Festival — which also happens to be the largest nighttime parade in the United States and the third-largest parade in the country.

This classic Chicago celebration is a packed day of free, family-friendly activities leading up to the famous tree-lighting parade on Michigan Avenue. Many Chicagoans consider this event the official kickoff to the holidays.

Here’s a guide to everything you need to know about the 35th annual Lights Festival in Chicago, which promises to be bigger and better than ever before.

When is The Wintrust Magnificent Mile Lights Festival?

This year’s Lights Festival will be held on Saturday, Nov. 21, 2026.

The festival kicks off with Lights Festival Lane from 11 a.m. to 4 p.m. The evening tree-lighting parade steps off at 5:30 p.m., followed by a spectacular fireworks display at 7:30 p.m.

Here’s a quick overview of The Wintrust Magnificent Mile Lights Festival 2026 schedule:

• Lights Festival Lane at Pioneer Court (11 a.m. – 4 p.m.)
• Evening parade on Michigan Avenue (starts at 5:30 p.m.)
• Fireworks on the Chicago River (approximately 7:30 p.m.)

Where to watch The Wintrust Magnificent Mile Lights Festival?

The parade starts at Oak Street and Michigan Avenue and travels south, ending at Wacker Drive just after the DuSable Bridge.

Tip: For the best parade viewing, head to the east side of Michigan Avenue, especially on the north end of the parade route. It’s less crowded than areas closer to the river.

The fireworks will be held near the DuSable Bridge, with spectators lining Wacker Drive.

Lights Festival Lane is located in Pioneer Court at 401 N. Michigan Ave.

Can’t see it in person? The Lights Festival will air on ABC7 Chicago on Sunday, Nov. 22 at 6 p.m., with on-demand access throughout the holiday season.

What is The Wintrust Magnificent Mile Lights Festival?

The annual winter celebration, a local tradition for more than 30 years, marks the beginning of the holiday season in Chicago with an all-day holiday extravaganza.

The festivities kick off with the outdoor Lights Festival Lane where families can explore an interactive wonderland of holiday-themed activities. The free-admission fest is held during the day on Saturday. It includes photos with Santa Claus, live performances, tasty treats, and more family-friendly activities.

The festival is followed by the grand tree-lighting parade on Saturday evening that brings the illumination of over one million lights along Michigan Avenue (also known as The Magnificent Mile, one of Chicago’s most famous streets). The procession includes:

• Grand Marshals Mickey Mouse and Minnie Mouse leading the procession
• Marching bands from around the country
• Dozens of glittering holiday floats 
• Giant helium balloons, including tons of classic characters
• Music performances by local and national artists
• Santa Claus himself on the grand finale float to welcome the holiday season

The evening finishes with a stunning fireworks display over the Chicago River.

Explore more: Discover even more family-friendly holiday fun in Chicago.

What restaurants are close to the parade route?

Looking to grab a bite to eat before or after the Lights Festival? Here are a few top spots to eat near the parade route:

Family-friendly restaurants 

• Lou Malnati’s Pizzeria
• Harry Caray’s 7th Inning Stretch
• Sweetwater Tavern & Grille
• Gino’s East
• Gordon Ramsay Burger
• Eataly
• Giordano’s Famous Stuffed Pizza 
• The Walnut Room

More spots to eat near the parade

• Nic + Junior’s
• Friends Sushi on Rush
• ETA Restaurant + Bar
• Joe’s Seafood, Prime Steak & Stone Crab
• LIA TAVERN
• American Craft Kitchen & Bar
• About Last Knife (ALK)
• Land & Lake Kitchen

How can I get to and from the festival?

You can take a car or ride share, but keep in mind that there may be traffic and limited parking. If you’re driving to the festival, note that North Michigan Avenue closes to traffic between Oak Street and Wacker Drive as early as 3 p.m. on Saturday. The DuSable Bridge will also close as early as 3 p.m. on Saturday.

You can also take the CTA Red Line train to the festivities. The Grand and Lake stops are both near the festival and the parade route, and the Chicago stop is just a few blocks from the parade. There are also several CTA bus lines that can get you close to the action. Keep in mind that bus routes are also affected by road closures.

Thursday, Nov. 26, 2026
State Street 

The Chicago Thanksgiving Parade, a local tradition for more than 90 years, kicks off the holiday season with a fun-filled morning in the heart of downtown Chicago.

More than 25,000 spectators are expected to gather downtown for the procession. The family-favorite event was even named the #2 Thanksgiving parade in the country by Time Out.

Learn more about this year’s parade and start planning your unforgettable Thanksgiving Day in Chicago.

What is the Chicago Thanksgiving Parade?

The annual parade takes over Chicago’s iconic State Street in the Loop on Thanksgiving morning. Watch the colorful procession make its way north from Ida B. Wells Drive to Randolph Street.

Originating in the 1930s, the parade was created to help lift spirits during the Great Depression. The free, all-ages event continues to be a cherished holiday tradition to this day.

Each year, live entertainment includes the country’s top marching bands, live music, festive floats, acrobats, equestrians, cultural performances, celebrity guests, and larger-than-life helium balloons.

When is the Chicago Thanksgiving Parade?

The 92nd annual Chicago Thanksgiving Parade will take place on Thanksgiving morning: Thursday, Nov. 26, 2026, from 7:45 a.m. to 10 a.m. CT.

Where to watch the Chicago Thanksgiving Parade?

The procession will travel north on Chicago’s historic State Street, stepping off at Ida B. Wells Drive and continuing on to Randolph Street.

The route will pass by iconic Chicago landmarks, like the Chicago Theatre marquee and Macy’s On State Street.

Make sure to get there early to get a prime spot along State Street. Or opt for the VIP tickets for guaranteed seating with great views, along with warm drinks and private restrooms.

The parade will be covered live on CBS Chicago at 8 a.m. to 10 a.m. The parade will wrap up as CBS kicks off coverage of the Chicago Bears vs. Detroit Lions game at noon on Thanksgiving Day.

Explore more: Looking for more things to do on Thanksgiving Day in Chicago? Check out our guide to Thanksgiving dinner in Chicago.

How to get to the Chicago Thanksgiving Parade?

If you plan to drive, book your parking near the route in advance with apps like SpotHero. Keep in mind that there will be street closures and detours near the parade route.

You can also take public transportation to the parade. There are several CTA bus and train lines that offer stops near the parade route. Keep in mind that bus routes are also affected by road closures.

A few of the CTA ‘L’ train stops within easy walking distance of the route include:

• Harold Washington Library (Brown, Orange, and Pink Lines)
• Jackson (Red and Blue Lines)
• Monroe (Blue Line)
• Clark and Lake (Brown, Green, Orange, Blue, and Pink Lines)

Chicago Thanksgiving Parade 2026 highlights

The 2026 parade promises to be unforgettable, with a diverse lineup of entertainment from all over the country.

Grand Marshal: Charles “Peanut” Tillman, a Chicago Bears legend, will lead this year’s parade.

Giant helium balloons: Led by Teddy the Turkey, the parade’s official mascot, you’ll see a cast of familiar and much-loved faces, from the Grinch to Cookie Monster to Rudolph and friends.

Marching bands: An annual favorite, watch groups from high schools and universities from Chicago and all over the country.

Festive floats: These fun and colorful floats will showcase local groups and arts organizations.

Equestrian units: See miniature horses, rodeo groups, and animal therapy programs.

Special performances: Cheer on cultural groups, school districts, dance troupes, arts groups, drum lines, acrobats, and beyond along the parade route.

Santa Claus: Santa himself will close out the parade in a brand-new sleigh.

Chicago goes all out for the holidays, with something magical happening in every corner of the city. The season kicks off with the Christmas Tree Lighting Ceremony (a tradition for over a century) and things stay festive through the city’s spectacular New Year’s Eve celebrations.

Visitors can expect charming holiday markets, trees covered in twinkling lights, tons of fun seasonal events, and even a decked-out holiday train led by Santa and his elves that soars through the city.

If you’re looking for the perfect holiday getaway, this itinerary hits some of the classic Chicago experiences (like ice skating in the shadow of The Bean and shopping at a downtown Christmas market) along with a few off-the-beaten-path finds in Chicago’s welcoming neighborhoods.

Day one: classic Chicago holiday traditions

Top experiences:

• Art Institute of Chicago
• City of Chicago Christmas Tree
• Christkindlmarket
• Macy’s on State Street
• A holiday show (A Christmas Carol, The Nutcracker)

This is a packed day of top holiday sights, so bundle up and get ready for a magical start to your Chicago visit.

Start your day at the Art Institute of Chicago, the city’s world-class art museum. Spend some time wandering the museum’s many galleries, filled with priceless works and some of the world’s most famous paintings. The Impressionism gallery is particularly impressive. If you’re looking for the greatest hits, this guide tells you what to see in an hour.

Insider tip: Head to the museum entrance on Michigan Avenue to see the iconic bronze lions adorned with giant Christmas wreaths.

When you leave the museum, walk north up Michigan Avenue until you see the giant Christmas tree standing tall in Millennium Park. The massive tree shines brightly from mid-November through early January. Snap a photo, then walk a bit into the park to say hello to “The Bean” dusted in snow.

Insider tip: There’s skating in your schedule for tomorrow, but the Millennium Park ice rink and the unique Skating Ribbon are both nearby if you’re looking for more time on the ice.

Next, walk a few blocks west to Christkindlmarket Chicago. One of the city’s most beloved holiday traditions, Christkindlmarket is a bustling outdoor bazaar in the style of an authentic Christmas market. Grab a souvenir mug of hot cocoa or mulled wine and wander the booths of sweets, German treats, and handcrafted gifts.

If you have time, pop into the landmark Macy’s on State Street to see the Great Tree inside the Walnut Room.

End the night at a festive holiday show. Get tickets to A Christmas Carol at the Goodman Theatre, a heartwarming classic that’s become a tradition for generations of Chicagoans. Or see a uniquely Chicago spin on The Nutcracker, performed by the Joffrey Ballet at the stunning Lyric Opera House.

Day two: unique traditions on the South Side

Top experiences:

• Museum of Science and Industry
• Midway Plaisance ice rink
• Shopping and dining in Hyde Park

Begin your day at the Griffin Museum of Science and Industry, the largest science museum in the Western Hemisphere.

Alongside hands-on and interactive exhibits, the museum also hosts its annual Christmas Around the World and Holidays of Light. This fun seasonal showcase delves into holiday traditions from around the world with more than 50 decorated trees.

Next, lace up your skates and take a spin at the ice rink of the Midway Plaisance. This scenic spot is set against the dramatic backdrop of the University of Chicago campus.

Spend some time shopping and dining in the heart of Hyde Park. Browse for gifts at unique local businesses like design-focused The Silver Room, the carefully curated Call and Response Books, and mother-daughter-owned Suuri Designs.

Finally, find a warm spot to enjoy dinner and drinks. The award-winning Virtue is an excellent option, with warm Southern flavors and a welcoming atmosphere. Or grab a spot at the bar inside the Sophy Hyde Park, where a large fireplace keeps the vibe cozy.

Day three: rooftop curling and twinkling lights

Top experiences:

• Garfield Park Conservatory
• Curl & Chill at The Gwen
• ZooLights

In the morning, head to the Garfield Park Conservatory. The third-largest garden under glass in the world, the conservatory’s indoor gardens are the perfect serene escape from the hustle and bustle. Take time to admire the annual Winter Flower Show, when the soaring space is filled with festive plants and flowers.

Next, enjoy some friendly competition with a fun winter sport. Each winter, The Gwen Hotel in River North hosts a popular rooftop curling experience on its outdoor terrace. Enjoy seasonal cocktails and a curated menu, try your hand at curling, and warm up at the firepit table.

Afterward, spend some time holiday shopping along The Magnificent Mile, one of the world’s most iconic retail destinations. Admire the winter window displays, pop into stores, and stock up on unique gifts for loved ones (and yourself).

Finally, end your holiday weekend in Chicago with a local favorite — ZooLights at Lincoln Park Zoo. This evening event transforms the historic zoo into a true winter wonderland, with millions of twinkling lights on almost every surface. There will also be live entertainment, festive treats, and, of course, plenty of wildlife to meet. It’s a magical event, and the perfect way to wrap up your holiday weekend in Chicago.

If you’re looking for a getaway in January or February, Chicago continues to deliver a flurry of seasonal fun long after the holidays end.

Between ice skating under the city lights and catching a show on a snowy evening, a winter trip to Chicago turns cold days into warm memories.

Embrace the new year by planning your trip around top winter events, including the 15th annual Chicago Theatre Week, the 20th annual Chicago Restaurant Week, the Chicago Auto Show, and more.

Here’s our guide to planning a magical winter getaway in the country’s Best Big City with top experiences, neighborhood gems, and more.

Day 1: Classic Chicago experiences

Top experiences:

• Art Institute of Chicago
• Skating in Millennium Park
• Winter rooftop bars
• Broadway in Chicago

Your first stop is the downtown Millennium Park Campus, home to some of Chicago’s most recognizable landmarks and attractions.

Start your day at the adjacent Art Institute of Chicago, one of the country’s oldest and largest art museums. The permanent collection features roughly 300,000 pieces of art, including the renowned Impressionism gallery, plus a rotating array of special exhibitions.

Afterward, bundle back up and make your way to Millennium Park for ice skating. Enjoy a spin on the ice at the iconic McCormick Tribune skating rink beneath Cloud Gate (also known as “The Bean”). Another popular spot is Maggie Daley Park’s quarter-mile-long Skating Ribbon, which winds between snow-covered evergreens.

When it’s time to grab a bite, across the street to the historic Chicago Athletic Association. Tucked away on the second floor, the Drawing Room is an ornate vintage space accented by dark wood and leather furnishings. Grab a spot by one of the three crackling fireplaces and enjoy the cozy atmosphere.

Stop by one of Chicago’s winter rooftop bars, where you can admire the snowy skyline views or warm your hands beside a fire pit. Sip seasonal cocktails inside an igloo at the I|O Godfrey, play a round of curling at The Gwen’s rooftop terrace, or admiring the stunning riverfront views at LH Rooftop.

End your evening at the theatre. Broadway in Chicago’s winter lineup includes the Tony-winning rom-com Maybe Happy Ending and smash-hit Oh, Mary!, a gleefully absurd comedy about Mary Todd Lincoln. Or see what’s playing at the city’s neighborhood theatres.

Day 2: A day of art and culture

Top experiences:

• Art and history museums 
• Elegant high tea
• Warm and welcoming dining

Set aside a full day for Chicago’s South Side, a collection of historic neighborhoods filled with hidden gems for art and culture lovers. Spend the morning exploring one of the area’s acclaimed museums, from a massive science center to intimate art galleries.

Delve into Black history, art, and culture from Chicago and around the world at the DuSable Black History Museum and Education Center in Washington Park.

The free Smart Museum of Art features galleries spanning historical and contemporary works, with rotating exhibitions that give you a reason to come back.

If you’re lucky enough to snag tickets, you can explore the new Obama Presidential Center. But even without a ticket, there’s plenty to see and do on the campus. Admire public art, try Obama family recipes, and soak in snow-dusted city views from the Sky Room (limited free tickets are available on a first-come, first-served basis).

In the afternoon, head to the Stony Island Arts Bank. This stunning bank building was once in disrepair but has been lovingly restored and transformed into a community arts space.

Browse the collections and exhibitions, then settle in for a drink or bite to eat. Make reservations for a unique high tea experience at the Korean-inspired Han Cha, or sample creative cocktails and natural wine at Yunomi, a walk-in bar and lounge.

Afterward, stroll through the University of Chicago campus, home to dramatic Gothic buildings that appear even more majestic under the snow. Notable points of interest include the Rockefeller Chapel and the Harper Memorial Library’s grand reading room.

From late November to mid-February, you can skate at the nearby Midway Plaisance ice rink, located on the site of the 1893 World’s Fair. Admission to the rink is free, with skates available to rent for a small fee.

Round out the day in Hyde Park with dinner at Virtue Restaurant & Bar, a James Beard Award-winning kitchen that specializes in Southern cooking. Or enjoy bold flavors from across the African diaspora at welcoming Mahari.

Day 3: Cozy and quirky vibes

Top experiences:

• Lincoln Park Conservatory 
• Local shopping and dining
• Chicago Magic Lounge 

Start your morning in charming Lincoln Park with a sweet French toast flight at Batter & Berries or house-made pastries and Mediterranean dishes at Cafe Yaya.

After brunch, pop into the Lincoln Park Conservatory. The Victorian-era greenhouse provides a delightful dose of greenery in the middle of winter. Admission is free, but book a timed ticket in advance. Right next door, Lincoln Park Zoo is also free year-round. The zoo’s lakefront grounds are particularly beautiful on a frosty day.

Next, spend the afternoon on Clark Street in the quirky Andersonville neighborhood. Lined with unique boutiques and colorful storefronts, this area is known as a mecca for cozy local shopping and dining.

Pick up Chicago-inspired gear and accessories at Transit Tees, then leaf through whimsical stationery, art, and gifts at Foursided. Drop by Cowboys and Astronauts, a pleasantly offbeat store stocked with lifestyle goods and apparel.

After shopping, pop into Simon’s Tavern to warm up with hot glögg, a Scandinavian beverage made with mulled wine or spiced spirits. Also on Clark Street, the Swedish American Museum traces the history of Chicago’s Swedish community.

As the day winds down, grab tickets to the Chicago Magic Lounge. The speakeasy-style venue is hidden inside an old-fashioned laundromat. A rotating cast of magicians performs close-up tricks before taking the stage for astonishing performances.

Afterward, enjoy a nightcap at Nobody’s Darling, an acclaimed cocktail bar that celebrates trailblazing women of color, or Marty’s Martini Bar, an intimate and inclusive LGBTQ+ lounge that’s been pouring a proper martini for more than two decades.

Find more things to do and see in Chicago this winter.

The best way to get to know Chicago is one meal at a time.

This three-day Chicago food itinerary explores the city’s most iconic dishes and under-the-radar restaurants, bakeries, and neighborhood spots that keep locals coming back.

Discover some of the most celebrated restaurants and beloved hidden gems in the country’s Best Big City. Begin with downtown staples before heading into Chicago’s vibrant neighborhoods for dim sum, authentic Mexican fare, Puerto Rican specialties, and more.

Day 1: Sample Chicago classics and must-try bites

Dining highlights:

• Deep dish pizza
• Italian beef
• The original brownie

Enjoy a traditional diner breakfast

Ease into the day with a hearty plate at Lou Mitchell’s, a beloved landmark serving breakfast to locals, visitors, and celebrities for more than a century.

Anticipate a line, fresh-baked pastries, bottomless coffee, and doughnut holes handed out while you wait. Look forward to a heaping plate of fluffy pancakes and stuffed omelets.

From there, walk to Willis Tower and take the elevator to the 103rd floor to experience a bird’s-eye view of downtown from Skydeck Chicago. Perched more than 1,350 feet above the ground, The Ledge’s glass balconies extend beyond the building, giving you a dramatic look at the cityscape.

Grab an Italian beef at a local legend

In River North, get your fill of a Chicago staple at Mr. Beef, the legendary Italian beef stand that inspired The Bear.

Order your sandwich the Chicago way: dipped in savory jus and topped with hot giardiniera or sweet peppers on top. It’s messy, drippy, and exactly the kind of lunch you want when trying one of Chicago’s signature foods.

Afterward, trade the city streets for the river on an architecture cruise with Wendella Tours & Cruises, which runs year-round. The family-owned company has taken passengers along Chicago’s waterways since 1935, with architecture tours showcasing famed historical landmarks, such as the Wrigley Building and Tribune Tower.

Make room for deep dish

Dinner calls for another Chicago classic: deep dish pizza. Iconic pizzerias like Lou Malnati’s and Gino’s East both have downtown locations, while Pequod’s is worth the trek to Lincoln Park if you want to try a local favorite. The caramelized-crust pies have earned a devoted following.

Keep in mind a deep dish pie can take 45 minutes or so to bake, and one is usually more than enough for the table, so order a salad or appetizer and settle in.

Finish with a world-famous dessert

Close out the night at the Palmer House, where you can try the original brownie. Invented at the hotel for the 1893 World’s Columbian Exposition, the decadent baked good remains on the menu at Lockwood Restaurant & Bar. It’s dessert with a side of history. The hotel’s gilded lobby is also the perfect spot for a nightcap.

Day 2: Eat your way through international neighborhoods

Dining highlights:

• Dim sum in Chinatown
• Tacos in Pilsen
• Neighborhood dining in Bridgeport

Begin with dim sum in Chinatown

Take the Red Line ‘L’ train to Cermak-Chinatown to enjoy breakfast in Chicago’s historic Chinatown neighborhood. 

MingHin Cuisine is a Cantonese restaurant that serves Hong Kong-style dim sum throughout the day, so take your time savoring baskets of dumplings, buns, rice rolls, and other small plates. Since dim sum is made for sharing, bring friends and order a bit of everything.

After breakfast, roam through the colorful streets of Chinatown. Walk under the ornate Chinatown Gate on Wentworth Avenue, peruse the gift shops, and look for the bronze zodiac statues at Chinatown Square.

Before leaving, drop by Chiu Quon Bakery, the oldest Chinese bakery in Chicago, for milk tea paired with a coconut cream puff, almond cookies, or a warm Portuguese egg tart.

Check out the top things to do and see in Chinatown.

Wander through Pilsen’s art and food scene

Travel west to nearby Pilsen, where the neighborhood’s creative spirit is proudly on display, from its noteworthy murals to art galleries, boutiques, and colorful storefronts.

Grab lunch at local favorites like La Luna, a colorful and comfortable spot known for its tacos, or Mariscos San Pedro, which serves refined Mexican seafood inside the historic Thalia Hall.

After lunch, explore the free National Museum of Mexican Art, home to one of the largest collections of Mexican art in the country, spanning ancient Mexico through the present.

Pilsen is also known for its thriving coffee shop scene, from new additions like Anticonquista Cafe ot longtime favorites like Cafe Jumping Bean.

Discover more activities and restaurants in Pilsen.

Dig through vintage finds in Bridgeport

Continue on to Bridgeport, home to the Chicago White Sox, a blue-collar streak, and a growing cultural scene.

It’s the ideal location to hunt for vintage clothes, records, furniture, and other secondhand goods before going to dinner. The galleries and studios at Bridgeport Art Center are also worth a visit.

For dinner, book a table at The Duck Inn, housed in a century-old pre-Prohibition tavern. The rotisserie duck is the move, though you may be tempted by the Duck Inn Dog, an upscale take on a Chicago-style hot dog, featuring duck fat and housemade condiments.

After dinner, pop over to the cozy Charis Listening Bar for a nightcap with vinyl spinning in the background.

Day 3: Find the best bites from West Town to the West Loop

Dining highlights:

• A viral breakfast sandwich
• One of the city’s best burgers
• A Chicago-born jibarito

Line up for a wait-worthy breakfast sandwich

By day, Filipino bakery and restaurant Kasama serves creative pastries, Filipino comfort food, and a viral breakfast sandwich (featured on The Bear).

While there may be a line, the savory sandwich is well worth waiting for, especially when paired with one of the bakery’s sweet treats. By night, Kasama showcases an elevated tasting menu that has earned them two Michelin stars.

After breakfast, spend some time exploring West Town, one of the city’s top gallery districts. Chicago Avenue is a good place to start. Look through curious finds at indie boutiques and vintage stores, and discover the gallery scene alongside public art and longtime cultural institutions.

Try the sandwich Chicago invented

Head northwest toward Humboldt Park for a jibarito, the Chicago-born sandwich made with garlicky fried plantains as a stand-in for bread. Try a chicken or steak jibarito at Papa’s Cache Sabroso or La Bruquena, then wander Paseo Boricua on Division Street, the heart of the neighborhood’s Puerto Rican community.

If you still have a sweet tooth, swing by The Original Rainbow Cone in Wicker Park. The family-run Original Rainbow Cone first opened in Chicago’s Beverly neighborhood in 1926, peddling a five-flavor cone layering chocolate, strawberry, Palmer House, pistachio, and orange sherbet.

Grab dinner in the West Loop, a foodie mecca

A former meatpacking district, the West Loop has become one of Chicago’s most highly regarded dining destinations, with Fulton Market and Randolph Street’s Restaurant Row brimming with award-winning restaurants.

For a classic West Loop experience, join the line at Au Cheval for one of the city’s (and maybe the country’s) best burgers. Don’t skip the thick cut bacon or the fried egg on top.

Among the neighborhood’s longtime favorites, avec is where Mediterranean flavors meet Midwestern ingredients in a menu designed around shared plates, while Monteverde brings a global influence to Italian cooking and handmade pasta.

Explore Chicago’s acclaimed dining scene and more places to eat in Chicago.

Chicago is the city that’s Never Done, Never Outdone. And we keep proving it year after year.

In 2026, Chicago welcomed new immersive experiences, celebrated James Beard Award wins, hosted major events — and was voted Best Big City in the U.S. for the tenth year in a row by travelers from all over the world.

But we don’t rest on our laurels. Chicago is always pushing the envelope, which means tons of exciting events, openings, and milestones coming in 2027 and beyond.

New attractions and events in 2026

This was a landmark year for Chicago, filled with top events, major anniversaries, and exciting new additions to the city’s packed lineup of attractions. Here are some of the top moments and milestones for Chicago in 2026.

Openings and re-openings

• Obama Presidential Center: A historic moment for Chicago and the nation, the Obama Presidential Center officially opened this summer on a sprawling lakefront campus in Hyde Park.
• The Hand & The Eye: The world’s largest magic venue opened in Chicago this spring, where guests can discover magic around every corner in a historic mansion.
• F1 Arcade: The sights, sounds, and thrills of F1 are now available in River North, where a new arcade offers state-of-the-art racing simulators in a social atmosphere.
• The Cube: Challenge your friends at this new, competitive experience based on the hit TV show.
• Hello Kitty Cafe: Enjoy ultra-cute treats and merchandise at the world’s largest Hello Kitty Cafe, now open in the heart of downtown.
• Stony Island Arts Bank: This dynamic cultural hub reopened to the public with a new Korean-inspired tea room and chic bar space.
• TimeLine Theatre Company: This award-winning theatre company has a new home, thanks to the recent opening of its new 250-seat, $40 million venue in Uptown.
• Muddy Waters MOJO Museum: The former home of legendary musician Muddy Waters has been transformed into a blues museum.
• Garfield Park Conservatory: The conservatory unveiled its new Children’s Garden, an indoor space with interactive elements and accessibility amenities.

Top moments and milestones

• Chicago’s first-ever Dick Clark’s New Year’s Rockin’ Eve drew thousands downtown to see Chance the Rapper, J. Ivy, and more.
• The Chicago Hounds won their first-ever Major League Rugby championship, capping off the first undefeated season in league history.
• International Jazz Day came to Chicago in April, honoring the city’s rich and enduring contributions to the genre.
• The city hosted top sports events, including the WNBA All-Star Game, the WWE Elimination Chamber, the Presidents Cup, and more.
• Chicago honored the 100th anniversary of Route 66, including naming Navy Pier as the official centennial starting point of the iconic road.
• The city joined in American 250 festivities with special events celebrating the history of Chicago and the United States.

Awards and accolades

• Chicago was named the Best Big City in the U.S. for the 10th consecutive year by the Readers’ Choice Awards, the industry’s longest-running and most trusted awards program.
• Chicago was also named one of the Best Places to Go in 2026 by Frommer’s and a Travelzoo Best Bets destination, highlighting the city as a standout destination for travelers from around the world.
• Jacob Potashnick of Feld won the prestigious James Beard Award for Best Chef: Great Lakes.
• Chicago O’Hare International Airport was named the busiest airfield in the United States, with new direct routes added to top destinations like Tokyo, San Juan, Cairo, Manila, and more.
• West Town was named one of the world’s coolest neighborhoods by Time Out, thanks to a dynamic mix of coffee shops, dining, and galleries.
• Chicago was named the top city in the world for climate change resilience, the only U.S. city in the top 10.

What’s coming in 2027

There’s always something new to discover in Chicago. Mark your calendar for these standout events, openings, and world premieres coming to the city in 2027.

Exciting openings and major renovations

• Candy Hall of Fame Experience: Located on The Magnificent Mile, this experiential attraction will spotlight iconic candies and confectionery history.
• Universal Horror Unleashed: This immersive horror attraction, the first of its kind in the Midwest, will include mazes, themed bars, and exclusive merchandise.
• Bally’s Casino and Resort: This new riverfront casino will include a 500-room hotel, a 3,000-seat entertainment venue, bars and restaurants, riverfront green space, and more.
• Shedd Aquarium: This historic aquarium will unveil a new Changing Oceans exhibit, featuring a walk-through tunnel that immerses visitors in the beauty of a coral reef.
• 360 CHICAGO: Located inside the former John Hancock building, 360 CHICAGO will become Chicago’s first multi-story observation deck, debuting new event space and an extended visitor experience.
• Museum of Science and Industry: A new entrance experience will increase accessibility, add modern amenities, and create public green space overlooking the park’s lagoon.

Upcoming events

• Chicago Restaurant Week: The 20th annual Chicago Restaurant Week will celebrate two decades of dining deals, featuring hundreds of restaurants across the city, from Jan. 22 – Feb. 7.
• Savannah Bananas at Soldier Field: The Banana Ball World Tour is coming to Chicago’s Solider Field on July 10 and 11, 2027.
• 2027 MLB All-Star Game: Chicago’s Wrigley Field will host the MLB All-Star Game on July 13, 2027, the first time for the historic stadium since 1990.
• Pokémon North America International Championships: Pokémon fans will take over McCormick Place from June 18 to 20, 2027, bringing more than $500,000 in prizes.
• Harry Styles at Soldier Field: Harry Styles will bring his “Together, Together” tour to Soldier Field for five nights this summer.
• The Princess Bride: A New Musical: The beloved film, adapted as a musical for the first time, will make its pre-Broadway debut at Chicago’s Nederlander Theatre from July 19 – Aug. 22, 2027.
• Illinoise: The Tony Award-winning dance musical, inspired by the hit Sufjan Stevens album, will return to Chicago Shakespeare Theater in February after a successful Broadway run.

What’s next for Chicago: 2028 and beyond

Chicago is a place of endless innovation and evolution. These transformative projects are creating new experiences and breathing fresh life into historic landmarks.

Exciting projects

• The 78: A major riverfront development, the 78 will include McDonald’s Park, a dedicated soccer stadium that will be the new home for the Chicago Fire FC.
• 1901 Project: This multi-phase project will transform the area surrounding Chicago’s United Center, adding a 6,000-seat entertainment venue, 20+ acres of park space, a 233-room hotel, nearly 10,000 housing units, and restaurant and retail space.
• Water Tower Place: The landmark mall is kicking off its 50th year with extensive renovations, set to redefine the shopper experience by 2028.
• Concourse D: The largest new passenger facility built at O’Hare in more than 30 years will add 19 gates and complete the first phase of the ambitious ORDNext modernization project.
• Avalon Regal: A new South Side landmark is coming back to life, thanks to a meticulous restoration of the intricate Moorish interior.
• Englewood Nature Trail: An unused railroad corridor will become a vibrant public green space, with construction expected to begin next year.
• Hotel Florence: This historic hotel building, located on the grounds of the Pullman National Historical Park, will undergo a total restoration to become an operating boutique hotel by late 2028.

Celebrate cozy weather and changing leaves in the city made for autumn adventures. We’ve got everything you need to plan the perfect fall day in Chicago, whether you’ve got little kids in tow or hard-to-impress teenagers.

Itinerary: Classic Chicago family day

Hit some of Chicago’s most iconic downtown spots, then head a bit north to explore a historic free zoo.

Morning: Downtown parks and the Art Institute of Chicago

Start at Maggie Daley Park, where whimsical play gardens and fall‑colored trees make the whole space feel magical. Take the meandering bridge to Millennium Park, where kids can see their reflection in “The Bean.”

Next, walk to the kid-friendly Ryan Learning Center at the Art Institute of Chicago for free drop‑in art studios and hands‑on projects. Or get a ticket and head inside to see pint-sized exhibits like the Thorne Miniature Rooms, featuring exquisitely detailed, dollhouse‑sized historic interiors.

Lunch: Aster Hall and The Magnificent Mile

Head north to 900 North Michigan Shops and settle into Aster Hall, where families can choose from an array of options, including ramen, burgers, pastries, or seasonal treats — perfect for picky eaters.

Afterward, stroll down iconic Michigan Avenue, known as The Magnificent Mile, for window shopping and family-friendly attractions. Some favorite stops for all ages include the beloved American Girl Chicago, the Harry Potter Shop, the Museum of Ice Cream, the world’s largest Starbucks, and more.

Afternoon: Lincoln Park Zoo

Take the short bus or cab ride to Lincoln Park Zoo, where cooler temperatures mean more active animals and fall foliage along every path. The annual Fall Fest is a family favorite, when the historic zoo is filled with festive decorations, a pumpkin patch, live music, professional pumpkin carvers, and more.

If the kids still have energy to burn, stroll a short stretch of the nearby Lakefront Trail for crisp breezes and skyline views.

Itinerary: Neighborhood explorer day

Spend a day discovering hidden gems, from unique cultural experiences to some of the city’s best bites.

Morning: Palmisano Park and sweet treats

Head to the Bridgeport neighborhood and stop at a local spot like Fat Peach Bakery for coffee and inventive pastries.

Next, walk through Palmisano Park, a former limestone quarry turned into a peaceful escape with its winding paths, tall grasses, and elevated views of the city. See if you can spot the many turtles that enjoy catching rays here on floating logs.

Lunch: Chinatown

Enjoy lunch by sharing a cozy, bubbling hotpot at Qiao Lin in Chinatown, where everyone can pick their own veggies, meat, and noodles to cook right at the table.

Afterward, take a walk around Chinatown and enjoy the colorful shops and ornate architecture. Stop for a bubble tea or an afternoon treat from Chiu Quon Bakery, the oldest bakery in Chinatown.

Afternoon: Pilsen murals and Day of the Dead

After Chinatown, continue to the nearby Pilsen neighborhood, a hub for art, dining, and Hispanic culture.

This vibrant enclave is home to the free National Museum of Mexican Art. Each autumn, the museum’s annual Día de los Muertos exhibition showcases the roots of this meaningful holiday with ofrendas, folk art, and vibrant tributes that are both educational and moving.

Itinerary: Adventure‑seeking teens and tweens

Teens and older kids will love this action-packed itinerary, with a fun comedy show and a high-speed boat ride on the lakefront.

Morning: Jack’s Pumpkin Pop-up

Jack’s Pumpkin Pop-up is Chicago’s largest fall festival, taking over Goose Island all October long. Run through the city’s largest corn maze, enjoy fall bites and sips from food trucks, and check out classic carnival games.

All ages are welcome, and the pop-up is especially family-friendly during the day on weekends. Plus, teens and tweens will love all the photo opportunities throughout the decorated space.

Afternoon: Boat cruise

Hop on a fall boat cruise aboard the unforgettable Chicago Seadog for skyline views framed by autumn foliage.

Book the classic Lakefront Speedboat Ride for an exhilarating cruise along the scenic shoreline. For teens looking for something spooky, the early evening Haunted River & Lake Tour will dive into some darker Chicago history, from ghost stories to real gangsters.

For boat cruises that go later into fall, check out some of the classic Chicago architecture cruises.

Early evening: Magic or comedy

End the day with tickets to a show they won’t be able to stop talking about.

Head to Logan Square, where the Cosmic Underground specializes in immersive and hilarious magic, mind-reading, and sleight of hand. Audience members must be 13 or older. In downtown, The Magic Parlour is a long-running show that welcomes kids age 12 and up.

Or check out ComedySportz, a fast-paced show that turns comedy into a competitive game. The content is geared for audiences of all ages, so the whole family will have a blast.

Itinerary: Toddler and preschooler fall fun

Enjoy a day of sensory experiences, from a dedicated children’s museum to an immersive play space inspired by nature.

Morning: Navy Pier and Chicago Children’s Museum

Start your day at Navy Pier, an all-ages destination right on the Chicago lakefront.

Head straight to the Chicago Children’s Museum, a perfect fall stop for little ones. Spaces are built for climbing, touching, imagining, and exploring. In the current Zoom Room exhibit, kids can play with race cars while learning basic science concepts.

Outdoor afternoon: Japanese garden and a new playground

Drive south to Jackson Park for a quiet, stroller‑friendly walk through the manicured grounds. Make sure to check out the Osaka Garden, filled with lush Japanese landscaping. Kids will love the bridges, koi ponds, and the maple trees turning brilliant red and orange in October. It’s a peaceful oasis right in the city.

Nearby, the new Obama Presidential Center campus is a sprawling green space where kids can run and play. The nature-inspired playground is open to the public, no ticket needed.

Indoor afternoon: Garfield Park Conservatory

If the weather calls for some time indoors, make a beeline to the Garfield Park Conservatory. This glass-covered wonderland is filled with flowers, cacti, ferns, and exotic plants from all over the world.

Wander through the themed rooms and make a stop at the newly reimagined Children’s Garden. The fully indoor play space blends nature, science, and imagination with fully accessible and sensory-friendly elements. Make sure to include the Children’s Garden when you buy your ticket.

Check out more kid-friendly things to do in Chicago all year round.

It’s an incredible time to be a Chicago sports fan. Almost all of the city’s iconic sports teams are still playing, whether the season is just kicking off or the playoffs are heating up.

Come cheer on the Chicago White Sox, Chicago Bears, Chicago Blackhawks, Chicago Bulls, Chicago Stars, and the Chicago Fire. Plus, check out unique sports experiences like stadium tours and an interactive sports museum.

If you’re looking to get in on the action this fall, check out this bucket list for sports fans in the country’s Best Big City.

Root for the White Sox in the playoffs

Chicago White Sox fans have been blessed (by Pope Leo, maybe?) with an unbelievable season of baseball, leading up to their sweep of the Houston Astros during the Wild Card Series. Now, the White Sox are facing off against the Cleveland Guardians in the American League Division Series.

The Sox will play a crucial Game 3 on Wednesday, Oct. 7 as they continue their historic post-season push. Tickets for games at Rate Field are in high demand, and fans will be packed into bars on the South Side and beyond.

Chicago White Sox fall schedule

• Wednesday, Oct. 7: White Sox vs. Cleveland Guardians (Rate Field)
• Thursday, Oct. 8: White Sox vs. Cleveland Guardians (Rate Field, if needed)
• Saturday, Oct. 10: White Sox vs. Cleveland Guardians (Progressive Field, if needed)

Feel the race-day energy of the Chicago Marathon

Cheer on elite athletes and first-time runners during the Bank of America Chicago Marathon on Sunday, Oct. 11.

Each year, the Chicago Marathon draws more than 50,000 runners to the streets of Chicago, attracted by the famously flat and fast course. For spectators, that means a chance to watch world records get shattered.

The 26.2-mile course starts in Grant Park, runs through 29 Chicago neighborhoods, then veers back toward the lakefront for an iconic finish-line celebration.

Check out the best spots to watch the Chicago Marathon, including official cheer zones and neighborhood celebrations.

Cheer on the Chicago Bears

The Chicago Bears are bringing the energy to the lakefront this fall. After last year’s electric season, fans are eagerly anticipating every home game this year.

If you’re heading to Soldier Field, make sure to get there early to tailgate outside the stadium. It’s a longtime tradition for Chicago Bears fans and the perfect way to kick off game day.

When the Bears are away, sports fans can still experience Soldier Field through stadium tours that include the south courtyard, visitors’ locker room and interview room, the skyline suite, colonnades, and the field.

Get tickets to an upcoming home game or cheer on the team at official Chicago Bears bars — though every bar in Chicago feels like a Bears bar on game day.

Chicago Bears home schedule

• Thursday, Oct. 22: Chicago Bears vs. New England Patriots
• Sunday, Nov. 8: Chicago Bears vs. Tampa Bay Buccaneers
• Sunday, Nov. 22: Chicago Bears vs. New Orleans Saints
• Sunday, Dec. 6: Chicago Bears vs. Jacksonville Jaguars
• Friday, Dec. 25: Chicago Bears vs. Green Bay Packers
• Sunday, Jan. 3: Chicago Bears vs. Detroit Lions

See a game at the iconic United Center

The United Center is one of Chicago’s most iconic sports venues, home to two legendary teams: the Chicago Bulls and Chicago Blackhawks.

The Blackhawks kick off their season on Oct. 6 against the rival St. Louis Blues, while the Bulls have their first home game on Oct. 24 against the Washington Wizards.

While you’re there, be sure to snap a photo with the gravity-defying Michael Jordan statue inside the arena’s atrium.

Chicago Bulls home schedule

• Saturday, Oct. 24: Chicago Bulls vs. Washington Wizards
• Wednesday, Oct. 28: Chicago Bulls vs. New York Knicks
• Sunday, Nov. 8: Chicago Bulls vs. Philadelphia 76ers
• Wednesday, Nov. 11: Chicago Bulls vs. San Antonio Spurs
• Friday, Nov. 13: Chicago Bulls vs. Atlanta Hawks
• Friday, Nov. 20: Chicago Bulls vs. Washington Wizards
• Sunday, Nov. 22: Chicago Bulls vs. Denver Nuggets
• Monday, Nov. 23: Chicago Bulls vs. Cleveland Cavaliers
• Saturday, Nov. 28: Chicago Bulls vs. Indiana Pacers

Find more Chicago Bulls home games.

Chicago Blackhawks home schedule

• Tuesday, Oct. 6: Chicago Blackhawks vs. St. Louis Blues
• Saturday, Oct. 10: Chicago Blackhawks vs. Carolina Hurricanes
• Tuesday, Oct. 13: Chicago Blackhawks vs. Pittsburgh Penguins
• Thursday, Oct. 15: Chicago Blackhawks vs. Winnipeg Jets
• Saturday, Oct. 17: Chicago Blackhawks vs. Dallas Stars
• Friday, Oct. 23: Chicago Blackhawks vs. Montreal Canadiens
• Sunday, Oct. 25: Chicago Blackhawks vs. Florida Panthers
• Tuesday, Oct. 27: Chicago Blackhawks vs. Los Angeles Kings
• Monday, Nov. 2: Chicago Blackhawks vs. Colorado Avalanche
• Thursday, Nov. 12: Chicago Blackhawks vs. Buffalo Sabres
• Saturday, Nov. 14: Chicago Blackhawks vs. Winnipeg Jets
• Tuesday, Nov. 17: Chicago Blackhawks vs. Toronto Maple Leafs
• Thursday, Nov. 19: Chicago Blackhawks vs. Columbus Blue Jackets
• Friday, Nov. 27: Chicago Blackhawks vs. New York Rangers
• Sunday, Nov. 29: Chicago Blackhawks vs. Minnesota Wild

Find more Chicago Blackhawks home games.

Catch a soccer match

After the excitement of this summer’s World Cup celebrations, there’s still a bit more soccer to experience this year.

The Chicago Fire play their home games at Soldier Field, joined by legions of loyal fans. Check out the Section 8 Chicago tailgate, then join the official fan march into the stadium before the match.

In Evanston, the Chicago Stars take the field at Martin Stadium on the lakefront Northwestern Campus. Take the CTA Red Line to the Purple Line and catch the last two games of the season.

Chicago Fire home schedule

• Saturday, Oct. 10: Chicago Fire vs. New York City (Anime Day)
• Wednesday, Oct. 14: Chicago Fire vs. Philadelphia (Oktoberfest)
• Wednesday, Oct. 28: Chicago Fire vs. Orlando (Fan Appreciation)
• Saturday, Nov. 7: Chicago Fire vs. Columbus (played at SeatGeek Stadium)

Chicago Stars home schedule

• Sunday, Oct. 18: Chicago Stars vs. Seattle
• Friday, Oct. 23: Chicago Stars vs. Houston

Check out the Chicago Sports Museum

The Chicago Sports Museum is an essential stop for any Chicago sports fan. Located on The Magnificent Mile, this interactive space is filled with game-used items, immersive exhibits, and virtual-reality experiences.

Guests are invited to test their vertical leap against Michael Jordan, try on the largest Super Bowl ring ever made, and see the city’s largest collection of 2016 Cubs World Series memorabilia.

Afterward, grab a bite to eat at Harry Caray’s 7th Inning Stretch, which is covered with photographs from Harry Caray’s private collection and authentic sports memorabilia.

Tour a historic stadium

While the season might be over for the Chicago Cubs, sports fans can still step inside iconic Wrigley Field.

The historic stadium, the second-oldest in the country, offers behind-the-scenes tours all year long. And the off-season is the best time to get a closer look.

Get a close-up look at the seating bowl, bleachers, outfield ivy, press box, visiting clubhouse, dugout, and field. It’s a bucket-list experience for all baseball fans — even if you’re currently rooting for the Sox.

Chicago’s fall events calendar is overflowing with cultural happenings — including music, theatre, film, visual arts, and everything in between.

If you’re looking for things to do this fall in Chicago, mark your calendar for these exciting arts and culture events. From immersive arts experiences to genre-defying film festivals, there’s truly something for everyone to enjoy.

Explore our list of can’t-miss events, grab your tickets, and start looking forward to your jam-packed fall season in the country’s Best Big City.

Art and culture events

Chicago Fashion Week

Oct. 8 – 18, 2026
Back for its third year, Chicago Fashion Week celebrates every aspect of the city’s design ecosystem. Find runway shows, in-store events, pop-up markets, and more.

Arts in the Dark

Oct. 24, 2026
Arts in the Dark celebrates Halloween as the artists’ holiday with a mesmerizing evening parade. Join thousands of spectators in downtown Chicago as they admire the enchanting procession of puppets, giant lanterns, floats, and performers.

312 Comedy Festival

Nov. 5 – 15, 2026
312 Comedy Festival is a multi-day celebration of stand-up comedy that features performances from more than 20 top comedians across six Chicago venues.

Chicago Humanities Festival

Sept. 14 – Nov. 14, 2026
The fall iteration of the Chicago Humanities Festival will include nearly 50 events, featuring luminaries from a range of fields. Hear from famous actors, comedians, photographers, intellectuals, Pulitzer Prize-winning authors, and more.

Theatre and live performances

Jekyll & Hyde at Broadway Playhouse

Sept. 8 – Nov. 8, 2026
Follow the haunting tale of a 19th-century scientist who unknowingly releases an evil alter ego, set to gothic pop-rock tunes in this acclaimed musical production. This production of Jekyll & Hyde follows a completely sold-out and extended-by-demand run in Chicago last year.

Destinos Chicago International Latino Theater Festival

Sept. 14 – Oct. 11, 2026
The 9th annual Destinos International Latino Theater Festival showcases Latino theatre companies from Chicago and across the country. Choose from a variety of works staged at some of the city’s top independent theatre venues.

Kowalski at Lookingglass Theatre Company

Sept. 15 – Oct. 25, 2026
An imaginary meeting between playwright Tennessee Williams and a young Marlon Brando serves as the premise for this fascinating drama. Kowalski, starring award-winning actor Johnny Galecki, will examine the artistry and creative collaboration behind the historic play A Streetcar Named Desire.

Don Giovanni at Lyric Opera

Oct. 10 – Nov. 1, 2026
One of opera’s most famous anti-heroes is brought to life with all the intrigue and deceit that this powerful drama requires. Prepare to be swept up by the intensity and sharp humor of Don Giovanni at the Lyric Opera.

A Christmas Carol

Nov. 12 – Dec. 31, 2026
Between ghostly visits and joyful revelations, A Christmas Carol at the Goodman Theatre channels the holiday spirit with heart and humor. This cherished Chicago tradition brings Charles Dickens’s classic tale to the stage with stunning performances, enchanting sets, and heartfelt moments that capture the season’s true spirit.

Architecture events

Historic Pullman House Tour

Oct. 10 – 11, 2026
Now in its 53rd year, the Historic Pullman House Tour lets guests step inside private homes surrounding Chicago’s landmark Pullman district. Admire historic residential architecture, from workers’ cottages to stately mansions.

Open House Chicago

Oct. 17 – 18, 2026
Open House Chicago is one of the world’s largest architecture festivals. This free citywide event lets you go behind the scenes at hundreds of buildings around Chicago, including skyscrapers, historic landmarks, religious buildings, private clubs, and more.

Film festivals

Chicago International Film Festival

Oct. 14 – 25, 2026
The Chicago International Film Festival is North America’s longest-running competitive film festival. The prestigious event brings 12 days of screenings to venues around the city, plus special events and appearances by directors and talent.

Black Harvest Film Festival

Nov. 6 – 15, 2026
Celebrate Black storytelling in cinema during the 32nd annual Black Harvest Film Festival, spotlighting rising voices and acclaimed filmmakers at the Gene Siskel Film Center.

Museum exhibits

Mary Cassatt: After Impressionism

Sept. 6 – Jan. 3, 2027
The newest exhibit at the acclaimed Art Institute of Chicago, Mary Cassatt: After Impressionism shines a spotlight on the American artist’s most ambitious and experimental work.

Where Memory Lives: 40 Years of Día de Muertos

Sept. 25 – Nov. 29, 2026
The National Museum of Mexican Art hosts this annual exhibition, celebrating the history and culture of Day of the Dead through the perspective of Mexican artists. Where Memory Lives: 40 Years of Día de Muertos traces the evolution of Day of the Dead and the museum itself.

Anne Frank: The Exhibition

Now open through Jan. 31, 2027
Step inside a meticulous full-scale reconstruction of the Annex where Anne Frank and her family hid for two years during Nazi occupation. Anne Frank: The Exhibition at the Griffin Museum of Science & Industry features never-before-seen artifacts from Anne Frank’s life.

Pokémon Fossil Museum

Now open through April 11, 2027
Pokémon Fossil Museum at the Field Museum 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
Explore the experiences of Black artists in Europe as they sought a refuge for creative expression. The Paris in Black collection explores almost a century of Black art at The DuSable Black History Museum and Education Center.

More events to check out

Lincoln Park Wine Fest

Oct. 9 – 11, 2026
Sip wine while strolling an open-air market of sommeliers, food vendors, and live music at Lincoln Park Wine Festival, a local favorite hosted in tranquil Jonquil Park.

Chicago Made Music Showcase

Oct. 24, 2026
Local creatives will perform before a live audience and panel of industry professionals during the Chicago Made Music Showcase Finale at the Chicago Cultural Center for a chance to win a career-changing grand prize.

Explore more: Check out the full list of fall food festivals in Chicago, from tasting events to Oktoberfest celebrations.