Mrs. Doubtfire – The Musical is returning to Chicago for a limited one-week engagement from Tuesday, November 24 through Sunday, November 29, 2026. Directed by…
The Hip Hop Nutcracker will be playing in Chicago from November 24 through November 29, 2026, at the Cadillac Palace Theatre. This contemporary holiday dance…
Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…
One relationship. Infinite possibilities. In how many universes would you love someone? Nick Payne’s Olivier award-winning CONSTELLATIONS is a play about free will and friendship;…
“The Christmas Tree Crawl” is a festive 2-hour “Christmas treasure hunt” walking tour through downtown Chicago, hunting stunning holiday trees and decorations at iconic spots…
A gaggle of suburban moms, armed with pickleball paddles and hard kombucha, are ready to take on the school board in the fight of their…
Oil Lamp Theater is proud to announce the cast and creative team for its next production and the final production in its 2026 season, It’s…
25th anniversary of Chicago’s holiday smash hit! Filled with heartwarming storytelling, music, and some very special surprises. George Bailey – the Everyman from small town…
“The Christmas Tree Crawl” is a festive 2-hour “Christmas treasure hunt” walking tour through downtown Chicago, hunting stunning holiday trees and decorations at iconic spots…
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…
ZooLights Presented by Invesco and ComEd returns to Lincoln Park Zoo, lighting up the city’s favorite holiday tradition once again! Over 3 million lights and…
Chicago-based conceptual artist Stephanie Brooks and Washington-based still life and landscape painter David Kroll are exhibiting their works at the Zolla / Lieberman Gallery in…
Chicago’s Drive Through Light Show located at White Sox, Rate Field opens November 19, 2026. Make holiday memories from your warm car!
Whitechapel is performing live in Chicago on Saturday, November 28, 2026, at The Riviera Theatre as part of their massive 20th Anniversary Tour. Lineup: Whitechapel,…
The Kids Show For Adults. It’s the all-ages magic show that’s actually fun for all ages. This is not a sweet, gentle, clap-along children’s show.…
Main Character Syndrome is a solo character showcase by Chicago’s funniest improvisers presenting original SNL-audition ready character sketches. From Tim Robinson to Cecily Strong, iO…
Intuit Art Museum (IAM), recognized worldwide as one of the few institutions dedicated solely to championing the work of self-taught artists, marks the 250th anniversary…
Feast on a fantastic dinner, but just beware… the killer is hiding somewhere in the room, and you may find yourself as a Prime Suspect.…
The Second City’s 114th Mainstage Revue Pandemonium, Please Hold is a loud, fast, and gloriously unhinged night of comedic mayhem. The Second City’s six-person cast…
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Millennials take on Generation X in a live stand-up comedy battle – and the audience decides who wins. Hosted by Chicago comedian Todd Glover, Standup…
21+ ONLY Brianna Wellen, Chicago Reader: Sideshow entertainer Thom Britton’s solo show is part performance, part demonstration. Britton is a charismatic performer who appears genuinely…
Reality Detox: The Improv Experience is a high-energy night of improvisation from The Second City, with a few sketch surprises mixed in along the way. Built…
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…
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…
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…
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…
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…
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…
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…
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’s event calendar reflects the city itself — bold, diverse, and always buzzing. From lakefront music festivals and neighborhood street fairs to major sporting events and food celebrations, there’s something happening in every season.
Here’s a look at the types of events you’ll find across the city:
Other Chicago events include cultural celebrations, sporting events, conventions, comedy shows, live theatre, and so much more.
Chicago’s biggest annual events draw visitors from around the world and highlight the very best of the city’s food, music, and culture.
These signature events help define Chicago as one of the top festival cities in the country.
If you’re planning a trip around Chicago’s event calendar, there’s something new to discover every month of the year.
Summer is peak festival season. The city comes alive with outdoor concerts, neighborhood street fests, and major events like Lollapalooza, Taste of Chicago, and the Chicago Air and Water Show. Nearly every weekend offers something new, especially along the lakefront and in Millennium Park.
Early fall brings cooler temperatures and marquee events like the Chicago Marathon and culinary celebrations such as Chicago Gourmet. It’s an ideal time for visitors seeking cultural events like the Chicago International Film Festival.
Winter brings a dose of holiday magic to Chicago, with beloved traditions like ZooLights and Christkindlmarket. Visitors can also check out cultural celebrations for the Lunar New Year and enjoy local-favorite annual events like Chicago Restaurant Week and Chicago Theatre Week.
Spring is the perfect time to visit Chicago for culture lovers. Check out spring flower shows, top art fairs like EXPO Chicago, and bucket-list traditions like Chicago’s St. Patrick’s Day celebrations. It’s also the start of outdoor events, with baseball season kicking off in late March.
Chicago is known for offering an impressive lineup of free events, particularly in the summer months.
Some of the city’s most popular free events include:
Come experience the unmatched energy of Chicago’s legendary sports scene, from our fan-favorite teams to our historic stadiums and iconic events.
Catch a game by one of Chicago’s major league teams:
Other major annual sporting events in Chicago include:
