From picking the perfect pumpkin, toasting s’mores over a fire pit, to rides and entertainers, this free festival offers something new and different each weekend…
Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…
It’s the best comedy show in the city. Created in 1995 by iO alum Armando Diaz, Armando is a historic improvisational form where actors improvise a series…
All the cool kids stay out late on a school night! Join new teams as they deliver a short and sweet show filled with laughter…
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
Join Adam Selzer—author, podcaster, and host of Mysterious Chicago Tours—for spine-tingling walkabouts that dig into the zoo’s cemetery roots and locations from throughout its allegedly…
“Take thuh cards and show me whatcha got!” Brothers Lincoln and Booth, named in jest, are two Black men living in America just trying to…
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
“Take thuh cards and show me whatcha got!” Brothers Lincoln and Booth, named in jest, are two Black men living in America just trying to…
A weekly improv show hosted by Blue.0 and featuring a rotating cast of indie teams formed right here at The iO Theater! Each Wednesday at…
Join Adam Selzer—author, podcaster, and host of Mysterious Chicago Tours—for spine-tingling walkabouts that dig into the zoo’s cemetery roots and locations from throughout its allegedly…
A showcase of 3 short plays by select writing teams and featuring a cast of iO Theater performers. It’s experimental, it’s follow-the-fun, it’s Play Time. Plays…
The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…
Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…
Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
With the help of some of Chicago’s best actors, Improv: The Play is a new, hybrid version of long form improv happening only at the…
If you’re looking for a date night, girls’ night out, or a mandatory work outing (that your staff will actually like) — Look no further!…
World Premiere dystopian fable written by Broadway’s Eric Coble. ‘The Fix’ was supposed to correct everything that had gone wrong with the country. Now, three…
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…
Tin Drum Theatre Company announces the Chicago premiere of A Dark Wood, October 15 – November 1, written by Eric Coble and directed by Steve…
Nominated “Best Comedy Show” by the Chicago Reader (2025), Sketch Playlist is a weekly sketch show that will feature all-new sketches every single week… the…
Blueprint is the kind of improv that keeps audiences AND players on their toes. Each week, a different cast member designs a bold new improv format…
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
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…
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…
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…
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…
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:
