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…
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…
After wrapping the final season of Disney Channel’s top-rated show, LIV AND MADDIE, Joey Bragg has been incredibly busy establishing himself as a comedic leading…
Two lifelong friends sail into open water: one edging closer to the pull of oblivion, the other with a question neither can escape. Nobel laureate…
Enjoy a 90-minute improv experience with The Second City, plus two cocktails and small bites for $110. Looking for a unique way to spend your…
After more than a decade of touring nationally, Black Latina (The Play) comes to Chicago for a limited three-day run, October 16–18, 2026. Written by…
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
Ben Schwartz is bringing his “Ben Schwartz & Friends” tour to Chicago for a night of unscripted improv comedy in the fall of 2026.
Catch Your Breath will perform live in Chicago on Saturday, October 17, 2026, as part of their “Not Broken Enough Tour”. Supporting Lineup: This heavy…
Chicago Wolves hockey games are so much fun in person! Check out a Chicago Wolves game this fall at Allstate Arena. The 5-time league champions,…
HERITAGE SERIES is Park Hyatt Chicago’s signature series celebrating the traditions and craftsmanship behind the world’s most celebrated culinary and beverage cultures. The first chapter,…
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…
Saturday Night Sketch brings Chicago’s best sketch comedy ensembles to the stage for a high-octane evening. From sharp political satire to mind melting absurdity, come…
Chicago-based dance company The Seldoms will kick off its 25th anniversary year at Studio5 Performing Arts Center with the world premiere of the new full-length…
Stir Friday Night, Chicago’s premier and longest-running Asian American and Pacific Islander (AAPI) comedy organization, will return to the stage this fall for a two-night…
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,…
Vape! lovingly pokes fun at all of the wonderful moments, sexual innuendos, outrageous characters, rivalries and secret romances from the original musical. The hair products may…
We saw you coming. Fourteen floors above Randolph Street, aerialists fly through a century-old Belgian Spiegeltent while acrobatics, burlesque, cabaret, and comedy unfold around your…
Celebrate 45 years of improvisational excellence with the Best of iO Improv. This show brings together two teams of our very best improvisers, each delivering…
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…
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…
“SANCTUARY STORIES: A JOURNALISM THEATER PROJECT” captures in words and images the lives and communities deeply connected with — and affected by — immigration in…
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:
