The 10th Anniversary tour of the hit Broadway musical Waitress is coming to the James M. Nederlander Theatre in Chicago, Il, October 17-18, 2026. The…
Tin Drum Theatre Company announces the Chicago premiere of A Dark Wood, October 15 – November 1, written by Eric Coble and directed by Steve…
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…
“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…
THE SWALLOW is set during a private singing lesson between a choral director and a new student. As they work together on a song, what initially…
Oil Lamp Theater is proud to announce the cast and creative team for its next production, Dial M for Murder, October 2 – November 1,…
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…
Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…
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.…
Clarketoberfest at the Harley Clarke Mansion Oct. 16–18 brings three days of FREE fall fun, beer, food by Hatchet Burger, dancing, family festivities, and live…
Curious Theatre Branch, with co-producers Chicago Danztheater Ensemble, Chicago Dramatists and Labyrinth Club, are pleased to announce the 37th annual Rhinoceros Theater Festival, September 20…
“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…
Step into a world where light and dance intertwine in this breathtaking retelling of Sleeping Beauty. As dancers glide across the stage, their illuminated costumes…
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…
The creator of 420 Shakespeare is bringing Mary Shelley’s monster to life… with a little help from Mary Jane. On a dark and stormy night,…
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.…
Cheer on the Chicago Blackhawks at the United Center!
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…
Rising pop/country singer-songwriter Knox (Knox Morris) will perform live in Chicago on Saturday, October 17, 2026, at the House of Blues Chicago. The concert is…
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…
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:
