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…
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…
Legendary Trinidadian soprano Jeanine De Bique has taken Europe by storm in recent years. In this stunning new program designed by Jeannette Sorrell, De Bique…
The School of the Art Institute of Chicago Fall Undergraduate Exhibition showcases the culminating work of graduating seniors. This exhibition features the ambitious and innovative…
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…
November 8 & 12 | DREAMS IN NIGHTMARES follows three estranged childhood friends who embark on an impromptu road trip across America, transforming a journey…
Design Graveyard is a free, two-week exhibition of design work that never made it out of the studio. It collects abandoned concepts, rejected pitches, unbuilt…
Musical theatre and improv collide as Marquee presents you with an hour of fully improvised musical comedy, spontaneously creating entire scenes, songs, and stories based…
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…
November 7 & 8 | EVERYDAY PEOPLE considers community as a living practice, sustained through shared histories, spiritual traditions, cultural expression, political struggle, and everyday…
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…
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…
Ron White is performing live in Chicago on Sunday, November 8, 2026, at The Chicago Theatre. His performance is presented by the 312 Comedy Festival.
Acclaimed folk-pop singer-songwriter Joy Oladokun will perform live in Chicago on Sunday, November 8, 2026, at 7:00 PM. This highly anticipated performance is part of…
In 1981, iO Theater started a revolution that shaped modern comedy and launched the sharpest, funniest voices in the industry. Join us November 5-7 as…
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…
See the show that started it all, and experience the iO Theater’s groundbreaking, signature improv form: The Harold! This long-running, weekly improv tradition is double-headlined…
After four years of sold-out performances, Port of Entry returns for its final season beginning Oct. 29. Created by Albany Park Theater Project and Third…
Vince Staples will perform live in Chicago on Sunday, November 8, 2026, at the Riviera Theatre. The concert is part of his newly announced Cry…
Chicago’s longest-running Harold team returns to iO to bring their unique blend of chaos and creativity to iO’s signature form The Harold melding games, songs, and scenes…
90s alternative rock mainstays Better Than Ezra are bringing their signature high-energy show to Chicago, Illinois, on November 8, 2026, performing at House Of Blues.
Join Comedian Barry Brewer for a fun night of stand up comedy with a mix of crowd collaboration and conversation. Barry Brewer hails as one…
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…
Chicago’s cultural scene doesn’t slow down when the temperature drops. Winter in Chicago is packed with tons of exciting happenings, including blockbuster museum exhibits, hit…
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…
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…
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…
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:
