One of the most provocative and enduring theatrical works to emerge from the AIDS crisis. The play follows J.R. and Bert, two gay men who…
Revisiting characters established in August Wilson’s SEVEN GUITARS, this play returns to Pittsburgh’s Hill District in 1985. King Hedley, a man recently released from prison,…
Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…
Award-winning Redtwist Theatre’s new 22nd season, “State of Violence,” begins with Prayer Circle, September 17 – November 8, by Erik Gernand and directed by Executive…
Originally commissioned for Goblincon in Hopkinsville, Kentucky, “Kentucky’s Friendliest Cryptids” follows Agents Hill and Montgomery on their quest to prove the existence of cryptids. And…
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…
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…
Widely discussed performer James Tom will bring his “Goes on a Mini-Tour, Casual Style” show to Chicago on Sunday, November 1, 2026.
A strange object in the sky. A cursed gas station hot dog. A llama with government clearance. Our performers create a brand new story influenced…
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…
Joel James is anationally touring stand-up comedian, social media entertainer, and self-published cookbook author. Known for his viral comedic skits, high-energy stage presence, and sharp…
Experience the official “Outlander” in-concert event! A live orchestra performs Bear McCreary’s acclaimed score, curated by showrunner Matthew B. Roberts, while highlights from eight seasons…
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…
Bad Gyal will perform at the Riviera Theatre in Chicago on Sunday, November 1, 2026, as part of her “Más Cara World Tour”.
L7 is bringing “The Last Hurrah Tour 2026” to The Vic Theatre on Sunday, November 1, 2026.
The dream pop and synthwave duo New Constellations is scheduled to perform live in Chicago on Sunday, November 1, 2026, at 7:30 PM. They will…
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…
Rod Wave is scheduled to perform live in Chicago, Illinois on Sunday, November 1, 2026, as part of his newly announced Don’t Look Down Tour.…
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…
On July 4, 2026, America turned 250 years old. To reckon with the 250th anniversary of the Declaration of Independence is to reckon with freedom…
PlayGround-Chicago presents Season 5 MONDAY NIGHT PLAYGROUND November 2, 2026, 7pm CT NEW VENUE: The Den & Simulcast Topic: AMERICA 250: The Dreamers, The Builders &…
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…
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:
