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…
Improvised Jane Austen Improvised Jane Austen continues its entirely improvised tales of love and laughter. Audiences will enjoy an evening with wit and heart in…
Rediscover the soundtrack of a lifetime with GOING BACHARACH, a vibrant new revue, direct from a sold-out run in New York, celebrating the legacy of…
16-time Grammy winner Bruno Mars /w special guests Leon Thomas & DJ Pee.Wee will perform live at Chicago’s Soldier Field on May 16-17, 2026.
Ari Lennox is bringing The Vacancy Tour to Chicago for a performance at The Chicago Theatre on Saturday, May 16, 2026.
It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…
Shhhhh! It’s a secret! Don’t tell anyone but your favorite iO performers are hosting a wild night of variety and sketch. Secret sketch show is…
IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street,…
Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…
The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…
A mature Diva, I’m M$ B’Havin is built on a young woman’s frame; however, is not your typical Mama! She’ll give you the Blues, with…
Muse is a unique cabaret and burlesque experience with a focus on live music. The musings continue with 2026’s Chicago Cabaret Week! Join Boobs Radley,…
Since when do irreverence and genuine warmth go together? Since “Quirky”! Come hear a mix of offbeat, funny, honest and uplifting songs about love, longing…
Jack Grady is a comedy magician whose chaotic, unpredictable style has earned him a cult following and millions of fans across the internet. One of…
Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…
Julio Torres is scheduled to perform in Chicago on Sunday, May 17, 2026, for his “Works in Progress” show.
Toronto indie rock band Good Kid /w special guest Inoha will perform live at Chicago’s Riviera Theatre on May 17, 2026.
16-time Grammy winner Bruno Mars /w special guests Leon Thomas & DJ Pee.Wee will perform live at Chicago’s Soldier Field on May 16-17, 2026.
It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…
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…
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring…
The Chaos and Carnage 2026 tour will be at the Ramova Theatre in Chicago on Tuesday, May 19, 2026. This year’s installment features a massive…
Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…
Joe Jackson and his band are scheduled for a two-night residency at Park West in Chicago on Tuesday, May 19, and Wednesday, May 20, 2026.…
The historic, tree-lined streets of Chicago’s storied Hyde Park neighborhood are filled with Gothic architecture, cultural landmarks, and a welcoming energy that gives it a…
May is a jam-packed month in Chicago — summer is on the horizon, tulips are blooming all over the city, and weekends fill up with…
AAPI Heritage Month Events in Chicago This May, Chicago will celebrate the city’s diverse AAPI communities. Here are a few ways to participate: Admire never-before-seen…
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…
In 1871, the Great Chicago Fire swept through the city and destroyed much of downtown. Yet Chicago rose from the ashes, building back bigger and…
Summer in Chicago just wouldn’t feel complete without the city’s beloved street festivals, which include an eclectic array of neighborhood celebrations across the city. These…
If you’ve never been to a cabaret show, Chicago is a great place to start. With a 100-plus year history rooted in the city’s early…
Chicago’s summer event calendar is overflowing with cultural happenings. From groundbreaking art exhibits to exciting theatrical premieres, there’s truly something for everyone to enjoy. Check…
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:
