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 over the city this month in Chicago.
This weekend brings a ton of exciting happenings, including Chicago’s International Jazz Day celebrations. Find concerts, exhibits, tours, and more that explore the city’s rich jazz legacy.
Check out just a few of the events and happening in Chicago this weekend, May 1 – 3, 2026.
International Jazz Day 2026 All-Star Global Concert
With artistic direction by Herbie Hancock and Kurt Elling, this blockbuster concert is the centerpiece of International Jazz Day 2026 in Chicago and will feature a record number of acclaimed artists from around the world.
Mexico Fest at Navy Pier
Head to Navy Pier for a free celebration of Mexican culture, bringing together music and dance performances, workshops, and over 30 vendors showcasing their offerings in a mercadito shopping experience.
Trading Card Con
FOR IMMEDIATE RELEASE THE CARDS & MORE EXPO BRINGS TRADING CARD CON TO CHICAGO May 1st-3rd, 2026 Chicago, IL— The nationwide Cards & More Tour’s…
Wicker Park Bucktown’s “First Fridays” Art Walk
Wicker Park Bucktown Chamber of Commerce welcomes art enthusiasts to the next upcoming “First Fridays Art Walk.” Participants will have the opportunity to explore the…
An Evening With South Chicago Dance Theatre
South Chicago Dance Theatre presents its ninth annual home season concert and return to the Harris Theater For Music and Dance on May 1, 2026!…
ABLEfest – celebrating 10 years of Artists Breaking Limits & Expectations
Join A.B.L.E. - Artists Breaking Limits &Expectations as we celebrate our 10th anniversary of creating theatre and film for, with, and by individuals with intellectual…
135th Annual Polish Constitution Day Parade
Chicago’s Polish Constitution Day Parade is the city’s oldest continuously running parade and the largest Polish parade in the world held outside of Poland. It…
Chicago Fireboat Tours Busse Birthday Bash
Celebrate aboard the historic Fred A. Busse, a 1936 fireboat preserved as a floating museum and flagship of Chicago Fireboat Tours. This dockside spring party…
Isaiah Collier: In Tribute to the Classics of John Coltrane
Isaiah Collier’s saxophone sound is both fierce and deeply reflective—rooted in tradition yet stretching toward the future. Named Chicago Tribune’s Jazz Artist of the Year and…
You Win Some, You Dim Sum: an uplifting comedy show
We don’t celebrate our wins enough — so we made a comedy show where you can watch stand-up, win dim sum treats, and celebrate each…
The Head and The Heart at Auditorium Theatre
Alternative music reigns over North America this 2026 because The Head And The Heart just plotted the North American dates and will be touring many…
Spring Flower Show: Showers of Flowers
Join us this spring for Showers of Flowers, the 2026 spring flower show at the Garfield Park Conservatory. “Showers of Flowers” highlights more than 80 hanging baskets that demonstrate vertical possibilities for your green thumb! The baskets will feature trailing vines, like ivy and sweet potato, bushy asparagus ferns, and colorful flowers like pansies, petunia, and calibrachoa.
Theater of the Mind
Now through July 12, 2026 Multiple experiences per day at the Reid Murdoch Building, 333 N LaSalle Visit TheateroftheMindChicago.com for dates, times, and tickets Created…
Matisse’s Jazz: Rhythms in Color
This exhibition marks the first time Matisse’s Jazz will be shown in its entirety at the Art Institute of Chicago. Jazz joins over 50 works from the museum’s renowned collection of paintings, sculpture, drawings, prints, illustrated books, and textiles.
The Great Gatsby
THE PARTY’S ROARING IN CHICAGO! THE GREAT GATSBY is a “Broadway extravaganza that explodes with life and energy” (Entertainment Weekly). Based on the classic American novel…
Doc10 Film Festival
Doc10 is Chicago’s only all-documentary film festival and provides an engaging experience for its audiences, reaching thousands of local cinephiles over the last nine years.…
Yes, Chef! Chicago: A Bear-Inspired Food Tour
This is the ORIGINAL Chicago food tour that takes you to the restaurants featured on the TV phenomenon, The Bear. We'll take you to the actual…
Dovetail Brewery Tour
Take a tour of one of the most unusual breweries in the U.S.
Our tours explore the traditional European brewing methods that define Dovetail—from open fermentation and horizontal lagering to our coolship and a 100-year-old copper kettle. Along the way, you’ll taste beer, handle raw ingredients, and finally learn exactly what the heck a coolship is.
The Merry Wives of Windsor
Delight in Shakespeare’s most raucous comedy! The secret lives of Windsor wives reveal there is much more to this charming, middle-class English hamlet than meets…
The Dover Road
Welcome to the home of the eccentric Latimer, who waylays couples who are running away together and gives them a taste of what their lives…
Glow Wild
Starting March 19, experience Glow Wild: A Lantern Festival of Hope — a breathtaking journey of light, art, and conservation. Wander paths under the moonlight, illuminated by…
American Prophets: Writers, Religion, and Culture
American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…
Balloon Museum: EmotionAir
The Pop Air and Let’s Fly exhibitions continue to thrill and engage a participative audience, but EmotionAir sets an even more ambitious goal. This latest…
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
