Searching for what to do this week in Chicago? Below are the best things to do in Chicago this week (April 27-May 3, 2026) including the best events and activities.
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Best Events This Week in Chicago
Below are the best events this week in Chicago:
Chicago Jazz Club Experience – Monday, April 27, 2026, 5:50-10:30pm
Chicago Latino Film Festival – Through April 27, 2026
Edgar Allan Poe Speakeasy – April 30-May 2, 2026
Mexico Fest at Navy Pier – May 1-3, 2026 | Free
Chicago Market for Makers at Artifact Events – May 2 + 3, 2026
May Market at the Driehaus Museum – Saturday, May 2, 2026, 11am-5pm | Free – Shop vintage jewelry, local artisans, and other goods from 20+ local vendors. The Driehaus Museum Store will be selling special spring merchandise, and there will be an activity table for younger visitors and a photo op.
Ravenswood Makers Market @ KOVAL – Saturday, May 2, 2026, 1-6pm
Cinco De Mayo Weekend Booze Cruise – Saturday, May 2, 2026, 3pm
Saturday Night at the Zoo – An Adults Only Evening at Lincoln Park Zoo – Saturday, May 2, 2026, 6:30-10pm
Chicago Artisan Market (Fulton Market) – Sunday, May 3, 2026, 11am-5pm
Chicago Children’s Museum Kids Free Day – Sunday, May 3, 2026, 10am-5pm
The Volunteer Fair – Sunday, May 3, 2026, 12-4pm | Free
Another Vegan Market at Emporium Logan Square – Sunday, May 3, 2026, 12-4pm | Free
Doc10 Film Festival – Through May 3, 2026
Chicago Critics Film Festival at Music Box Theatre – May 1-7, 2026 – Chicago’s only film festival curated by critics.
More Events in Chicago This Week
Below are more events taking place this week in Chicago:
The Jazz for Chicago Big Band Celebrates UNESCO World Jazz Day at the Chicago Cultural Center – Monday, April 27, 2026, 12-1:30pm | Free
After5Society – Becoming You: The Psychology Behind Who You Are – Monday, April 27, 2026, 6:30-8:30pm
Shedd Aquarium Illinois Resident Free Night – Tuesday, April 28, 2026, 5-9pm
Faith, Fissures & the Future: Former Vice President Mike Pence in Conversation at the University of Chicago’s Institute of Politics – Tuesday, April 28, 2026, 5:30-6:45pm
An evening of Jazz at the Paris in Black exhibit at the DuSable Black History Museum & Education Center – Tuesday, April 28, 2026, 5:30-7:30pm | Free
The International Jazz Day: Live the Spirit at Hamilton Park – Tuesday, April 28, 2026, 5:30-7:30pm | Free
Chicago to the World: A Jazz Celebration at Garfield Park Conservatory – Tuesday, April 28, 2026, 6-7:30pm | Free (pre-registration required)
Sex and the City Trivia Night – Tuesday, April 28, 2026, 7-8:30pm
International Jazz Day at Epiphany Center for the Arts – Tuesday, April 28, 2026, 7:30-9:30pm
Illinois Free Wednesdays at the Field Museum – Wednesday, April 29, 2026
Adler Planetarium Free Day (Illinois Resident Discount Day) – Wednesday, April 29, 2026
Illinois Holocaust Museum presents Experience 360 Free Day – Wednesday, April 29, 2026
Pay What You Wish Wednesday at Driehaus Museum – Wednesday, April 29, 2026, 4-7pm
Bruce Springsteen and The E Street Band Land Of Hope And Dreams American Tour – Wednesday, April 29, 2026, 7:30pm
Schtick @ Schubas Free Comedy Showcase – Wednesday, April 29, 2026, 8-10pm | Free
Chicago History Museum Free Admission Day for Illinois Residents – Thursday, April 30, 2026
Valborg (Andersonville) – Thursday, April 30, 2026, 5-8pm
Thrift Lab at Griffin Museum of Science and Industry – Thursday, April 30, 2026, 6–10pm – Grab a cocktail or mocktail and explore the intersection of fashion and sustainability. Browse their pop-up thrifting marketplace, featuring more than 15 eclectic and size-inclusive vendors. Learn the basics of sewing, mending, embellishments or buttoning at the Lillstreet Art Center’s mending hub and contribute to a communal fashion project.
Jazz Occurrence, Celebrating International Jazz Day Live at Fulton Street Collective – Thursday, April 30, 2026, 6-10pm | Free
Summer House Trivia Night – Thursday, April 30, 2026, 7-9pm
Adults Night at the Trampoline Park (21+ Only) – Thursday, April 30, 2026, 7:30-8:30pm
Demi Lovato: It’s Not That Deep Tour at the United Center – Friday, May 1, 2026, 8pm
EVOLUTION: Asian American Arts Festival – May 2-3, 2026
Ritmo de Mayo at Logan Square Auditorium – Saturday, May 2, 2026, 8pm
The Jury Experience: Death on the Port Side – Sunday, May 3, 2026, 3pm & 5:30pm
The Jazz Room: A Tribute to Frank Sinatra & Louis Armstrong – Sunday, May 3, 2026, 4pm & 6pm
You can find more Chicago weekend events here.
Anne Frank The Exhibition at the Griffin Museum of Science and Industry – Opens May 1, 2026
The Great Gatsby at Cadillac Palace Theatre – Through May 3, 2026
The Merry Wives of Windsor at Chicago Shakespeare Theater on Navy Pier – Through May 3, 2026 – The secret lives of Windsor wives reveal more than just dirty laundry in an endlessly entertaining new take on Shakespeare’s most raucous comedy.
Ma Rainey’s Black Bottom at Goodman Theatre – Extended through May 3, 2026
More Things to Do in Chicago This Week
Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place next weekend include:
Tribute to The Beatles
Tribute to Bad Bunny (Oak Park)
Tribute to Coldplay on Strings (Oak Park)
You can find the full list of candlelight concerts in Chicago here.
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
See the Spring Flower Show at the Garfield Park Conservatory
Enjoy the annual Spring Flower Show exhibit at the Garfield Park Conservatory.
Where: 300 N. Central Park Ave., Chicago, IL 60624
Cost: $10 for adults; $5 for seniors (65+), college students and kids (7-17). Admission is FREE for Chicago residents with proof of residency as well as all children under age 7.
See the Spring Flower Show at the Lincoln Park Conservatory
The Lincoln Park Conservatory also has an annual Spring Flower Show.
Where: 2391 N. Stockton Drive, Chicago, IL 60614
Cost: Free.
Watch a Drunk Shakespeare Play
Join The Drunk Shakespeare Society for an unforgettable evening of Shakespearean revelry. Set within a speakeasy, five actors attempt to perform a Shakespearean play after one of them downs multiple shots of various alcohols. Every show is different depending on who is drinking and what they’re drinking. Must be 21+ with valid ID.
Where: The Lounge At The Lion, 182 North Wabash Avenue
Cost: Prices start at $29 per person. Click here to purchase tickets.
Wondra: Immerse yourself in the magic of nature
Looking for a fun activity for kids? Head to the suburbs for Wondra, where each space invites curious minds to discover hidden details, dazzling colors, and natural awe-scapes that spark imagination and evoke wonder. Experience nature’s wonders in a whole new light with this immersive journey.
Where: 5 Woodfield Mall, Schaumburg, IL 60173
Cost: Prices vary. Click here to see prices and purchase tickets in advance.
As you can see there are many things to do in #Chicago this week. If you are looking for more things to do in the Chicago area, you can find the best things to do in the suburbs here. If you are planning ahead, you can find more things to do in Chicago in April and Chicago in May.
