Searching for what to do next weekend? Below are the top things to do in Chicago next weekend (May 1-3, 2026) including the best events and activities.
(You can find the best things to do this weekend here.)
I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.
Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.
Next Weekend Events in Chicago
Below are the best next weekend events in Chicago:
Edgar Allan Poe Speakeasy – April 30-May 2, 2026
Mexico Fest at Navy Pier – May 1-3, 2026 | Free
Doc10 Film Festival – April 24 – May 3, 2026
Anne Frank The Exhibition at the Griffin Museum of Science and Industry – Opens May 1, 2026
Chicago Critics Film Festival at Music Box Theatre – May 1-7, 2026 – Chicago’s only film festival curated by critics.
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
More Next Weekend Events in Chicago
Below are more weekend events taking place next weekend in Chicago:
Demi Lovato: It’s Not That Deep Tour at the United Center – Friday, May 1, 2026, 8pm
Fiber+Fabric Craft Festival (Rosemont) – May 1-3, 2026 | Free
The International Gem & Jewelry Show (Rosemont) – May 1-3, 2026
EVOLUTION: Asian American Arts Festival – May 2-3, 2026
Gala de Arte: Agua Sagrada – Friday, May 1, 2026, 6-11pm
Isaiah Collier: ‘In Tribute to the Classics of John Coltrane’ at Logan Center for the Arts – Friday, May 1, 2026, 7:30pm
Mike Reed’s Chicago Inspirations at Symphony Center – Friday, May 1, 2026, 8pm
AANHPI Heritage Month Trivia Walk at Dan Ryan Woods – Saturday, May 2, 2026, 10am-1pm | Free
Margarita Madness Bar Olympics – Saturday, May 2, 2026, 11:30am-4pm
Wander Home Holiday Market – Mother’s Day Edition – Saturday, May 2, 2026, 12-6pm | Free
I|O Godfrey Kentucky Derby Viewing Event – Saturday, May 2, 2026, 12-8pm
The Tunes-N-Tequila “TNT” Cinco De Mayo Crawl – Saturday, May 2, 2026, 2-10pm
Derby at the Depot – Saturday, May 2, 2026, 3-7pm
Cinco De Mayo Bar Crawl – Saturday, May 2, 2026, 4pm-1am
Chicago Cinco De Mayo Bar Crawl – Saturday, May 2, 2026, 5-11pm
Ritmo de Mayo at Logan Square Auditorium – Saturday, May 2, 2026, 8pm
Lakefront Loop 5K at Navy Pier – Sunday, May 3, 2026, 8am
Jefferson Park Winter Market – Sunday, May 3, 2026, 10am-2pm – Last indoor market of the year.
Puzzle Exchange at Jefferson Park – Sunday, May 3, 2026, 12-3pm | Free
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
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.
Matisse’s Jazz: Rhythms in Color Exhibition at the Art Institute of Chicago – Through June 1, 2026
More Things to Do in Chicago Next Weekend
In addition to the weekend events listed above, below are more of the best things to do in Chicago next weekend:
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.
Take a Spray Paint ‘n’ Sip Urban Art Workshop
Grab some spray paint and unleash your inner street artist at a Spray Paint ‘n’ Sip Urban Art Workshop. This interactive spray paint workshop will teach you the ins and outs of working with spray paint and other elements of graffiti and street art as you create your own painted mural.
Where: Studio W.I.P. – Uptown, 1047 W Lawrence Ave, Chicago, IL 60640
Cost: $45 per person for adults. 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 next weekend. If you are looking for things to do during the week, here are more things to do in Chicago in May.
