Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (May 2-4, 2025) including the best weekend events and activities.
(If you are planning ahead, you can also find the best things to do next weekend here.)
I suggest bookmarking this blog post as it is updated 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.
Best Weekend Events in Chicago
Below are the best weekend events in Chicago:
Mexico Fest at Navy Pier – May 2-4, 2025 | FREE
Doc10 Film Festival – Through May 4, 2025
Chicago Critics Film Festival at Music Box Theatre – May 2-8, 2025 – Chicago’s only film festival curated by critics.
First Friday Music Series (Rogers Park) – Friday, May 2, 2025, 6-8pm – Evening of live music on Sheridan Rd. between Devon and Pratt.
Friday Night Concert: Gabriel Datcu at St. James Lutheran Church & School – Friday, May 2, 2025, 7-8pm | FREE
Cinco De Mayo Celebration at Calumet Park – Friday, May 2, 2025, 7-8pm | FREE – Family-oriented celebration of Cinco De Mayo featuring a live Mariachi band.
The Tunes-N-Tequila “TNT” Cinco De Mayo Crawl – Saturday, May 3, 2025, 2-10pm
May Music On The Wild Mile! – Saturday, May 3, 2025, 1-8pm | FREE – Celebrate spring on the Wild Mile with live music by local musicians, yoga, and more.
Cinco De Mayo Booze Cruise – Saturday, May 3, 2025, 3-6pm
Dining in the Dark: A Unique Blindfolded Experience at About Last Knife – Saturday, May 3, 2025, 6:00 & 8:30pm
Puzzle Exchange at Jefferson Park – Sunday, May 4, 2025, 12-3pm | FREE
Edison Park Sip and Stroll Wine Walk – Sunday, May 4, 2025, 2-6pm
Spring Wine Walk (Andersonville) – Sunday, May 4, 2025, 3-6pm
Trinity Irish Dancers at the Irish-American Heritage Center – Sunday, May 4, 2025, 5-7pm | FREE
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Sensory Feast: A Magical Dining Experience – May 2 & 3, 2025, 6pm & 8:30pm
Midway Spring Bar Crawl – Friday, May 2, 2025, 6–10pm
Gala de Arte: Orgullo Mexicano – Friday, May 2, 2025, 6-11pm -The National Museum of Mexican Art’s annual benefit at the Hyatt Regency Chicago.
Zoo-ologie (21+) – Friday, May 2, 2025, 5:30–10 pm
Wicker Park Bucktown First Fridays Art Walk – Friday, May 2, 2025, 6-8pm | FREE – Monthly, free art walk throughout the neighborhoods of Wicker Park and Bucktown visiting galleries, local artist pop-ups, artist talks and more.
Bottomless Mimosas on the Riverwalk (Ages 21+) – Saturday, May 3, 2025, 11am-1pm
Polish Constitution Day Parade – Saturday, May 3, 2025, 11:30am – On Columbus Dr. from Balbo St. to Monroe St.
Chicago Pickle Fest: Live Bands, Beer and Everything Pickle (Ages 21+) – Saturday, May 3, 2025, 11am
Chicago Chamoy Fest – Flamin’ Hot, Pica, & Everything In-Between (Ages 21+) – Saturday, May 3, 2025, 1pm
The Newport Peekeasy: Burlesque and Variety Show – Saturday, May 3, 2025, 7:00–8:30pm – See a combination of burlesque, belly dance, drag and other live dance performances in a speakeasy vibe.
Lakefront Loop 5K at Navy Pier – Sunday, May 4, 2025, 8am – All proceeds benefit Navy Pier’s nonprofit mission.
St. Jude Police Memorial March – Sunday, May 4, 2025, 8am – Museum Campus Dr. from Solidarity Dr. to Waldron
Wicker Park Farmers Market – Sunday, May 4, 2025, 8am-2pm – First day of the 25th season of the Wicker Park Farmers Market.
Jefferson Park Winter Market – Sunday, May 4, 2025, 10am-2pm
You Win Some, You Dim Sum – Sunday, May 4, 2025, 5-7pm – Comedy show where audiences share their wins of the week, eat some good Dim Sum, and build a community that uplifts each other.
French Macaron class – Sunday, May 4, 2025, 6pm
The Jury Experience: An Immersive Courtroom Case – Sunday, May 4, 2025, 6pm & 8:30pm
More Things to Do in Chicago This Weekend
In addition to the weekend events listed above, below are more of the best things to do in Chicago this 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 this weekend include:
Candlelight: Tribute to Adele – Friday, May 2, 2025, 7pm & 9:15pm
Candlelight: The Best of Hans Zimmer – Saturday, May 3, 2025, 4:30pm
Candlelight: A Tribute to Queen and More – Saturday, May 3, 2025, 6:30pm & 8:45pm
Candlelight Concert: A Tribute to ABBA – Saturday, May 3, 2025, 6:30pm
You can find the full list of candlelight concerts in Chicago here.
The Empire Strips Back: A Burlesque Parody at The Studebaker Theater
The Empire Strips Back: A Burlesque Parody at The Studebaker Theater is a limited time burlesque parody show which drops classic Star Wars characters into the world of burlesque with a unique blend of seduction and sci-fi.
When: Through May 4, 2025
Where: The Studebaker Theater, 410 South Michigan Avenue Fine Arts Building, Chicago, 60605, IL 60642
Cost: Prices start at $54 per person. Click here for full prices and to purchase tickets in advance.
See Beautiful Tulips In and Around Chicago
Tulip season is here! There are several places in Chicago and the suburbs where you can admire these beautiful spring flowers.
Every year thousands of tulip bulbs are planted in Michigan Avenue medians from Oak Street to Roosevelt Road. Although not as many as tulips as Michigan Avenue, you can also find some tulips on State Street in the Loop between W Wacker Drive and Monroe – including right across the Chicago Theatre.
You can see beautiful outdoor tulip gardens at various parks and gardens in the suburbs including Cantigny Park in Wheaton and the Chicago Botanic Garden in Glencoe.
You can also walk in and take photos in large tulips fields at Richardson Adventure Farm in Spring Grove, Illinois and Kuipers Family Farm in Maple Park, Illinois.
Read Best Places to See Tulips in and near Chicago for more places to see tulips in and near Chicago.
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
Look for Street Art
See Chicago’s many murals by joining a street art tour.
Spring Flower Show at the Garfield Park Conservatory
Check out the annual Spring Flower Show, “Rooted in Mystery” at the Garfield Park Conservatory, which explores the different types of roots and the cool stuff they do plus a marvelous display of spring plants, including azaleas, pansies, snapdragons, astilbe, baptisia, hydrangeas, and 26 different varieties of tulips, daffodils, and hyacinths.
Spring Flower Show at the Lincoln Park Conservatory
The free Lincoln Park Conservatory also as its annual Spring Flower Show, “Spectrum of Spring”, which highlights the color families of plants and flowers and offers a unique design and color scheme.
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.
As you can see there are many things to do in Chicago this weekend. 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 looking for things to do during the week, you can find more things to do in Chicago in May here.
