Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (June 5-7, 2026) including the best events and activities.
{If you are planning ahead, you can also find the best things to do next weekend here.)
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.
Best Weekend Events in Chicago
Below are the best weekend events in Chicago:
Chicago Blues Festival – June 4-7, 2026 | Free Admission – The largest free Blues festival in the world.
Ribfest Chicago – June 5-7, 2026
Lincoln Park Greek Fest – June 5-7, 2026
Pokémon GO Fest – June 5–7, 2026
57th Street Art Fair – June 6-7, 2026 | Free
Beyond Wonderland (at Huntington Bank Pavilion at Northerly Island) – June 6-7, 2026
American Writers Festival – June 6 & 7, 2026, 10am-5pm | Free
Chicago Vintage Festival (Bridgeport) – June 6 & 7, 2026, 12-6pm | Free Entry
Lincoln Park Health & Wellness Weekend – June 6-7, 2026
Chicago Oddities & Curiosities Expo – June 6-7, 2026
Rosemont Uncorked – June 6-7, 2026
Uptown Art Walk – Saturday, June 6, 2026, 10am-4pm | Free
Festival Del Niño – Saturday, June 6, 2026, 11am-3pm | Free
The Great Bake Walk – Sunday, June 7, 2026, 10am-1pm – Explore Lincoln Square and Ravenswood while sampling delicious baked goods from a variety of local bakeries.
High Vibes Festival – Sunday, June 7, 2026, 2-8:30pm
Sinatra Under The Stars at AIRE Rooftop – Sunday, June 7, 2026, 5pm & 8pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Rise Pilates Club Summer Series at Oak Street Beach – Friday, June 5, 2026, 6-8am | Free
Chi Food Truck Fest – Friday, June 5, 2026, 11am-3pm
Jazz In the Court (Hyde Park) – Friday, June 5, 2026, noon-2:30pm | Free
Griffin Museum of Science and Industry Kickoff to Summer Picnic (Outdoors) – Friday, June 5, 2026, 11am-3pm | Free
Wicker Park Bucktown First Fridays Art Walk – Friday, June 5, 2026, 6-8pm | Free – Monthly free self-guided monthly art walk throughout Wicker Park and Bucktown visiting galleries, local artist pop-ups, artist talks and more.
First Friday Music Series (Rogers Park) – Friday, June 5, 2026, 6-8pm – Evening of live music on Sheridan Rd. between Devon and Pratt.
Horner Park Famers Market Opening Day – Saturday, June 7, 2026, 9am-1pm
Roscoe Village Community Garage Sale – Saturday, June 6, 2026, 9am-3pm
North Mayfair Garage Sale – Saturday, June 6, 2026, 9am-3pm
Edgewater Yard and Sidewalk Sale – Saturday, June 6, 2026, 9am-5pm
Club Capri: Rooftop Party Series at Castaway’s Beach Club – Saturday, June 7, 2026, 9am-11pm
Ravenswood Front Yard FreeCycle – Saturday, June 6, 2026, 9am-3pm – It’s like a yard sale, but everything is free.
Ravenswood Sidewalk Sale – Saturday, June 6, 2026, 10am-5pm
Lake Stage Summer Concert Series at Navy Pier – Saturday, June 6, 2026, 6-8:45pm | Free
Summer Fireworks at Navy Pier – Saturday, June 6, 2026, 10pm | Free
BWild x Wicker Park Farmers Market (WPFM) Free Summer Outdoor Yoga Series – Sunday, June 7, 2026, 9-10am | Free
Bad Bunny Hot Pilates at Cuddle Bunny – Sunday, June 7, 2026, 9-10am
Glenwood Sunday Market Opening Day – Sunday, June 7, 2026, 9am-2pm
Barre3 in the Park (Mary Bartelme Park) – Sunday, June 7, 2026, 9:30-10:30am | Free
Sunrise Yoga On 31st St. Beach – Sunday, June 7, 2026, 10-11am
Maxwell Street Market – Sunday, June 7, 2026, 10am–3pm | Free Admission
Art of Pride at Hyde Park Art Center – Sunday, June 7, 2026, 12-4pm | Free
Southport Summer Jam – Sunday, June 7, 2026, 2–4pm | Free – Family-friendly party at the corner of Southport and Henderson hosted by the Boka Restaurant Group with complimentary bites & sips, giveaways, face painters, activities for kids and more.
The Jazz Room: A Journey to the Heart of New Orleans – Sunday, June 7, 2026, 4pm & 6pm
Eugene Onegin at Lyric Opera House – June 4—14, 2026
Brokeback Mountain at Chicago Shakespeare Theater – Through June 28, 2026
Catch As Catch Can at Steppenwolf Theatre – June 4–July 12, 2026
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:
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
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:
Tribute to Rush
Best of Bridgerton on Strings
You can find the full list of candlelight concerts in Chicago here. (Tickets are up to 20% off from 6/4-6/7/26)
Minecraft Experience: Villager Rescue
Minecraft Experience: Villager Rescue is an immersive adventure that lets you and your friends become heroes, fighting spiders, creepers, and skeletons on your quest to rescue villagers from a zombie attack. Explore eight interactive Minecraft rooms and gather resources for your quest in these interactive biomes. Practice your Minecrafting skills with a handheld Orb to chop down trees, collect resources, and fight mobs.
When: May 9 – July 5, 2026
Where: 9900 Berwyn Ave, in the Pearl District, Rosemont, IL 60018
Cost: Prices vary. Click here to purchase tickets. (Tickets are 20% off from 6/4-6/7/26)
AirOtic Soirée
AirOtic Soirée is a bold, sensual and provocative cabaret-circus experience blending high-level acrobatics, seductive choreography and visual artistry. After sold-out runs across the U.S. and Europe, it is returning to Chicago for a full summer run. 21+ with valid ID.
When: May 22-August 29, 2026
Where: Experience 868, 868 North Franklin Street, Chicago, IL 60610
Cost: Prices vary. Click here to purchase tickets. (Tickets are 20% off from 6/4-6/7/26)
Balloon Museum’s EmotionAir Exhibition
Balloon Museum’s EmotionAir Exhibition is a limited time unique exhibition that explores the profound relationship between art and emotions through the captivating medium of inflatable art. This exhibition, first presented in London in December 2023, is committed to the work of emotions, transforming artworks into mirrors to explore the profound relationship between art and emotions, action, and reaction. This is manifested tangibly through Inflatable Art, which offers itself as a medium to express the most intimate nuances of human feelings. Through a mix of interactive installations, emotional projections, and performance art, EmotionAir aims to transport visitors on an unprecedented sensory journey.
When: Extended through September 7, 2026
Where: The Fields Studios – Gate 1, 2828 N. Pulaski, Chicago, IL 60641
Cost: Timed-entry tickets are required. Click here to purchase tickets.
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. (Tickets are 25% off from 6/4-6/7/26)
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 this week here and the best things to do in Chicago in June here.
