Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (May 22-25, 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:
Belmont-Sheffield Music Festival – May 22-24, 2026
Forever Mine Music Festival (new) – May 23-24, 2026
Warm Love Cool Dreams Music & Arts Festival at the Salt Shed – May 23-24, 2026
Sueños Music Festival – May 23-24, 2026
Mayfestiversary – May 23-24, 2026 – Begyle Brewing and Dovetail Brewery are hosting their annual spring party.
Randolph Street Market – May 23+24, 2026, 10am-5pm
Live on the Lake! at Navy Pier – May 22-25, 2026 | Free
Summer Kickoff at Lincoln Park Zoo – May 22-25, 2026 | Free
Ravenswood Spring Vintage & Artisan Fest presented by Windy City Market – May 23-24, 2026, 12-5pm
Pokémon Fossil Museum at the Field Museum – Opens May 22, 2026
AirOtic Soirée – Opens May 22, 2026
Adults Night Out: Block Party at Lincoln Park Zoo (21+) – Friday, May 22, 2026, 6:30-10pm
Memorial Day Wreath Laying Ceremony and Parade – Saturday, May 23, 2026, 11am
Summer Fireworks at Navy Pier – Saturday, May 23, 2026, 10pm | Free – First fireworks show for the summer season.
Black Boy Art Show at Navy Pier – Sunday, May 24, 2026, 3-9pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Morning Dance Cardio and Sculpt Class at Gallagher Way – Friday, May 22, 2026, 7-8am | Free
Chi Food Truck Fest – Friday, May 22, 2026, 11am-3pm
Solomun at Union Park – Friday, May 22, 2026, 4pm
The Walking Body at the International Museum of Surgical Science – Friday, May 22, 2026, 7-9pm
Soldier Field 10 Memorial Day Run – Saturday, May 23, 2026
Millennium Park Free Summer Workout – Saturday, May 23, 2026, 8-11:45am | Free
Wellness in the Woods: Yoga at Dan Ryan Woods – Saturday, May 23, 2026, 11am-12pm | Free
Germ Party! at International Museum of Surgical Science – Saturday, May 23, 2026, 12-1pm – Teach kids about the importance of washing hands and maintaining healthy hygiene with glow-in-the-dark fun.
Memorial Day Weekend Kickback – Saturday, May 23, 2026, 2-6pm
Studio Sale at Arts of Life – May 21-24, 2026
Les Misérables at Cadillac Palace Theatre – Through May 24, 2026
Fault at Chicago Shakespeare Theater on Navy Pier – Through May 24, 2026 – Dark comedy directed by Jason Alexander and starring Enrico Colantoni and Teri Hatcher.
Spamalot at CIBC Theatre – May 19-31, 2026
Legendary Late Hours at the Field Museum – May 23-26, 2026, 5-9pm
Chicago History Museum Free Admission Day for Illinois Residents – Monday, May 25, 2026
Beverly/Morgan Park Ridge Run & Memorial Day Parade – Monday, May 25, 2026, 8am
McKinley Park’s Memorial Day Parade – Monday, May 25, 2026, 10am
Norwood Park Memorial Day Parade – Monday, May 25, 2026, 11am-12:30pm
Cornhole Competition + Heroes for Heroes Give Back Program at Lottie’s Pub – Monday, May 25, 2026, 12-3pm
Secret River Show – Monday, May 25, 2026, noon-7pm | Free
Self-Defense Class at Gallagher Way – Monday, May 25, 2026, 7-8pm | Free
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:
Join a Memorial Day Party Cruise
Join these Memorial Day themed booze cruises throughout the weekend and party on a boat with music and a festive atmosphere:
“The Lake House” Memorial Weekend Yacht Party
Memorial Day Fireworks Booze Cruise
Memorial Day Weekend Cruise | All White Attire Party
Memorial Day Party Cruise
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:
90s Unplugged
Tribute to Fleetwood Mac
The Best of Hans Zimmer
You can find the full list of candlelight concerts in Chicago here.
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.
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.
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 May here.
