Searching for what to do next weekend? Below are the top things to do in Chicago next weekend (May 22-25, 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:
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
Oddball Market at The Salt Shed – May 23-24, 2026
Legendary Late Hours at the Field Museum – May 23-26, 2026, 5-9pm
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.
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
Chicago History Museum Free Admission Day for Illinois Residents – Monday, May 25, 2026
More Next Weekend Events in Chicago
Below are more weekend events taking place next 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
PAWS Chicago Adoption Event at Gallagher Way – Saturday, May 23, 2026, 7-8am | Free
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 your 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
Les Misérables at Cadillac Palace Theatre – Through May 24, 2026
Fault at Chicago Shakespeare Theater on Navy Pier – Through May 24, 2026 – Starring Enrico Colantoni and Teri Hatcher, this dark comedy directed by Jason Alexander is full of blistering humor and searing revelations.
Self-Defense Class at Gallagher Way – Monday, May 25, 2026, 7-8pm | Free
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:
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 – Friday, May 22, 2026, 8-11:30pm
Memorial Day Fireworks Booze Cruise – Saturday, May 23, 2026, 8-11:30pm
Memorial Day Weekend Cruise | All White Attire Party – Sunday, May 24, 2026, 9pm-midnight
Memorial Day Party Cruise – Monday, May 25, 2026, 8:30-11pm
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.
Where: 9900 Berwyn Ave, in the Pearl District, Rosemont, IL 60018
Cost: Prices vary. Click here to purchase tickets.
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 next weekend include:
Tribute to Fleetwood Mac
90s Unplugged
The Best of Hans Zimmer
You can find the full list of candlelight concerts in Chicago here.
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.
