Searching for what to do this week in Chicago? Below are the best things to do in Chicago this week (May 25-31, 2026) including the best events and activities.
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.
Best Events This Week in Chicago
Below are the best events this week in Chicago:
Centennial Wheel 10th Anniversary at Navy Pier – Wednesday, May 27, 2026 – 10th Anniversary celebration of the Centennial Wheel with special offers and deals across the Pier, including $10 Centennial Wheel tickets all day.
World Otter Day at the Wild Mile – Wednesday, May 27, 2026, 6-9pm | Free
Do Division Street Fest (West Town) – May 29-31, 2026 | Free (suggested $10 donation) – Live music, local vendors, food, fashion shows and family-friendly programming on Division Street between Damen and Leavitt.
Maifest (Lincoln Square) – May 29-31, 2026 | Free – Traditional German celebration at Lincoln Ave. & Western.
Windy City Hot Dog Fest – May 29-31, 2026
Magnificent Mile™ Art Festival – May 30-31, 2026
Arte Agave Tequila and Mezcal Festival – Friday, May 29, 2026, 6-9:30pm
BARK (Lincoln Park) – Saturday, May 30, 2026, 8am-12pm – 2-mile dog-friendly charity walk ending in a party in the park.
Chicago Dance Month Kickoff Celebration – Saturday, May 30, 2026, 3-5pm | Free
Kite Festival at Douglass Park – Saturday, May 30, 2026, 12-4pm | Free
Lakeview Porchfest – Sunday, May 31, 2026, 1-5pm – Local musical acts performing across front porches throughout Lakeview. Enjoy an intimate live music experience while connecting with neighbors and supporting local musicians.
More Events in Chicago This Week
Below are more events taking place this week in Chicago:
Yoga Class at Gallagher Way – Tuesday, May 26, 2026, 7-8am | Free
Legendary Late Hours at the Field Museum – Tuesday, May 26, 2026, 5-9pm
Shedd Aquarium Illinois Resident Free Night – Tuesday, May 26, 2026, 5-9pm
Policing & Public Trust Town Hall at Thalia Hill – Tuesday, May 26, 2026, 6-7:15pm
Big Cheese Poetry Slam at Zhou B Art Center (Bridgeport) – Tuesday, May 26, 2026, 6:30-9pm
Wellness in the Sky- Sound Bath Meditation at Skydeck Chicago – Tuesday, May 26, 2026, 6:30-9pm
HIIT at Gallagher Way – Wednesday, May 27, 2026, 7-8am | Free
Illinois Holocaust Museum presents Experience 360 Free Day – Wednesday, May 27, 2026
Illinois Free Wednesdays at the Field Museum – Wednesday, May 27, 2026
Adler Planetarium Free Day (Illinois Resident Discount Day) – Wednesday, May 27, 2026
Pay What You Wish Wednesday at Driehaus Museum – Wednesday, May 27, 2026, 4-7pm
Jazzin’ at the Shedd – Starts Wednesday, May 27, 2026, 5-10pm
May in Motion: Circuit Training at Tom (Ping) Memorial Park – Wednesday, May 27, 2026, 2026, 6-7pm | Free
The Karate Kid at Gallagher Way – Wednesday, May 27, 2026, 6-10pm | Free
Bunnies, Books & Chill at Cuddle Bunny – Wednesday, May 27, 2026, 6:30-8pm
Free Yoga in LaPointe Park (Ravenswood) – Wednesday, May 27, 2026, 6:30-7:30pm
Iconic Movie Moms Trivia at Replay Andersonville – Wednesday, May 27, 2026, 7-9pm | Free
Schtick @ Schubas Free Comedy Showcase – Wednesday, May 27, 2026, 8-10pm | Free
Summer Fireworks at Navy Pier – Wednesday, May 27, 2026, 9pm | Free
Yoga Class at Gallagher Way – Thursday, May 28, 2026, 7-8am | Free
Wrigleyville Night Market at Gallagher Way – Thursday, May 28, 2026, 4-8pm | Free
Skyline Session at Navy Pier – Starts Thursday, May 28, 2026, 5-9pm | Free – Free live music from talented solo artists and small ensembles every Thursday and Friday through September 4, 2026
Adults Night at Altitude Trampoline Park – Thursday, May 28, 2026, 7:30-8:30pm
Belle and Sebastian at Salt Shed (Indoor Shed) – Thursday, May 28, 2026, 8pm
Wine Fest on the Beach – Wine Tasting at North Ave. Beach – Friday, May 29, 2026, 6pm
47th Ward Eco Fest – Saturday, May 30, 2026, 10am–2pm
Wrigleyville Taco Crawl – Saturday, May 30, 2026, 11am-6pm
Repair Fair at Chicago Tool Library (Garfield Park) – Saturday, May 30, 2026, 1-3:30pm | Free
House Music is Home at Navy Pier – Saturday, May 30, 2026, 4:30-9:30pm | Free with RSVP
Bobby Lee at the Chicago Theatre – Saturday, May 30, 2026, 7pm
Night Nation Run – Saturday, May 30, 2026, 8:30pm
Summer Fireworks at Navy Pier – Saturday, May 30, 2026, 10pm | Free
SummerSalt Market at The Salt Shed Outdoors (Fairgrounds) – Sunday, May 31, 2026, 11am-5pm | Free
National Tap Dance Day Celebration at DuSable Black History Museum – Sunday, May 31, 2026, 5pm
You can find more Chicago weekend events here.
Cunning Folk Theatre Presents Stories at Athenaeum Center (Lakeview) – May 27–31, 2026
Brokeback Mountain at Chicago Shakespeare Theater – May 28 – June 28, 2026
Monty Python Spamalot at CIBC Theatre – Through May 31, 2026
Windfall at Steppenwolf Theatre – Through May 31, 2026
Sapphopalooza Film Series at Music Box Theatre – Through May 31, 2026
Matisse’s Jazz: Rhythms in Color Exhibition at the Art Institute of Chicago – Through June 1, 2026
More Things to Do in Chicago This Week
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 week include:
A Tribute to Taylor Swift
Tribute to Drake
Best of Bridgerton on Strings
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: Through July 5, 2026
Where: 9900 Berwyn Ave, in the Pearl District, Rosemont, IL 60018
Cost: Prices vary. Click here to purchase tickets.
AirOtic Soirée
AirOtic Soirée is a bold, sensual and provocative cabaret-circus experience returning to Chicago for a full summer run. After sold-out runs across the U.S. and Europe, the internationally acclaimed Airotic Soirée is a show that celebrates desire, sensuality, athletic beauty, and erotic elegance. Airotic Soirée is a blend of erotic cabaret and contemporary circus blending high-level acrobatics, seductive choreography and visual artistry. 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.
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.
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.
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 week. 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 planning ahead, you can find more things to do in Chicago in May.
