Searching for what to do this week in Chicago? Below are the best things to do in Chicago this week (May 11-17, 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:
Asian American Showcase – Through May 12, 2026
Wrigleyville Night Market at Gallagher Way – Thursday, May 14, 2026, 4-8pm | Free
Mayfest – May 15-17, 2026
Crosstown Classic series – Chicago Cubs vs White Sox at Rate Field – May 15-17, 2026
Spring Lincoln Roscoe Art & Craft Fair – May 16-17, 2026
Renegade Craft Fair – May 16-17, 2026
Hyde Park Garden Fair – May 16-17, 2026 – Chicago’s oldest community garden sale.
Howard Street Carnaval – Saturday, May 16, 2026 | Free
Manifest: Kaleidoscope – Saturday, May 16, 2026, 9am-10pm | Free – Celebrate the 25th Anniversary of Manifest, an arts festival featuring the creativity and accomplishments of Columbia College’s graduating students.
Malört Crawl – Saturday, May 16, 2026, 12-5pm
Spring Fun Fest at Parkway Bank Park (Rosemont) – Saturday, May 16, 2026, 1-5pm | Free – Free outdoor event featuring family-friendly activities including bounce houses, balloon sculptors, face painters, a petting zoo and live entertainment.
Chicago Humanities Spring Festival Northwestern University Day – Sunday, May 17, 2026
Portage Park Chalk Art Festival – Sunday, May 17, 2026, 11am-2pm | Free – The inaugural Chalk Art Festival offering a community-focused event with sidewalk decorating, food vendors, live music and kids activities. Participants can reserve a sidewalk square to create art, for a chance to win local prizes.
Edison Park Sip and Stroll Wine Walk – Sunday, May 17, 2026, 2-6pm
Andersonville Spring Wine Walk – Sunday, May 17, 2026, 3-6pm
Budweiser Concert Series: Mayday Parade at Gallagher Way – Sunday, May 17, 2026, 6-9pm
Chicago Cabaret Week – Through May 17, 2026
More Events in Chicago This Week
Below are more events taking place this week in Chicago:
Pilates with Rise Pilates Club at Gallagher Way – Monday, May 11, 2026, 7-8am | Free – First class of the year.
Strengthening Our Democracy at the Chicago Cultural Center – Monday, May 11, 2026, 12-3pm
Swing Dancing at Gallagher Way – Monday, May 11, 2026, 7-10pm | Free – First dance class of the season.
Shedd Aquarium Illinois Resident Free Night – Tuesday, May 12, 2026, 5-9pm
Get Lit: Art of the Cocktail at the American Writers Museum – Tuesday, May 12, 2026, 5:30-7:30pm
Chicago Queer Wedding Show – Tuesday, May 12, 2026, 6-9pm
HIIT at Gallagher Way – Wednesday, May 13, 2026, 7-8am | Free
Illinois Free Wednesdays at the Field Museum – Wednesday, May 13, 2026
Adler Planetarium Free Day (Illinois Resident Discount Day) – Wednesday, May 13, 2026
Open Pond Paddle at Thatcher Glen Pond (River Forest) – Wednesday, May 13, 2026, 2-6pm | Free
Pay What You Wish Wednesday at Driehaus Museum – Wednesday, May 13, 2026, 4-7pm
West Town Clean Up and Drinks – Wednesday, May 13, 2026, 6-7:30pm | Free
Outdoor Movie: How to Train Your Dragon (Live Action) at Gallagher Way – Wednesday, May 13, 2026, 6-10pm | Free
Feel Good Bunny Yoga at Cuddle Bunny – Wednesday, May 13, 2026, 7:15-8:15pm
Morning All-Levels Yoga Class at Gallagher Way – Thursday, May 14, 2026, 7-8am | Free
Skate Night Market w/ Johnny Walker at Emporium Logan Square – Thursday, May 14, 2026, 8pm-midnight | Free
Hubbard Street Spring Series at the Harris Theater for Music and Dance – May 14-15 & 17, 2026
Bruno Mars The Romantic Tour at Soldier Field – May 16 & 17, 2026
Broadway on Adams – May 14–16, 2026 – A festive evening, cabaret style at 625 W. Adams featuring songs from Broadway performed by the Old St. Patrick’s Music Ministry.
Play From The Upper Deck Inside Wrigley Field – May 14-16, 2026
Anime Central – May 15-17, 2026
Tropical Cocktail Fest on the Beach – Cocktail Tasting at North Ave. Beach – Friday, May 15, 2026, 6pm
Bad Bunny Dance Night – Friday, May 15, 2026, 9pm
Millennium Park Free Summer Workout – Saturday, May 16, 2026, 8-11:45am | Free
Wright Plus Architectural Housewalk (Oak Park) – Saturday, May 16, 2026
Trash Bash at LaBagh Woods – Saturday, May 16, 2026, 9am-12pm | Free – Recycle electronics, prescription drugs, household recyclables, bikes, clothing, plastic bags and more.
Family Day: Games on the Go at Smart Museum of Art – Saturday, May 16, 2026, 11am-2pm | Free
Summer Kickoff Day Party at Shore Club – Saturday, May 16, 2026, 11am-2pm
Planting Seeds: An Indigenous Zine Fest at the Newberry Library – Saturday, May 16, 2026, 11am–3pm
Asian American Heritage Month at Caldwell Wellness Center – Saturday, May 16, 2026, 2pm-3pm
Free Day at the American Writers Museum – Sunday, May 17, 2026 | Free
David Sedaris at the Auditorium Theatre – Sunday, May 17, 2026, 2pm
Civic Orchestra Fellows & New Music – Sunday, May 17, 2026, 7pm | Free (reservations required)
Maxwell Street Market Opening Date – Sunday, May 17, 2026, 10am–3pm | Free Admission – Monthly market on Maxwell Street between S. Halsted St. and S. Union Ave featuring foods and goods including handmade crafts, resale housewares and clothing.
Ravenswood Manor Garage Sale – Sunday, May 17, 2026, 10am-4pm – One of the largest, community-wide, garage sales in Chicago.
You can find more Chicago weekend events here.
Les Misérables at Cadillac Palace Theatre – May 12-24, 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
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:
Back in Black
Rings and Dragons
Tribute to The Beatles
Tribute to Bad Bunny (Oak Park)
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.
Where: The Fields Studios – Gate 1, 2828 N. Pulaski, Chicago, IL 60641
Cost: Timed-entry tickets are required. Click here to purchase tickets.
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
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.
