Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (August 21-23, 2026) including the best events and activities.
{If you are planning ahead, you can also find the best things to do next weekend here.)
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Best Weekend Events in Chicago
Below are the best weekend events in Chicago:
Lakeview Taco Fest – August 21-23, 2026 | Free ($10 suggested donation)
West Loop Art Fest – August 22-23, 2026, 10am-7pm | Free
Bulls Fest – August 22-23, 2026
Thirsty Ears – August 22-23, 2026 | Free ($10 suggested donation) – Chicago’s only classical music street festival.
Evanston Art & Big Fork Festival – August 22-23, 2026 | Free
Serial Killer Speakeasy – August 20-22, 2026
The Dramatic Improv Festival – August 20-23, 2026
Anime Magic – August 21-23, 2026
Supertri Chicago (formerly the Chicago Triathlon) – August 22-23, 2026 – North America’s largest triathlon with beginner-friendly programs, relay racing and a Corporate Challenge benefiting Ann & Robert H. Lurie Children’s Hospital of Chicago.
Adults Night Out: Crafted at Lincoln Park Zoo (21+) – Friday, August 21, 2026, 6:30–10pm
Candlelight Concert: Queen vs. ABBA – Friday, August 21, 2026, 6:30pm
Candlelight Concert: Tribute to Metallica – Friday, August 21, 2026, 8:45pm
South Asian American Lit Fest – Saturday, August 22, 2026, 10am | Free
Wrigleyville Country Fest – Saturday, August 22, 2026, 11am-6pm
Chalk Howard Street – Saturday, August 22, 2026, 11am-7pm | Free Admission – Chicago’s only 3D chalk art festival invites national and local street artists, neighbors, families, and street art lovers to transform Howard Street in Rogers Park into a creative canvas.
Villapalooza – Saturday, August 22, 2026, 12-10pm | Free
Summer Wine Down at Gallagher Way – Saturday, August 22, 2026, 1-7pm
Summer Whiskey Tasting Festival – Saturday, August 22, 2026, 2:30-6pm
Zoo Uncorked at Brookfield Zoo (21+) – Saturday, August 22, 2026, 4-8pm
The Lawndale Route 66 Festival – Sunday, August 23, 2026, 10am-7pm | Free
Galewoodstock Music Festival – Saturday, August 22, 2026, noon-9pm
Cluck ’N Bubble – Sunday, August 23, 2026, 12-4pm – Inaugural fried chicken & Champagne event.
Sunday in the Park with Lyric – Sunday, August 23, 2026, 7pm | Free
Queens of Soul: Aretha to Beyonce Under the Stars at AIRE Rooftop – Sunday, August 23, 2026, 5pm & 8pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Dance Cardio and Sculpt at Gallagher Way – Friday, August 21, 2026, 7-8am | Free
Chi Food Truck Fest – Friday, August 21, 2026, 11am-3pm
Bronzeville Art District Trolley Tour – Friday, August 21, 2026, 6pm | Free
Third Friday Art Walk @ Zhou B Art Center – Friday, August 21, 2026, 7pm | Free
Bridgeport Third Friday Art Walk – Friday, August 21, 2026, 7-10pm | Free
Billy Currington at The Salt Shed Outdoors – Friday, August 21, 2026, 6pm
Kacey Musgraves Middle of Nowhere Tour at United Center – Friday, August 21, 2026, 7:30pm
Millennium Park Free Summer Workout – Saturday, August 22, 2026, 8-11:45am | Free Admission
ACS Kids Zone (at Navy Pier) – Saturday, August 22, 2026, 11am-2pm | Free (but registration is encouraged)
Art On Clark (Lincoln Park) – Saturday, August 22, 2026, 11am–3pm | Free – See live sidewalk chalk drawings created by Chicago artists.
Many Voices, One Heart at Ping Tom Park – Saturday, August 22, 2026, 2-4pm | Free – Family-friendly musical presentation uniting Asian performing arts organizations for a vibrant evening of cross-cultural musical exchange.
Lake Stage Summer Concert Series: Noche Caribeña (at Navy Pier) – Saturday, August 22, 2026, 6-8:45pm | Free
Par-Tee at Gallagher Way – Sunday, August 23, 2026, 10am-1pm | Free – Golf activities for families.
Andersonville Vintage Market – Sunday, August 23, 2026, 11am-5pm – Outdoor event at Ashland & Catalpa featuring a curated mix of vintage clothing, home goods, vinyl, furniture and handmade treasures.
Community Day: IAM a garden at Intuit Art Museum – Sunday, August 23, 2026, 11am-6pm | Free – A free admission day at Intuit Art Museum with all-ages activities.
Vintage House Outdoor Lakeview Market – Sunday, August 23, 2026, 12-5pm
GWCN Chicago: Wild Mile Walk – Sunday, August 23, 2026, 1-2pm | Free
Light Up The Lanes: An All-Ages Skee-Ball™️ Tournament – Sunday, August 23, 2026, 1-4pm | Free
Bottomless Margaritas on the Riverwalk (Ages 21+) – Sunday, August 23, 2026, 3-5pm
Dine Out On Broadway – August 21-23, 2026
Bottomless Mimosas on the Riverwalk (Ages 21+) – August 22 & 23, 2026, 11am-1pm
Hell in a Handbag Productions Presents Joan Crawford Goes To Hell at The Clutch – August 21 – September 27, 2026
SAW The Musical: The Unauthorized Parody of SAW – Through September 6, 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.
Take a Lake Cruise
Enjoy a cool lake breeze and admire the Chicago skyline from a lake cruise.
If your time is short, you can do a combination river and lake cruise.
Watch Fireworks
Watch fireworks at Navy Pier every Saturday at 10pm in the summer. The fireworks can be seen from various spots along the Lakefront including North Avenue Beach, Oak Street Beach and the Adler Planetarium Skyline Walk.
The best and most relaxing way to see the Navy Pier fireworks show is on a fireworks lake or river cruise.
If you enjoy guided tours, you can also see the fireworks and other attractions on this fireworks segway tour.
Kayak in the River or Lake
A fun way to explore the city is to go kayaking in the Chicago River or Lake Michigan. You can rent a kayak in the Chicago River here and Ohio Street Beach here.
You can also join a guided kayaking tour in the downtown portion of the Chicago River including this history and architecture kayak tour and this sunset kayak tour.
Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
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 Queen
A Tribute to Drake
Tribute to the Beatles (Oak Park)
You can find the full list of candlelight concerts in Chicago here.
Titanic: A Voyage Through Time
Step into history at Titanic: A Voyage Through Time an extraordinary virtual reality (VR) journey into history’s most famous ship. Dive to the wreckage as it rests today, then travel back to 1912 to experience the Titanic as a passenger. Walk the Grand Staircase, meet the people who shaped its story, and witness history firsthand in this immersive adventure.
When: Through September 27, 2026
Where: 108 West Germania Place, Chicago, IL 60610
Cost: Prices vary. Click here to purchase tickets.
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.
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: Through 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.
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 August here.
