Searching for what to do this week in Chicago? Below are the best things to do in Chicago this week (August 17-23, 2026) including the best events and activities.
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Best Events This Week in Chicago
Below are the best events this week in Chicago:
Crosstown Classic series at Wrigley Field – August 17-19, 2026
Serial Killer Speakeasy – August 20-22, 2026
The Dramatic Improv Festival – August 20-23, 2026
Lakeview Taco Fest – August 21-23, 2026
Anime Magic – August 21-23, 2026
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
Supertri Chicago (formerly the Chicago Triathlon) – August 22-23, 2026
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
Galewoodstock Music Festival – Saturday, August 22, 2026, noon-9pm
The Lawndale Route 66 Festival – Sunday, August 23, 2026, 10am-7pm | Free
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 Events in Chicago This Week
Below are more events taking place this week in Chicago:
Pilates at Gallagher Way – Monday, August 17, 2026, 7-8am | Free
Kicking It Curbside (Pilsen) – Monday, August 17, 2026, 7-9pm | Free – Live music and drink specials every Monday in the summer on Allport Street.
Yoga Class at Gallagher Way – Tuesday, August 18, 2026, 7-8am | Free
Tuesdays on the Terrace – Tuesday, August 18, 2026, 5:30–8pm | Free, but tickets are limited
Pier Fitness – Tuesday, August 18, 2026, 6-8:30pm | Free
Millennium Park Summer Film Series: Sinners – Tuesday, August 18, 2026, 6:30pm (gates open at 5pm) | Free Admission – Final movie of the season.
HIIT at Gallagher Way – Wednesday, August 19, 2026, 7-8am | Free
Illinois Free Wednesdays at the Field Museum – Wednesday, August 26, 2026
Jazzin’ at the Shedd – Wednesday, August 26, 2026, 5-10pm
After5Chicago – The Relationship Blueprint: The Psychology of Manipulation – Wednesday, August 19, 2026, 6:30-8:30pm
Bottomless Margaritas on the Riverwalk (Ages 21+) – Wednesday, August 19, 2026, 6:30-9pm
CatJam Chicago Jam Session at The Wild Mile – Wednesday, August 19, 2026, 7-10pm | Free
Summer Fireworks at Navy Pier – Wednesday, August 19, 2026, 9pm | Free
Yoga Class at Gallagher Way – Thursday, August 20, 2026, 7-8am | Free
Wrigleyville Night Market at Gallagher Way – Thursday, August 20, 2026, 4-8pm | Free
Art Institute of Chicago Free Hours for Illinois Residents – Thursday, August 20, 2026, 5–8pm | Free
Third Thursdays
On Grand Avenue – Thursday, August 20, 2026, 5-8pm – Neighborhood-wide summer celebration in West Town as local businesses stay open late for an evening of special offerings.
Argyle Night Market – Thursday, August 20, 2026, 5-9pm | Free
Mending & Margaritas at Chicago Fair Trade Museum & Store – Thursday, August 20, 2026, 5:30-8pm
Wild Mile Projections: Skunk Run – Gųųšgoonąk – Thursday, August 20, 2026, 9-9:30pm | Free
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
Art On Clark (Lincoln Park) – Saturday, August 22, 2026, 11am–3pm | Free – See live sidewalk chalk drawings created by Chicago artists.
Lake Stage Summer Concert Series: Noche Caribeña (at Navy Pier) – Saturday, August 22, 2026, 6-8:45pm | Free
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
You can find more Chicago weekend events here.
Summerdance: Spirit of Music Garden in Grant Park – August 20-22, 2025, 6-9pm | Free
Dine Out On Broadway – August 21-23, 2026
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
Sunday in the Park with George – Through November 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.
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 Wednesday at 9pm and 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 week 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 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: Through August 29, 2026
Where: Experience 868, 868 North Franklin Street, Chicago, IL 60610
Cost: Prices vary. 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 August.
