Want to know what’s happening this weekend in Chicago? Look no further. There’s a whole calendar of exciting events, exhibits, and activities taking place all over the city this month in Chicago.
Highlights this weekend include:
- Cheer on athletes as they run, bike, and swim in Lake Michigan during the Supertri Chicago.
- Enjoy neighborhood festivals like the Lakeview Taco Fest, West Loop Arts Festival, and more.
- Check out classic cars, music, local food, and more at the Route 66 Festival in Lawndale, celebrating 100 years of the iconic route.
Check out just a few of the events and happening in Chicago this weekend, Aug. 21 – 23.
The Lawndale Route 66 Festival
The Lawndale Route 66 Festival is a vibrant community celebration held on historic Ogden Avenue in Chicago’s North Lawndale neighborhood. Originally rooted in the Chicago’s…
West Loop Art Fest
Experience one of Chicago’s best neighborhood festivals at the West Loop Art Fest, a vibrant two-day celebration of art, creativity, culture, and community in the…
Thirsty Ears
Thirsty Ears is Chicago's only classical music street festival, now in its 11th year. The festival features two days of stellar ensembles and soloists, craft…
Zoo Uncorked
Enjoy Zoo Uncorked, an unforgettable adults-only evening at Brookfield Zoo Chicago featuring cocktails, live music, and the rare chance to see the animals after dark.…
The Chinatown Adventure Food Tour
Immerse yourself in the vibrant flavors and rich history of Chicago’s Chinatown on our top-rated TripAdvisor food and culture tour. Enjoy seated dining at five…
3rd Fridays Free Admission Night
Free Admission Museum Nights take place every third Friday of each month from 5 pm to 8 pm! The tour will start at 6:00 pm…
Opera at the Garden
Paradise Garden Logan Square, a community garden at 2214 N Drake Ave in Chicago, presents Classical Open Mic. Opera, classical guitar, that trombone solo you've…
Wicker Park Farmers Market
The Wicker Park Farmers Market will return on May 3 for its 26th outdoor season. The market will be open from 8 a.m. to 2…
Adults Night Out: Crafted at Lincoln Park Zoo
Chicagoland crafters, this one’s for you! Adults Night Out: Crafted is a night for craft enthusiasts ages 21+ to get hands-on with your favorite crafts…
The Banchet Awards’ Cluck ‘N Bubble
THE BANCHET AWARDS TO HOST INAUGURAL CLUCK ‘N BUBBLE, A FRIED CHICKEN AND CHAMPAGNE EVENT FEATURING TOP CHICAGO CHEFS What: Cluck ‘N Bubble Fried Chicken…
Street Foods of Pilsen Food Tour
Cruise with us down to the Lower West Side neighborhood of Pilsen that Forbes calls one of the “12 Coolest Neighborhoods Around the World” for…
The Dramatic Improv Festival
The Dramatic Improv Festival returns to Chicago, August 20-23 for four days celebrating the art of grounded, human, emotionally authentic improvisation. Hosted by Theatre Momentum,…
Third Friday at Zhou B Art Center
Explore our building. Chat with the artists. Let your curiosity set the pace. Sift through multiple galleries and studios; with 50 artists in residence, each…
Kacey Musgraves – Middle of Nowhere Tour
Kacey Musgraves has added a second Chicago show at the United Center on Thursday, August 20, 2026, due to overwhelming demand. This performance now serves…
WILLIS – 2026 Tour
The surf-rock band WILLIS is performing at the House of Blues Chicago on Friday, August 21, 2026. Support: The Flooks.
Millennium Park Summer Workouts
Participants are asked to bring their own workout mat The workout program takes place on the Great Lawn and Wrigley Square in Millennium Park on…
Kip Moore & Billy Currington Live In Concert
Country music star Kip Moore is bringing his co-headlining "Live In Concert" tour with Billy Currington to Chicago in late summer 2026. Special Guest: Kenny…
Spotlight Reading Series: A Century of Black Progress
Featuring the most ambitious programming to date, Court Theatre’s 2026 landmark Spotlight Reading Series is organized around the theme “A Century of Black Progress” and…
Pandemonium, Please Hold
The Second City’s 114th Mainstage Revue Pandemonium, Please Hold is a loud, fast, and gloriously unhinged night of comedic mayhem. The Second City’s six-person cast…
Summer Screenings: On the Road Again
In celebration of the 100th anniversary of the founding of Route 66—America’s most iconic highway—this year’s Summer Screenings program will pay homage to the classic…
Tangible Sound: Arrival to a Higher Ground
Imagine walking inside the thunderous sound of a taiko drum or feeling enveloped by the sinuous sounds of a saxophone, cello, or bass. What if…
Theater of the Mind
Now Extended Multiple experiences per day at the Reid Murdoch Building, 333 N LaSalle Visit TheateroftheMindChicago.com for dates, times, and tickets Created by David Byrne…
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
