August events in Chicago are some of the most unique you’ll find all summer long.
Maybe it’s because folks are trying to squeeze in every last bit of summer, but the month is packed with everything—from charitable fundraiser events like the Chicago Ducky Derby to food and street festival competitions galore.
Whether you’re popping out to the latest party or sitting back at the beach, there’s no shortage of summer things to do and Chicago activities to enjoy this August.
Keep scrolling this guide for the best August events and experiences to check out this month in Chicago.
The Best Things to Do in Chicago This August
Use the navigation below to explore must-attend August events, recurring summer experiences, and curated picks. Bookmark this guide—new updates and hidden gems may be added throughout the month.
Top Events: Must-attend events of the month.
Recurring Activities: Regular events worth adding to your calendar.
The Curated List: Personal recommendations for unique Chicago experiences.
Top August Events & Festivals in Chicago
Discover the biggest summer festivals and street fairs happening throughout the city.
August Chicago Street Festivals
August is full of exciting summer street and neighborhood festivals. Highlights include:
July 31 – August 3, 2025: Fiesta Del Sol
August 1 – 2, 2025: Jeff Fest
August 8 – 10, 2025: Ginza Festival
August 8 – 10, 2025: Serb Fest
August 9, 2025: Taste of Albany Park
August 9, 2025: LATINXT
August 9 – 10, 2025: Printers Row Lit Fest
August 14 – 17, 2025: Taylor Street Festival
August 15 – 17, 2025: Glenwood Avenue Arts Fest
August 16 – 17, 2025: The Great American Lobster Fest
August 17, 2025: Roscoe Village Porchfest
August 22 – 24, 2025: Edison Park Fest
August 22 – 24, 2025: Taste Of Greektown
August 22 – 24, 2025: Pizza City Fest
August 22 – 23, 2025: Chicago House Music Festival
August 23 – 24, 2025: Bucktown Arts Fest
August 23 – 24, 2025: Lakeview Taco Fest
August 23 – 24, 2025: Eeeeeatscon
August 28 – 31, 2025: Chicago Jazz Festival
August 29 – 31, 2025: North Coast Music Festival
August 29 – 31, 2025: ARC Music Festival
August 30 – 31, 2025: WingOut Chicago
August 29 – September 1, 2025: Taste of Polonia
Lollapalooza
July 31 – August 3, 2025 | Grant Park
Lollapalooza returns to Chicago with four days of non-stop music, food, and cultural energy. Featuring over 170 artists across eight stages, the festival draws crowds from around the world to experience some of the biggest names in music. Enjoy skyline views, curated food vendors, immersive art installations, and unforgettable moments at one of the city’s signature summer festivals.
The Black Women’s EXPO
August 1 – 3, 2025 | McCormick Place
Celebrate and experience 30 years of sisterhood, community, and culture at the Black Women’s EXPO. This 3-day-long exposition brings together entertainment and education that addresses the needs of Black women and families. Attendees can experience seminars, talks, and music from well-known speakers along with a marketplace for emerging and small businesses.
Chicago Ducky Derby
August 7, 2025 | Pioneer Court, 401 N Michigan Ave.
Watch thousands of yellow rubber ducks float down the Chicago River for charity this August in Chicago. The annual Chicago Ducky Derby is a fundraising event that benefits the Special Olympics Illinois. The event is free to attend, and it costs $10 to adopt a deck and enter the race.
Northalsted Market Days®
Friday, August 8 – Sunday, August 10, 2025 | Halsted St. from Belmont to Addison
One of the most highly anticipated Chicago summer street festivals, Northalsted Market Days takes over the Northalsted(Boystown)/Lakeview neighborhood this August for a jam-packed weekend. The festival draws crowds from around the world to experience the landmark of Chicago’s LGBTQ+ community. Headliners for this year’s festival include Keke Palmer, David Archuleta, Monét X Change, Joe Dombrowski, RuPaul’s Drag Race winner Sasha Colby, and Saucy Santana. Along with the live performances, attendees can also expect over 300 LGBTQ+ vendors ranging from food and drinks to nonprofits.
The Bud Billiken® Parade
August 9, 2025 | Dr. Martin Luther King Jr. Drive, starting at 35th Street south to 55th Street in Washington Park
The Bud Billiken Parade is the largest African American parade in the U.S., drawing thousands each year to Chicago’s South Side. Now in its 96th year, the two-mile celebration features music, dance, and a Royal Court of youth essay winners, with this year’s Grand Marshal being Chicago’s own LaRoyce Hawkins. The parade concludes in Washington Park with a festival featuring a variety of vendors, school supplies, and community resources.
Chicago Air and Water Show
August 15 – 17, 2025 | North Ave. Beach and along the Lakefront Experience the thrill of twist, turns, stunts The Chicago Air and Water Show. Presented by the City of Chicago, this is the largest free show of its kind in the United States. The show can be viewed along the lakefront from Fullerton to Oak Street, with North Avenue Beach as the focal point.
Bike The Drive
August 31, 2025 | Pioneer Court, 401 N Michigan Ave
Ever wanted to bike down DuSable Lake Shore Drive? Now’s your chance, join 20,000+ riders for up to 30 car-free miles, followed by a post-ride festival in Grant Park. This annual ride supports Active Transportation Alliance, a nonprofit advocating for better walking, biking, and transit in Chicago.
Chicago SummerDance
August – September 2025 | Various Locations
Dance under the stars at Chicago SummerDance, a beloved free event series featuring live music and dance lessons in parks across the city. From salsa and swing to line dancing and bachata, each event invites participants of all skill levels to learn a new style and enjoy vibrant community celebrations. Expect themed nights, cultural showcases, and family-friendly activities throughout the summer.
Millennium Park Summer Film Series
August – September 2025 | Various Locations
Looking for one the best free things to do this summer in Chicago? Watch free outdoor movies all summer long at the iconic Jay Pritzker Pavilion in Millennium Park. Bring a blanket or lawn chair and enjoy a mix of classic and contemporary films shown on a state-of-the-art 40-foot LED screen. A must for anyone looking for free things to do in Chicago in August.
Millennium Park Summer Music Series
August 4 & 7, 2025 | Jay Pritzker Pavilion, Millennium Park
This free concert series brings a diverse lineup of local and national artists to one of Chicago’s most iconic outdoor venues. Held on select evenings, the Millennium Park Summer Music Series features a diverse range of music, from jazz and indie rock to global rhythms and experimental sounds. Bring a blanket, pack a picnic, and enjoy warm nights filled with live music in the heart of downtown.
Maxwell Street Market
August – October | West Maxwell Street &, S Halsted St
On select Sundays, enjoy this free event in Chicago. The Maxwell Street Market will open, featuring an eclectic mix of foods and finds. This year’s edition will also feature live entertainment and programming from cultural partners, incorporating nearby businesses and restaurants, including several “Maxwell Street originals” with longstanding ties to the neighborhood.
Chicago Farmers Markets
August – October | Various Locations
Now through the fall, you can find fresh fruit, vegetables, flowers, baked goods, and more at various neighborhood farmers’ markets in the city of Chicago.
Summer Saturday Fireworks at Navy Pier
August 2, 9, 16, 23, 30 | Navy Pier
If you’re looking for free things to do in August in Chicago, nothing beats watching the summer fireworks at Navy Pier. This outdoor event is perfect for groups of all ages to enjoy.
Looking for Chicago events and things to do in Chicago this weekend? Check out the events calendar.
Ongoing Things to Experience in Chicago in August
Looking for things to do in Chicago in August that are available all month long? Here’s a round-up of ongoing attractions and seasonal experiences to check out this month.
- Architecture Boat Tour: Experience Chicago’s stunning skyline on a Chicago boat tour, a perfect outdoor activity for warm weather.
- Chicago Beaches: Visit one of the many beaches in Chicago before the warm weather is gone.
- Flyover in Chicago: Marvel at Chicago’s skyline and lakefront from a thrilling 30-minute immersive ride. Located at Navy Pier.
- Chicago Crime & Mob Bus Tour: Step into the city’s darker history and discover infamous crime spots.
- Chicago Rooftop Pools: Soak up the sun and city views at rooftop pools—perfect for a luxe summer escape.
- 360 CHICAGO Observation Deck Admission: Tower above Chicago from the 94th floor of 875 N. Michigan Avenue, enjoying panoramic views, grab a cocktail at CloudBar, or try the exhilarating TILT experience.
- Museum Free Days: Take advantage of free or discounted admission at museums.
- Interactive Museums: Capture Insta-worthy photos in interactive museums like the Museum of Ice Cream or the colorful Color Factory.
- Weekday Events: Break your routine with free movies in the park, neighborhood festivals, happy hour specials, and concerts happening Monday through Thursday.
The Curated List of Chicago Events in August
Here’s The Haute Seeker’s curated list of the best events, activities, and coolest events to check out during August.
The Sweetest Season: A Gathering of Indigenous Creativity at Goodman Theatre
What: Now in its fourth year, this two-day celebration of Indigenous creativity features a Friday night Two-Spirit drag show and a Saturday lineup of workshops, panels, live music, comedy, and more. Presented in partnership with the Gichigamiin Indigenous Nations Museum.
When: August 1–2, 2025
Link for more information: The Sweetest Season at Goodman Theatre
Chicago Bears Family Fest at Soldier Field
What: Watch the Chicago Bears’ first team practice of the season at Soldier Field with family-friendly fun, giveaways, and on-field activities for all ages.
When: August 3, 2025
Link for more information: Chicago Bears Family Fest
The Bridge: A Benefit Concert for Semicolon Books at Lincoln Hall
What: Audiotree presents a night of music and poetry to benefit Semicolon Bookstore, featuring Jamila Woods, Shawnee Dez, Senite, and more. Hosted by Raych Jackson with special guest m.e.h. and poems by Naira Bills.
When: August 8, 2025
Link for more information: The Bridge at Lincoln Hall
2nd Annual Taste of Bronzeville at XS Tennis Village
What: This community-driven food festival brings the spirit of a family barbecue to life with incredible eats, local entertainment, and an atmosphere of togetherness through Black owned businesses. Enjoy delicious bites from Bronzeville restaurants you may not know yet and support neighborhood businesses in one fun-filled day.
When: August 9, 2025
Link for more information: The Way It Is Tour
Jeezy TM:101 Live with Color of Noize Orchestra at The Chicago Theatre
What: Hip-hop legend Jeezy performs his iconic debut album Let’s Get It: Thug Motivation 101 with orchestral arrangements from the Color of Noize Orchestra and guest DJ Drama.
When: August 9, 2025
Link for more information: Jeezy at The Chicago Theatre
The Chicago R&B Block Party at Recess
What: A 21+ outdoor day party with R&B music, live performances, DJs, food, games, and good vibes. Hosted by WGCI’s Tone Capone, featuring Ben One and top Chicago DJs.
When: August 10, 2025
Link for more information: R&B Block Party
Uno Social Club Game Night at The Empty Bottle
What: UNO is bringing it’s social club to several major cities this summer, including Chicago. This lively night will be filled with music, games, and drinks hosted by Kerry Stevens with beats by DJ Raven Wright.
When: August 13, 2025
Link for more information: Uno Social Club at The Empty Bottle
Terry Hunter’s Birthday Party by The Chosen Few DJs at Wintrust Arena
What: Celebrate the legendary DJ’s birthday with an epic show featuring Yolanda Adams, Jazzy Jeff, Rakim, Estelle, Deon Cole, The Chosen Few DJs, and more.
When: August 16, 2025
Link for more information: Terry Hunter’s Birthday Bash
West Town Night Market at Midwest Coast Brewing
What: Shop handmade goods, enjoy food and drinks, and soak up night market vibes under the lights at Midwest Coast Brewing. Free entry; dog and kid-friendly!
When: August 21, 2025
Link for more information: West Town Night Market
August in Chicago: What to Expect (and Wear)
What’s the weather like in Chicago during August?
August weather is still very much summer weather. Daytime highs are typically in the low-to-mid 80s°F, with plenty of sunshine and occasional humid days. Evenings may cool down just slightly for a very light jacket or sweater.
Is August a good time to visit Chicago?
Is August a good time to visit Chicago?
Definitely! August has a ton of summer festivals to still enjoy throughout the month. Towards the end of the month, the city will begin to feel a bit quieter, especially during the week as back-to-school season slowly starts to creep in.
What should I wear in Chicago in August?
What should I wear in Chicago in August?
Keep things light and breathable. Think shorts, sundresses, and airy shirts are your best friends. Bring a light jacket or sweater for breezy nights by the lake or indoor venues with AC.
What to Look Forward to in August
If July is the peak, August is the encore. Expect late-summer block parties, music festivals, art shows, and food fests that celebrate Chicago’s neighborhoods and cultures. Soak it all in! Fall will be here before you know it.
