This August, experience the best of Chicago — for free! Catch legendary jazz acts at a beloved outdoor music festival, dive into hands-on exhibits at an interactive science museum, or join a friendly local on a walking tour of one of the city’s most vibrant neighborhoods — all without spending a penny.
Chicago comes alive in the summer with a lineup of free events, from live music and outdoor performances to free museum days, neighborhood street fairs, and cultural festivals. Whether you're a visitor or a local looking for budget-friendly fun, there’s something for everyone.
Want more ideas? Explore our full guide to the best free and low-cost things to do in Chicago this summer.
Watch Chicago Air & Water Show
Photo credits to the rightful owner.
When?
August 15, 2025 - Friday: Practice Flyover
August 16, 2025 - Saturday: 10:30 a.m. to 3 p.m
August 17, 2025 - Sunday: 10:30 a.m. to 3 p.m
Where’s the best place to watch?
Restaurants near Lake Michigan
- Castaways
- Shore Club
- Theater on the Lake
- Whispers on Oak Street Beach
- Caffe Olivia
Rooftop bars with lake views
- Cindy’s
- The J. Parker
- Streeterville Social
Navy Pier
- Navy Pier Beer Garden
- Offshore Rooftop & Bar
- Harry Caray’s Tavern
Lake Michigan boat cruises
- Early Air and Water Show Preview - Brunch Cruise by City Cruises
- Air and Water Show Cruises by Chicago - Fireboat Tours
- Skyline Lake Tour from Navy Pier by - Shoreline Sightseeing
- Air and Water Show Kayak Tour by Kayak Chicago
- Chicago Air and Water Show Cruise from Tall Ship Windy
- Afternoon Air and Water Show Brunch Cruise by City Cruises
Observation decks
360 CHICAGO
Skydeck Chicago
Enjoy Chicago Jazz Festival
Chicago Jazz Festival, credit Patrick L. Pyszka
When?
Thursday, Aug. 28 – Opening Night
Henry Johnson
esperanza spalding
Friday, Aug. 29
Sarah Marie Young
Silvia Manrique and Marcel Bonfim
Patricia Barber
Monty Alexander
Saturday, Aug. 30
Ava Logan Quintet
Ernest Dawkins Ensemble New Horizon Redux
Gary Bartz & NTU Troop
Kermit Ruffins
Sunday, Aug. 31
Natalie Scharf Quintet featuring Paul Asaro
G. Thomas Allen
Ari Brown Quintet
Eliades Ochoa
Where?
Millennium Park – Jay Pritzker Pavilion
Watch movies under the stars
Abel Arciniega :: @tequilagraphics
When?
August 12, 2025 - Tuesday: Wicked (2024, PG)
August 19, 2025 - Tuesday : Pride and Prejudice (2005, PG)
Gates Opens at 5:00 PM
Start Time: 6:30 PM
Free admission enter at Michicgan Ave & Washington St
Where?
Millennium Park – Jay Pritzker Pavilion
Enjoy a free museum day
Listen to free live music
Credits to the rightful owner
When and Where?
Chicago SummerDance
June 29 – September 7, 2025
Grant Park and parks citywide
Millennium Park Summer Film Series
July 1 – August 26, 2025
Millennium Park
Tuesdays on the Terrace 2025
June 24 to August 26, 2025
MCA’s Anne and John Kern Terrace Garden
Gates open at 4:30 pm
Performances running from 5:30 pm until 8 pm
Honor Chicago history
Credits to the rightful owner
When?
Through August 25, 2025
Where?
Pullman National Historical Park
Watch the summer fireworks on the lakefront
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