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

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  • 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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Chicago proves that the best summer memories don’t have to come with a price tag. From lakeside festivals and open-air concerts to museum gems, there’s no shortage of free ways to experience the city’s vibrant culture and energy. Whether you're a local looking for a new weekend escape or a visitor on a budget, these picks show that Chicago is always open for fun — without breaking the bank.

So grab your sunscreen, pack a picnic, and start exploring!