40+ Things To Do In Chicago This August: Concerts, Festivals, Street Fairs & More

CHICAGO — From music under the stars to vibrant neighborhood festivals, Chicago is turning up the heat this August with more than 40 incredible things to do across the city. Whether you’re a die-hard live music fan, a foodie in search of the next street fest, or a parent planning a weekend out with the kids — there’s something happening every week of the month.

Here’s your ultimate guide to August’s most exciting events:

Millennium Park Summer Music Series

When: Mondays and Thursdays through August 8
Where: Jay Pritzker Pavilion, Millennium Park
What to Expect: Free live music performances spanning indie, jazz, blues, world music, and more in one of the most iconic open-air venues in the country.

Chicago Shakespeare in the Parks: “The Comedy of Errors”

When: Through August 25
Where: Various Chicago parks
Details: This summer’s free citywide tour features a 45-minute musical take on Shakespeare’s classic comedy, traveling through 18 neighborhood parks with live performances by a cast of local artists.

Lincoln Park Greek Fest

When: August 2–4
Where: St. George Greek Orthodox Church, Lincoln Park
Why Go: Authentic Greek food, live traditional music, and cultural dance performances in a family-friendly atmosphere.

Ruido Fest 2025

When: August 16–18
Where: Union Park
Highlight: The Latin alternative music festival returns with three days of reggaeton, cumbia, rock en español, and hip hop, featuring major acts like Café Tacvba and Nicki Nicole.

Navy Pier Fireworks + Free Live Music

When: Every Wednesday & Saturday
Where: Navy Pier
What’s Special: Catch free fireworks after sunset, often paired with live music performances at the Wave Wall Stage and Beer Garden.

Chicago Hot Dog Fest

When: August 9–11
Where: UIC Soccer Fields
Why It’s Tasty: Celebrate the city’s beloved hot dog with dozens of vendors, plus music and family activities hosted by the Chicago History Museum.

Grant Park Music Festival

When: Through August 17
Where: Millennium Park
About: Enjoy the final concerts of this free classical music series featuring the Grant Park Orchestra and Chorus, with programs ranging from Mahler to movie scores.

Northalsted Market Days

When: August 10–11
Where: North Halsted Street, Boystown
Party Vibe: One of the biggest street fests in the Midwest, Market Days spans six blocks with multiple live music stages, food vendors, art booths, and a vibrant LGBTQ+ celebration.

Chicago Air and Water Show

When: August 17–18
Where: North Avenue Beach
Sky High Energy: Don’t miss the U.S. Navy Blue Angels and other jaw-dropping aerial performances over Lake Michigan. It’s one of the largest free air shows in the U.S.

More Must-Attend Events in August

Lollapalooza Aftershows – Catch intimate sets at city venues Aug 1–4
Bronzeville Summer Nights – Aug 16, featuring live jazz and shopping
Logan Square Food Truck Social – Aug 23–25 with 25+ food trucks
Chicago Ducky Derby – Aug 8 at Columbus Drive Bridge
Sundays on State – Aug 11, open streets celebration downtown
Chicago Jazz Festival – Kicks off late August into Labor Day weekend
Edgewater Arts Festival – Aug 24–25, fine art, music, food trucks
Movies in the Parks – Family-friendly films screened across the city
Music Box Garden Series – Outdoor films and music on Southport
Bud Billiken Parade – Aug 10, the nation’s largest African-American parade

Why It’s a Perfect Month for Music Lovers

From Grant Park symphonies to global rhythms at Ruido Fest, this August proves once again that Chicago is a summer music capital. Whether you’re looking to sway to acoustic sets in the park or catch full-scale festivals with food and dance, the options are as diverse as the city itself.

Got a favorite August event or music fest we missed? Let us know at ChicagoMusicGuide.com and we may feature it in next month’s picks!