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Your Guide to Chicago in June 2025

Posted on May 29, 2025   |   Updated on September 30, 2025
Emily Mack

Emily Mack

Participants during the 2024 Chicago Pride Parade.

Participants during the 2024 Chicago Pride Parade. (Photo by KAMIL KRZACZYNSKI / AFP)

Summer technically starts June 20 … but we know Summertime Chi is already in full swing. Get out there!

🌭 Street Fests

As always, Chicago is hosting some fun free street fests but don’t forget to donate at the gate!

🎶 Free Blues Music

Most Chicagoans know about the Blues Festival, but the Record Row Concert Series offers another free option on Thursday nights throughout the summer. It’s hosted by Willie Dixon's Blues Heaven Foundation — one of Chicago’s most unique museums

Kids enjoying the Puerto Rican People’s Parade in 2022.

Kids enjoying the Puerto Rican People’s Parade in 2022. (risingthermals / Flickr)

🇵🇷 Puerto Rican People’s Parade and Festival

We know the Puerto Rican celebration is here when the flags start flying from cars. This year, the 47th annual parade kicks off at 2 p.m. on Division and California. The fun goes on for four days in Humboldt Park. Festival admission is free on Thursday and costs $15+ over the weekend.

🏳️‍🌈

Chicago Pride

  • Pride Fest: June 21-22
    • A two-day street fest in Northalsted the weekend before the big parade, featuring live music on three stages, drag performances, 150+ vendors, and more. Headliners include Jesse McCartney and Deborah Cox.
  • Pride Parade: June 29
    • Last year, the Pride Parade was shortened to a two-mile route. This year, the parade follows that same path, starting on Sheridan and Broadway at 11 a.m.

Whether you’re at the official Pride events or not, expect Northalsted to be a non-stop party this month. Get ready, and try not to trip on the discarded feather boas. There’s also Backlot Bash in Andersonville the weekend of the parade. And yes, Jojo Siwa is performing.

🎥 Free Movies

  • For the kids: There are 40 family movie screening at parks throughout Chicago during June, plus three screenings outside of Wrigley Field at Gallagher Way.
  • For the grown-ups: Summer Screenings, hosted at the Chicago Cultural Center and the Chicago History Museum, kick off June 2 and are entirely free to the public. They feature flicks from around the world, and this season’s theme is Summer of Love.

🏙️ Enjoy the Riverwalk

Don’t forget: There are lots of ways to enjoy the river this summer 🛶

🍋 Plus: Summer Smash and NASCAR street closures

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