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Your Guide to Chicago in August 2025

Posted on July 31, 2025   |   Updated on September 30, 2025
Emily Mack

Emily Mack

Lollapalooza.

Lollapaloozers rocking out. (Photo by Erika Goldring/WireImage)

August is Lolla season in Chicago — but there’s lots of other fests and events going on. Here’s your monthly guide to make the most of the end of summer.

City Cast

Your Guide to August 2025 in Chicago

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🎉 Festivals

Lollapalooza starts today in Grant Park and goes through Aug. 3. One-day tickets are still available for $189, but if you prefer a slightly chiller concert experience, consider these Lolla aftershows. All the ones at Salt Shed are sold out, but you can still make their outdoor Wilco show on Aug. 10!

Other music fests coming up include:

Upcoming street fests include:

The four-day Fiesta del Sol also kicks off today in Pilsen, but organizers are worried that U.S. Customs and Immigration Enforcement might show up unannounced. Despite these fears, the city’s largest Latino fest is expected to draw over 1 million attendees.

🍗 Your guide to Chicago food fests

🌳 Get Outdoors

The Chicago Shakespeare Theatre is putting on “A Midsummer Night’s Dream” at multiple parks till Aug. 17. “Love’s Labour’s Lost” runs in Touhy Park Aug. 1-3. For the kids, “Book Up!” and “Ice Cream Circus!” are running at multiple parks till Aug. 10 and Aug. 24, respectively.

💐 Your rest-of-summer theater guide

Other outdoor events include:

💪 Your guide to exercising outdoors in Chicago

🗞️ In the News

With City Council on recess, the political focus this month is on CPS. The school district must finalize its yearly budget by Aug. 28 while facing a $734 million deficit.

🍎 Your CPS budget explainer

Of course, it’s not just CPS struggling with budget holes. Will Illinois lawmakers call a special session to address the transit funding cliff? We still don’t know!

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