Your Guide to Chicago in August 2025

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.

🎉 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:

• Chicago House Music Festival and Conference | Aug. 22-23 | Loop
• Thirsty Ears Music Festival | Aug. 23-24 | Ravenswood
• Chicago Jazz Festival | Aug. 28-31 | Loop
• ARC Music Festival | Aug. 29-31 | Near West Side
• North Coast | Aug. 29-31 | Bridgeview
  

Upcoming street fests include:

• Jeff Fest | Aug. 1-2 | Jefferson Park
• Taste of Albany Park | Aug. 9
• Printer’s Row Art Fest | Aug. 9-10
• Northalsted Market Days | Aug. 8-10
• Glenwood Avenue Arts Fest | Aug. 15-17 | Rogers Park
• The Great American Lobster Fest | Aug. 16-17 | Near North Side
• Roscoe Village Porchfest | Aug. 17
• Adults Night Out: Block Party | Aug. 21 | Lincoln Park
• Edison Park Fest | Aug. 22-24
• Taste of Greektown | Aug. 22-24
• West Chicago Food Festival | Aug. 23
• Bucktown Arts Fest | Aug. 23-24
• Lakeview Taco Fest | Aug. 23-24
• Sangria Festival Chicago | Aug. 23-24
• Chicago Romanian Food & Folk Festival | Aug. 23-24 | West Ridge
• Eeeeeatscon | Aug. 23-24 | West Town
• Taste of Polonia | Aug. 29-Sept. 1 | Jefferson Park
• WingOut Chicago Aug. 30-31 | Lakeview

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.

🌳 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.

Other outdoor events include:

• Wooded Island Birding | Saturdays | Jackson Park | South Shore
• Chicago Scream Club | Sundays | North Avenue Beach | Lincoln Park
• Humboldt Park Arboreal Society (DJs) | Aug. 3, 17, 31
• Urban Rivers: Wild Mile Yoga | Aug. 3 | Goose Island
• Out Our Front Door | Aug. 5 | Rainbow Beach Park | South Shore
• Family Fishing | Aug. 9 | Canal Origins | Bridgeport
• Broadway in Chicago | Aug. 11 | Millennium Park
• Chicago’s Fabulous Fountains Bike Tour | Aug. 24 | Chicago History Museum | Lincoln Park

🗞️ 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.

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!

☝️ Also … be aware of extra traffic near Chicago and Halsted.