One of the best parts of living in Chicago? Summer! The city comes alive in a way that is unique only to Chicago: every neighborhood buzzing with events, lakefront strolls, and block parties that make you fall in love with the city all over again. As a Chicago real estate broker, I love to remind my clients that buying a home in Chicago isn’t just about the property, it’s about a lifestyle.
Here is a list of some of my favorite events to celebrate summer 2025 in Chicago!
Music Festivals
Chicago’s summer music festival calendar is legendary! A few favorites this year:
- Lollapalooza – Huge 4‑day music fest in Grant Park, July 31–August 3, 2025. Headliners: Olivia Rodrigo, Sabrina Carpenter, Tyler The Creator, Korn, and more
- Grant Park Music Festival – Free outdoor classical performances every Wednesday, Friday, and Saturday from June 11 through August 16 at Pritzker Pavilion
- Riot Fest (20th anniversary!) – Punk/rock festival at Douglass Park, Sept 19–21 featuring Green Day, Blink‑182, Weezer, Jack White, Sex Pistols, and more
Neighborhood Street Fests
Chicago’s neighborhoods host countless smaller fests during June through August, perfect for exploring local food, music, art, and community vibes.
- Square Roots Craft Brew & Music Festival (Lincoln Square) – July 11–13, featuring craft beers, local artists, live music, and family areas
Southport Art Fest (Lakeview) – July 12–13, showcasing local art, food vendors, and live entertainment - Taste of River North (River North) – July 18–19, celebrating neighborhood eateries with food stalls, cocktails, live music, and artists
- Taste of Lincoln Avenue (Lincoln/Fullerton corridor) – July 25–26 marks its 40th anniversary with entertainment and street food
- Wicker Park Fest (Wicker Park) – July 26–28, local musicians, arts and crafts, food trucks, and a festive neighborhood vibe
- Chinatown Summer Fair (Chinatown) – July 26–27 with lion dances, cultural performances, and Chinese cuisine
- Bud Billiken Parade & Picnic (Bronzeville/Washington Park) – August 9 (second Saturday), large-scale back‑to‑school parade with picnic festivities
- Northalsted Market Days (Lakeview, Boystown) – August 9–10, one of the biggest street fairs in the Midwest, with food, live music, vendors
- Taste of Greektown (Greektown, Near West Side) – mid‑August culinary street fest with Greek food, music, and family-friendly entertainment
- Printers Row Literary Festival (Printers Row, South Loop) – early September, downtown street fair dedicated to books, authors, and family activities
- Andersonville City Made Fest (Andersonville) – September, a community street fair showcasing local makers, boutiques, crafts, food and live music
- Fulton Fest (Near West Side, Fulton Market) – September, neighborhood businesses, food trucks, entertainment, and street art
Movies in the Park
More than 100 parks across the city host free outdoor movie nights. More information here.
Green Space Galore
From family-friendly splash pads at Maggie Daley Park to shaded strolls through the Garfield Park Conservatory, Chicago's park system shines in the summer. We always encourage new buyers to explore the city’s green spaces because they're part of what makes living here feel so balanced.
Thinking of making a move this summer?
Whether you’re buying your first condo in Lincoln Park, trading up to a bigger home, or relocating to a new part of Chicago, I’d love to help you find a place that fits your lifestyle – one that lets you make the most of everything summer in Chicago has to offer. Here’s to long days, warm nights, and finding your perfect spot in the city we all love!
