Top Things to Do in Chicago in September

1. Taste of Chicago

The world’s largest food festival takes over Grant Park every September, offering samples from top restaurants, live music, rides, and a festive atmosphere perfect for families and food lovers alike.

Nearby bites:

Lou Malnati’s – a deep-dish classic.

The Dearborn – modern American comfort food near the Loop.

2. Riot Fest – 20th Anniversary

Rock out at Riot Fest in Douglass Park from September 19 to 21. This year’s epic headliners include Blink‑182, Weezer, Green Day, alongside Jack White, the Sex Pistols, Rilo Kiley, and more—a major celebration of two decades of punk and alternative music.

Pro Tip: Pair your festival look with fresh jewelry—stop by Identity Body Piercing for some bold new pieces before you hit the shows.

3. Chicago Half Marathon & 5K

Want a scenic run? Join thousands pacing along Lake Shore Drive for the Chicago Half Marathon or 5K. Known as “The People’s Race,” this iconic event winds along beautiful lakefront views.

Fuel up nearby:

Yolk (South Loop) – perfect for a pre-race breakfast.

Beatrix – healthy and energizing post-run brunch.

4. Chicago River Swim

Making history, the Chicago River Swim returns on September 21—marking the first open-water swim in nearly a century. Participants will swim from the Dearborn Street Bridge to Clark Street Bridge, celebrating environmental progress and supporting youth swim education.

5. Guided Architecture River Cruises

Take in Chicago’s skyline from the water with architecture cruises. Options range from 1.5-hour guided tours to shorter family-friendly rides with commentary—and some even include a full-service bar on board.

Nearby bites:

Porter Kitchen & Deck – stylish American fare on the river.

RPM Seafood – upscale dining with skyline views.

6. Stroll the Riverwalk & Visit Museums

Take a relaxed walk along the Chicago Riverwalk, enjoy the shops, cafes, and views—and explore nearby cultural gems like the Art Institute, Field Museum, or the Lincoln Park Zoo (free entrance!).

7. Explore Cultural Festivals & Tours

September brings a variety of free and engaging experiences—such as “Under the Picasso” performances in Daley Plaza, cultural center tours, and history walks like the Lincoln Park Blues & Gangster tour.

8. Outdoor Performances & Art Experiences

Check out AR-inspired art in Millennium Park—”Augmented Chicago” offers virtual artwork overlays across park spaces, blending tech and creativity in a uniquely immersive way.

Quick Snapshot:

– Taste of Chicago

– Riot Fest

– Chicago Half Marathon, River Swim

– River Cruises, Riverwalk, Museum Visits

– Walking tours, “Under the Picasso” events

🎭 Neighborhood Exploration: Wicker Park & Roscoe Village

September is a great time to explore Chicago’s unique neighborhoods.

Wicker Park:

Known for its music, art, and boutique shopping, it’s also home to Identity Body Piercing’s flagship studio (est. 2013). After updating your look with a new piercing or jewelry styling, grab coffee at The Wormhole or dinner at Big Star for tacos and margaritas.

Roscoe Village:

Nicknamed the “Village Within the City,” this laid-back neighborhood is perfect for strolling tree-lined streets, boutique shopping, and visiting the second Identity Body Piercing location. Cap off your visit with comfort food at Kitsch’n on Roscoe or pizza at Commonwealth Tavern.

September in Chicago balances early-fall charm with cultural vibrancy. Whether you’re a foodie, music lover, nature fan, or art aficionado, the city offers an unforgettable lineup.

🌟 Make September Unforgettable

Chicago in September blends music, culture, food, and style into one unforgettable experience. Whether you’re cheering at Riot Fest, tasting the city at Grant Park, or strolling through Roscoe Village, make sure to add Identity Body Piercing to your plans. With studios in Wicker Park and Roscoe Village, we’re here to help you start the season with style, confidence, and a look that’s all your own.

👉 Ready to elevate your back-to-school or fall style? Book your piercing or jewelry styling appointment today.

No appointment needed for shopping jewelry or piercing services but you are welcome to book online for either location!