8 Things to Do in Chicago This Week · September 3–6, 2026

Outdoors & Active

Bike the Drive 2026

Chicago shuts down DuSable Lake Shore Drive to cars for a sweeping 30-mile scenic bike ride followed by a Grant Park festival — only once a year.

Sunday, September 6, 2026 · DuSable Lake Shore Drive / Grant Park

Festivals & Special Events

Printers Row Lit Fest 2026

The largest outdoor literary festival in the Midwest returns for a weekend of author talks, giveaways, and book culture.

Saturday, September 12, 2026 10:00 AM · Printers Row, Chicago

Riot Fest 2026

Icons, up-and-comers, and William Shatner converge at the annual punk and alternative music festival at Douglass Park.

Friday, September 18, 2026 – Sunday, September 20, 2026 · Douglass Park, Chicago

Music & Nightlife

Tony Rock at Chicago Improv

Comedian Tony Rock performs five shows over a full weekend at the Chicago Improv.

Friday, September 4, 2026 · Chicago Improv, Chicago

ARC After Dark: MAX DEAN, TOMMY PHILLIPS & MONTY KIDDO

A 360° late-night electronic music experience at Concord Music Hall featuring Max Dean, Tommy Phillips, and Monty Kiddo.

Friday, September 4, 2026 Doors @ 10:00 PM · Concord Music Hall, Chicago

Free Events

Wheeling Thursday Night Live – Petty Kings

Experience Petty Kings, a tribute to Tom Petty and the Heartbreakers, at this free outdoor summer concert series.

Thursday, September 3, 2026 · Wheeling, IL (North Shore)

Arts & Culture

Longer Than the Sky: Art of the Obama Years at Logan Center

A sweeping exhibition at the University of Chicago's Logan Center exploring art created during the Obama era, on view through October 11.

Thursday, September 3, 2026 · Logan Center Exhibitions, 915 E. 60th Street, Chicago

Food & Drink

Great American Lobster Fest Chicago 2026

Billed as the largest lobster festival in the Midwest, this seafood celebration comes to Chicago for the weekend.

Friday, September 4, 2026 · Chicago