14 Things to Do in Chicago This Week · October 1–4, 2026

Music & Nightlife

Stephanie Aaron Quartet

Chicago vocalist Stephanie Aaron performs the songs she loves with her quartet on Chicago's North Shore.

Thursday, October 1, 2026 · North Shore

DENNETT (360° SET) - Back to the Roadhouse Tour

DENNETT performs a 360° set with PAPAJAY and NOLA at Concord Music Hall on the Back to the Roadhouse Tour.

Friday, October 2, 2026 Doors @ 10:00 PM · Concord Music Hall

John Heffron at Chicago Improv

Stand-up comedian John Heffron performs five shows over three nights at the Chicago Improv.

Thursday, October 1 – Saturday, October 3, 2026 · Chicago Improv

Drunk Dracula in Chicago

Drunk Shakespeare Chicago's Halloween spin puts actors in a Dracula production where one performer downs multiple shots before the show begins.

Wednesday, September 30 – Friday, November 7, 2026 · Drunk Shakespeare Chicago

Arts & Culture

Mernet Larsen: Situational Awareness at The Arts Club of Chicago

Chicago painter Mernet Larsen presents her distinctive figurative work in a solo exhibition at the historic Arts Club of Chicago.

Thursday, October 1, 2026 (through December 18, 2026) · The Arts Club of Chicago, 201 East Ontario Street

Pope.L: No Thing Skin Sets at Corbett vs. Dempsey

A solo exhibition by provocative conceptual artist Pope.L at Corbett vs. Dempsey gallery in the West Loop.

Thursday, October 1, 2026 (through October 31, 2026) · Corbett vs. Dempsey, 2156 W. Fulton Street, Chicago

Topdog / Underdog at Steppenwolf Theatre

Suzan-Lori Parks' Pulitzer Prize-winning play runs through December at Steppenwolf Theatre in Lincoln Park.

Thursday, October 1, 2026 (through December 6, 2026) 7:30 PM · Steppenwolf Theatre, 1650 N Halsted St, Chicago

Kino, Kaffee und Kuchen

German-language film screening every Saturday at the DANK Haus, with coffee and cake starting at 10:30 AM followed by a short film and feature.

Saturday, October 3, 2026 10:30 AM · DANK Haus German American Cultural Center, 4740 N. Western Ave., Chicago

Festivals & Special Events

FAHSC 40th Anniversary Gala & Filipino American History Month Kickoff

Closing reception for the Filipino Nurses in America exhibit plus Filipino American History Month kickoff and the Filipino American Historical Society of Chicago's 40th Anniversary Gala.

Saturday, October 3, 2026 4:00 PM – 7:00 PM · Trickster Cultural Center, 190 S Roselle Rd, Schaumburg, IL

Chicago Vampire Ball 2026

An annual Halloween costume ball at Artifact Events featuring live performances, DJs, and elaborate vampire-themed decor.

Friday, October 9, 2026 · Artifact Events, Chicago

Free Events

Puerto Rican Arts Alliance: Studio Arts Program

Free open art studio for people ages 12–25 to explore painting, drawing, printmaking and more at El Rinconcito with an artist and counselor on hand.

Saturday, October 3, 2026 10:30 AM – 2:30 PM · El Rinconcito

Chicago 26.2 Cheer Zone in Pilsen

Join Family Style RC and Read & Run Chicago on Loomis Street in Pilsen for the ultimate book-lover cheer zone along the Bank of America Chicago Marathon route.

Sunday, October 11, 2026 5:15 AM – 2:30 PM · Loomis Street, Pilsen, Chicago

Food & Drink

Perry's Steakhouse Flashback Friday – 79-Cent Specials

Perry's Steakhouse offers 79-cent lunch specials at all Chicago-area locations for one day only, including its famous slow-smoked pork chop.

Friday, October 2, 2026 · Perry's Steakhouse, Chicago-area locations

Outdoors & Active

Chinatown Run/Walk Shakeout Before 26.2

Experience the marathon route through Chinatown with Family Style RC, Read & Run Chicago, and the Chinatown Branch of Chicago Public Library ahead of the big race.

Saturday, October 10, 2026 9:30 AM – 11:30 AM · Chinatown, Chicago