9 Things to Do in Chicago This Week · October 29–November 1, 2026

Music & Nightlife

The Damned

Riot Fest presents punk legends The Damned with The Flamin' Groovies and The Courettes.

Saturday, October 31, 2026 Doors @ 7:00 PM · Concord Music Hall

Day of the Dowd 3

Gerald Dowd honors the departed and fights to keep Chicagoans fed with Day of the Dowd 3.

Sunday, November 1, 2026 · Robert's Westside

Joshua Radin with Raye Zaragoza

Joshua Radin plays two nights at City Winery Chicago with Raye Zaragoza.

Saturday, November 7, 2026 and Sunday, November 8, 2026 · City Winery Chicago

Date Night

Candlelight: Halloween Classics

A candlelit concert performing Halloween classics at The Congress Plaza Hotel.

Friday, October 30, 2026 · The Congress Plaza Hotel & Convention Center

Festivals & Special Events

Boos & Booze Chicago Friday Halloween Bar Crawl

A Friday Halloween bar crawl through River North and the West Loop.

Friday, October 30, 2026 · River North & West Loop

Block Club Chicago's South Side Health & Wellness Fest

A community health and wellness fest on the South Side, with Read & Run Chicago as a participating organization.

Saturday, November 7, 2026 9:00 AM – 3:00 PM

Arts & Culture

Amir K

Comedian Amir K performs four shows across the Friday and Saturday weekend.

Friday, October 30 – Saturday, October 31, 2026 · Chicago Improv

Turning Pages: Author Talk with Roberta Rubin

Longtime Book Stall owner Roberta Rubin discusses her memoir Turning Pages: The Life and Times of a Bookseller. Tickets $6–$8.

Tuesday, November 3, 2026 6:00 PM – 7:00 PM · American Writers Museum, 180 N. Michigan Ave.

Food & Drink

Mask Bar Fundraising Happy Hour at Scratch Goods

A BYOB self-care happy hour in the West Loop fundraising for Read & Run Chicago programming.

Wednesday, November 11, 2026 5:30 PM – 6:30 PM · Scratch Goods, West Loop