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what to do in chicago

October 28, 2026
Jacks Pumpkin Pop Up | Goose Island | Through November 1
October 28, 2026
420 Frankenstein | de Maat Studio Theatre | October 31
October 28, 2026
Haunted Halsted | Northalsted | October 31
October 28, 2026
WAMI Boos and Booze bar crawl | Citywide | October 30-31
October 28, 2026
Dom Dolla | Navy Pier | October 30-31
October 28, 2026
Azure after dark | Experience 868 Events | October 30
October 22, 2026
HighQ Gameshow Live | Bughouse Theater | October 23
October 21, 2026
Red Bull Setlist featuring Lil Yachty | Radius Chicago | November 24
October 21, 2026
House of the Exquisite Corpse | Steppenwolf Theatre | Through November 1
October 21, 2026
Nightmare on Clark Street | Stolen Saddle | Through November 1
October 21, 2026
Arts in the Dark | Columbus Dr | October 24
October 21, 2026
The My Budgies Comedy Variety Show | My Buddy's | October 23
October 21, 2026
Adler at Night | Adler Planetarium | October 21
October 16, 2026
HighQ Gameshow Live | Bughouse Theater | October 16
October 16, 2026
The Wellness Retreat | Northerly Island | October 17
October 16, 2026
Suki Waterhouse | Aragon Ballroom | October 17
October 16, 2026
Lincoln Square Greektober Fest | St. Demetrios Church | October 17-18
October 16, 2026
Crush Fest | Vin312 Winery | October 17
October 16, 2026
Charlotte De Witte | Navy Pier | October 16
October 8, 2026
HAMDI FC VS CHICAGO | Radius | October 10
October 8, 2026
Night of 1,000 Jack-o’-Lanterns | Chicago Botanic Garden | October 7 - 11
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The latest Chicago News

November 3, 2026
November is packed with things to do across Chicago.
November 2, 2026
Insider773 is teaming up with TBOX Bar Crawls to give Chicago residents a chance to win six tickets to the 30th Anniversary Twelve Bars of Xmas Crawl , taking place Saturday, December 12, in Wrigleyville.