| National Punctuation Day. |
| 6:00a Wolff's Flea Market & Antique Mall at Allstate. |
| 1:30p Ghosts Of Graceland Cemetery walking tour (Su). |
| 3:00p Chicago Bike Polo at Garfield Park. |
| 6:00p New cartoons on FOX. |
| 10:00p Monday Night Ride at Lincoln Monument. |
| 6:00p Chi Hack Night at 1871. |
| 6:30p Millennium Park Movies (Tu). |
| Pumpkin Farms at Many locations. |
| 11:00a EXPO Chicago at Navy Pier. |
| 9:00p South Park new episode on COM. |
| 10:00p Bittersweet at Berlin. |
| Horror Film Festival at The Patio Theater. |
| 6:00p Atomic Sketch Event at Green Eye Lounge. |
| 11:00a Terror in the Aisles at Patio Theater. |
| 1:00p * Jazz Festival at Hyde Park. |
| 5:45p Critical Mass at Daley Plaza. |
| Disclaimer. |
| 6:30p * Full Moon Fire Jam near lake south of Foster. |
| 10:00p Madonnarama at Berlin. |
| UniverSoul Circus at Washington Park. |
| Halloween in the Parks. |
| National Taco Day. |
| World's Best Costume Shop at Fantasy HQ. |
| 9:00p Movieoke at Whistler. |
| 7:30a * Chicago Marathon at Grant Park. |
| 7:00p Tributosaurus at Martyrs'. |
| Chicago Fire Anniversary. |
| Canadian Thanksgiving. |
| * Indigenous Peoples' Day at Parade (since 1953) at 12:30p. |
| International Film Fest at multiple theaters. |
| Farmer's Day. |
| 10:00a Reptile Breeders convention at Tinley Park (Sa+Su). |
| 10:00a * VeganMania at Broadway Armory. |
| 12:00p Music Box of Horror at Music Box Theatre. |
| 2:00p Model Rocket Launching at East Branch Forest Preserve. |
| Bosses Day. |
| 6:00p * Arts in the Dark Parade. |
| 7:30p Group Skate at Daley Plaza. |
| WAY too much great theater and comedy and dance to cover at Hundreds of city locations. |