| 10:00p Monday Night Ride at Lincoln Monument. |
| 6:00p Chi Hack Night at 1871. |
| 6:30p * Full Moon Fire Jam near lake south of Foster. |
| 6:30p Millennium Park Movies (Tu). |
| 9:00p Movieoke at Whistler. |
| 9:00p South Park new episode on COM. |
| UniverSoul Circus at Washington Park. |
| Halloween in the Parks. |
| National Taco Day. |
| World's Best Costume Shop at Fantasy HQ. |
| 5:45p Southside Critical Mass at Nichols Park Plaza. |
| 7:00p Scream Scene Haunted House Skokie (Fr/Sa). |
| Disclaimer. |
| 8:30a Perimeter Ride at Buckingham Fountain. |
| 9:00a Applefest at Lincoln Square. |
| 11:00a American Indian Pow Wow at DePaul campus. |
| 10:00p Madonnarama at Berlin. |
| 7:30a * Chicago Marathon at Grant Park. |
| 7:00p Tributosaurus at Martyrs'. |
| Chicago Fire Anniversary. |
| 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. |
| Canadian Thanksgiving. |
| * Indigenous Peoples' Day at Parade (since 1953) at 12:30p. |
| 11:00a Bloody Mary Fest at Theater on the Lake. |
| Bosses Day. |
| 10:00p Drum&Bass night at SmartBar. |
| Alaska Day. |
| 7:30p Group Skate at Daley Plaza. |
| Sweetest Day. |
| 6:00p * Arts in the Dark Parade. |
| 2:00p Model Rocket Launching at East Branch Forest Preserve. |
| 7:00p * Treehouse of Horrors XXIX on FOX. |
| Start of Scorpio. |
| United Nations Day. |
| World Origami Day. |
| 5:45p Critical Mass at Daley Plaza. |
| WAY too much great theater and comedy and dance to cover at Hundreds of city locations. |