Arts in the Dark | Columbus Dr | October 24

Adler at Night | Adler Planetarium | October 21

Lincoln Square Greektober Fest | St. Demetrios Church | October 17-18

Crush Fest | Vin312 Winery | October 17

Night of 1,000 Jack-o’-Lanterns | Chicago Botanic Garden | October 7 - 11

Fall Fest | Lincoln Park Zoo | September 25 - November 1

Lincoln Square Ravenswood Apple Fest | N. Lincoln Ave | October 2-4

Hyde Park Jazz Festival | Citywide | September 26 - 27

Chicago Gourmet 2026 | Millenium Park | September 24 - 27