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Jack's Pumpkin Pop-Up event image
Goose Island, 1265 W. Le Moyne St., Downtown Chicago, Downtown, the Loop & West Loop

Jack's Pumpkin Pop-Up

Running through November 1 · See official site

Thousands of pumpkins, a downtown corn maze, games and food fill a Goose Island lot.

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Also that weekend in Downtown, the Loop & West Loop
Play On! — Chicago…F1 ArcadeHaunted by Our Dark Side…Chicago Bears vs. New York…Sun 12pm

Thousands of pumpkins, a downtown corn maze, games, and food fill a Goose Island lot.

Also in Downtown, the Loop & West Loop

Play On! — Chicago Shakespeare Theater
Play On! — Chicago Shakespeare TheaterSeptember 11–October 18, 2026; selected performancesThe Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopLimited Run
F1 Arcade
F1 ArcadeOpen this weekend — recently openedF1 Arcade, River North, Downtown, the Loop & West LoopLimited Run
Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime TourRuns through Oct 3, 2026Inside Chicago Walking Tours, Downtown, the Loop & West LoopLimited Run
Chicago Bears vs. New York Jets
Chicago Bears vs. New York JetsSun, Oct 4, 2026 · 12:00pmSoldier Field, Museum Campus, Downtown, the Loop & West LoopOne Day Only
Bill Burr Live
Bill Burr LiveFriday, October 2, 2026, 7:30 PM; Saturday, October 3, 7:00 PM and 10:00 PMThe Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopOne Weekend Only
See the full ranked weekend board →