Park, Tailgate, & Sail

Take the stress out of game day and make your trip to Soldier Field part of the fun! Join Harry Caray’s Navy Pier for Park, Tailgate & Sail, the ultimate pre-game experience for Chicago Bears fans. Start your game day with an all-you-can-eat tailgate buffet at Harry Caray’s Navy Pier, complete with drink specials from Sam Adams, Sun Cruiser Vodka Iced Tea, and Angry Orchard. Then, grab a Sun Cruis

Make a day of it

ACE IN THE HoleAfter · Sunday 4:15pmGene Siskel Film Center, the Loop, Downtown, the Loop & West LoopOne Day Only

Play On! — Chicago Shakespeare TheaterAnytime · September 11–October 18, 2026; selected performancesThe Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopLimited Run

Jack's Pumpkin Pop-UpAnytime · Running through November 1Goose Island, 1265 W. Le Moyne St., Downtown Chicago, Downtown, the Loop & West LoopLimited Run

More on Sunday →

Chicago Bears vs. New York JetsSun, Oct 4, 2026 · 12:00pmSoldier Field, Museum Campus, Downtown, the Loop & West LoopOne Day Only

Maxwell Street Market – season finaleSunday, October 4, 2026, 10am–3pmMaxwell Street between S. Halsted St. and S. Union Ave., Downtown, the Loop & West LoopFreeOne Day Only

ACE IN THE HoleSunday 4:15pmGene Siskel Film Center, the Loop, Downtown, the Loop & West LoopOne Day Only

World Music Festival Chicago: Global Peace PartySunday, October 4, 2026, noon–5pmHumboldt Park Fieldhouse (outdoor), Humboldt Park, Logan Square, Wicker Park & BucktownFreeOne Day Only

Also in Downtown, the Loop & West Loop

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 TourRuns through Oct 3, 2026Inside Chicago Walking Tours, Downtown, the Loop & West LoopLimited Run

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

The Chicks: Taking the Long WaySaturday, October 3 and Sunday, October 4, 2026, 8:30pmThe Auditorium, The Loop, Downtown, the Loop & West LoopTicketed via TicketmasterOne Weekend Only

Operation Mincemeat (Chicago)Friday, October 2, 7 p.m.; Saturday, October 3, 2 and 7:30 p.m.; Sunday, October 4, 1 and 6:30 p.m.CIBC Theatre, 18 West Monroe, Downtown, the Loop & West LoopOne Weekend Only

See the full ranked weekend board →