Chicago Greeter – Loop InstaGreeter

If you’re looking for a fast, flexible Greeter experience, check out our InstaGreeter walks. These hour-long guided walks are a fun and informal way to get to know Chicago without having to register in advance. You can find InstaGreeter walks year-round in the downtown Loop neighborhood and seasonally at the Chicago Riverwalk and select neighborhoods. Meet a Greeter at the Cultural Center (Randolp

Also in Downtown, the Loop & West Loop

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

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

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

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

More free events →

Fall Fest at Lincoln Park ZooSeptember 25–November 1, 2026; pumpkin patch open daily, live pumpkin carving weekends 10am–1pmLincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleFreeLimited Run

Lincoln Square Ravenswood Apple Fest 2026Through Oct 4, 2026; Friday 3–7pm, Saturday and Sunday 9am–6pmLincoln Avenue, Lawrence to Sunnyside, Lincoln Square, Andersonville, Uptown & Lincoln Square$5 suggested donation to enterFree

South Side Science FestivalSaturday, October 3, 2026, 9 a.m.–5 p.m.The University of Chicago, Hyde Park, Bronzeville & the South SideFreeOne 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

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

See the full ranked weekend board →