Chicago Greeter Riverwalk InstaGreeter Walk

If you’re looking for a fast, flexible Greeter experience, check out our Riverwalk InstaGreeter walks. These hour-long guided walks are a fun and informal way to get to know Chicago without having to register in advance. Discover public art, outdoor cafes, and scenic views along the bustling banks of the Chicago River. Meet a Greeter at the Vietnam Veterans Memorial on the Riverwalk.

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 →