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Maxwell Street Market – season finale event image
Maxwell Street between S. Halsted St. and S. Union Ave., Downtown, the Loop & West Loop

Maxwell Street Market – season finale

Sunday, October 4, 2026, 10am–3pm · Free

Maxwell Street Market – season finale has enough weekend energy to earn a spot on the board.

← See all this weekend's Chicago picks
Also that weekend in Downtown, the Loop & West Loop
Play On! — Chicago…Jack's Pumpkin Pop-UpF1 ArcadeHaunted by Our Dark Side…
Free

Visitors to Maxwell Street will experience an eclectic mix of foods and finds—including handmade crafts, resale housewares, clothing, and much more.

Good to know

  • Where: Maxwell Street, Pilsen, West Town & the West Side.
  • When: 2026-10-04 10:00am.

Going? Keep it.

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
Jack's Pumpkin Pop-Up
Jack's Pumpkin Pop-UpRunning through November 1Goose Island, 1265 W. Le Moyne St., Downtown Chicago, 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
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

More free events

Fall Fest at Lincoln Park Zoo
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 2026
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 Festival
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
The Great Highwood Pumpkin Festival
The Great Highwood Pumpkin FestivalOctober 2–4, 2026; Friday 4–10pm, Saturday noon–10pm, Sunday noon–9pmDowntown Highwood, Highwood, Far SuburbsFree
Smart Museum Fall Exhibition Opening
Smart Museum Fall Exhibition OpeningSaturday, October 3, 2026, 2–5pmSmart Museum of Art, Hyde Park, Bronzeville & the South SideFree admissionArt
See the full ranked weekend board →

Common questions

When is it?

2026-10-04 10:00am

Where is it?

Maxwell Street, Pilsen, West Town & the West Side