Best things to do in Chicago in October 2025: Pop-ups, markets, vintage finds & more

Popups & artist markets

• Jack’s Pumpkin Pop-Up — the maximalist fall experience: corn maze, 10,000+ pumpkins, photo ops, food, bars, games.
• Chicago Artisan Market — flagship curated market for local makers (fashion, home goods, food, art). In Fulton Market on October 19.
• Randolph Street Market — a hybrid of antiques, vintage, indie designer goods. The next one is October 5.
• Chicago Farmers Markets 2025 Schedule
  The City of Chicago maintains a list & schedule of farmers markets.

Citywide / seasonal events

• Lincoln Square Apple Fest — local fall fest with crafts, apples, food booths October 3-5.
• Chicago International Film Festival — check their official site for schedules & tickets. Running throughout October.
• Open House Chicago — when unusual buildings open up for tours, October 18-19.