Best things to do in Chicago in October 2025: Pop-ups, markets, vintage finds & more
September 29, 2025
Popups & artist markets Citywide / seasonal events
Category
Popups & artist markets Citywide / seasonal events
Looking for more than just a latte or the latest Nora Roberts? Across Chicago, a growing number of bookstores, cafes and galleries are sharing bold ideas. Join a DIY workshop or sip coffee in a feminist bookstore…. Women & Children…
Chicago Shakespeare Theater’s free summer series, Shakes in the City, returns this season with a new take on A Midsummer Night’s Dream. This pop-up production brings Shakespeare’s dreamiest romantic comedy into neighborhood parks across Chicago from July 19-August 17, 2025….
Sure, the Art Institute and the Field are iconic, but what about a suburban museum dedicated to pinball machines? Or replica public housing apartments? Welcome to the quirky side of Chicago museums… Get zapped back in time at Galloping Ghost…
Dive deeper into Chicago’s vibrant art and architecture scene this summer during the exciting chicago architecture events. Check out open studios, walking tours, gallery openings and more. Architecture & design highlights Chicago Architecture Center (CAC) — Tours & programs Art,…
Whether you’re craving live theater, want to laugh at a comedy club, or feel like dancing in the park, Chicago is full of pay-what-you-can and low-cost options. Bookmark these for quick reference. Theater Steppenwolf Theatre – $20 for 20, pay-what-you-will…
