Looking for the best things to do in Chicago this weekend? You landed in the right place. This is one of those weekends where Chicago actually delivers. Free events, free architecture tours, a street festival on State Street, and Spooky Zoo at Lincoln Park Zoo, all happening Saturday and Sunday, October 16-18, 2026. I pulled…
Chicago Marathon weekend is one of my absolute favorite weekends of the entire year. The city is buzzing, strangers are cheering each other on, and there is something genuinely moving about watching 45,000 people run 26.2 miles through our streets. Whether you are running, cheering, or just soaking it all in with your kids on…
Chicago things to do this weekend officially welcome October and this city does fall better than almost anywhere. The Lincoln Square Ravenswood Apple Fest takes over one of Chicago’s most beloved North Side neighborhoods for three full days of apples, live music, arts and crafts and the crispest fall energy you will find anywhere in…
Chicago things to do this weekend span the full range of what makes this city impossible to leave. Riot Fest takes over Douglass Park in North Lawndale with one of the best punk and alternative lineups in the country, including Tool on Saturday night. Retro on Roscoe turns Roscoe Village’s beloved Roscoe Street into a…
Chicago things to do this weekend bring another great lineup as we head into the final stretch before Labor Day. The Chicago House Music Festival takes over Millennium Park and the Chicago Cultural Center all weekend long with free performances celebrating the music genre born right here in this city. Taste of Greektown fills Halsted…
Chicago things to do this weekend are genuinely some of the most fun options of the entire summer. The Savannah Bananas bring Banana Ball to Wrigley Field for three games, and yes, tickets are technically sold out but resale is available. Benson Boone’s Wanted Man Tour plays Allstate Arena in Rosemont both Friday and Saturday…
Chicago things to do this weekend cover every corner of the city and a solid range of neighborhood flavors. Roscoe Village crowns its best burger. West Town throws one of Chicago’s great house music street festivals. River North brings its best restaurants out to the street for two days. The Cubs host the Twins at…
Chicago things to do this weekend are running three of the best festivals of the entire summer simultaneously. Square Roots fills Lincoln Square with live music and local food. Taste of Chicago brings decades of tradition back to Grant Park with free live performances from Common, Babyface and Beach Bunny. Windy City Smokeout closes out…
Things to do in Chicago this weekend include one of the most historic moments our city has seen in years. The Obama Presidential Center officially opens to the public on Juneteenth weekend with free community celebrations across the South Side. Chicago Pride Fest celebrates its 25th anniversary in Northalsted. Taste of Randolph takes over the…
This weekend in Chicago, June 5-7, various festivals kick off the season, including Pokémon GO Fest at Grant Park, the free Chicago Blues Festival at Millennium Park, Ribfest in North Center, and the 57th Street Art Fair in Hyde Park. A real estate market update indicates changing buyer dynamics.