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…
PUBLISHED SEPTEMBER 25, 2026 · BY RAISING KIDS IN CHICAGO Chicago things to do this weekend prove that fall in this city is every bit as good as summer. Chicago Gourmet closes out its four-day run at Millennium Park with world-class chefs, wine and spirits tastings and the best food event of the fall season.…
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 feel like the city’s final bow before fall takes over. Private schools open August 20 and CPS follows August 24. This means it is genuinely the last full weekend of summer for most Chicago families. The 13th annual Lakeview Taco Fest takes over the Southport Corridor all weekend. It…
Chicago things to do this weekend prove that even in the height of the summer slowdown, this city never actually slows down. Northalsted Market Days is one of the largest LGBTQ+ street festivals in the country and it takes over Halsted Street all weekend long. Ginza Holiday brings a beautiful Japanese cultural celebration to Old…
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…
Juliana Yeager Lakeview East Festival of the Arts Explore artwork from over 150 juried artists at this annual event in Lakeview East, where live music adds to the atmosphere. When hunger strikes, check out the many food and drink booths, or bring the kids to the Kidzone for origami demonstrations, circus acts, live music, and…