Looking for the best things to do in Chicago this weekend? It is the weekend before Halloween and the city goes all in: two days of Lincoln Park Spooktacular, Lincoln Scared in Lincoln Square, the Arts in the Dark parade and Trick or Treat on Southport on Monday.
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 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 are headlined by one of the most iconic music festivals in the world. Lollapalooza takes over Grant Park for its final weekend with Charli XCX and The Smashing Pumpkins on Friday, Olivia Dean and JENNIE on Saturday and Doja Cat closing the whole thing out Sunday night. For the…
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…
Things to do in Chicago this weekend cover almost every corner of this city. The 55th annual Chicago Pride Parade marches through Northalsted on Sunday and is expected to draw more than a million spectators. Logan Square Arts Festival fills the neighborhood with artists, food and live music all weekend. Roscoe Village turns its front…
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…