Looking for the best things to do in Chicago this weekend? Halloween lands on a Saturday, clocks fall back Sunday, CPS is off Monday and Tuesday, and Tuesday is Election Day. Here is your guide to Northcenter Trick or Treat, Haunted Halsted and Día de Muertos in Pilsen.
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.
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 Labor Day weekend are as good as it gets. The Chicago Jazz Festival closes out its four-day run with a spectacular free finale at Millennium Park. Bike the Drive opens Lake Shore Drive exclusively to cyclists on Sunday morning for one of the most iconic Chicago experiences of the entire…
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 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…
Chicago fireworks 2026 season is here, and here is your quick hit list this for where to go and where to see them. This year is bigger than ever for America’s 250th birthday. So if you need a fast plan for the Fourth of July weekend, here is your quick hit list. We are covering…
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…