Chicago Things To Do This Weekend: Riot Fest, Retro on Roscoe, Old Town Oktoberfest, the Race to Wrigley and Bears Home Opener

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…

Ultimate Chicago Weekend: Taco Fest, Thirsty Ears, Fall Market

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…

Things To Do in Chicago this Weekend: Pride, Porchfest and a Real Estate Win

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: Obama Center Opens, Pride Fest turns 25, and We Made the WSJ/RealTrends List

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…

June in Chicago: Blues Fest, Pokémon GO Fest and a Real Estate Market Update

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.

Magic, Art and the Lakefront: Best Things To Do in Chicago April 10-12

Things to do in Chicago this weekend are plentiful, and it feels genuinely good to be back. Life pulled me away from the blog for the past two weeks in the best possible way. Our youngest turned 10, which meant birthday celebrations took full priority. Also, public and private school spring breaks do not always…

photos with santa

🎄 Things to Do in Chicago 🎅 Holiday Edition! Where to See Santa in Chicago

Find the best places to see Santa in Chicago. Discover four festive locations with photos, hours, what to expect and nearby holiday activities.

Family Fun in Chicago This Weekend (Nov 15-16, 2025)

Chicago families can enjoy four events this weekend, November 15-16, 2025. Highlights include the Lycée French Market for artisanal shopping, the Illumination tree walk at Morton Arboretum, the Frankie Knuckles Festival for music and arts, and ZooLights at Lincoln Park Zoo, featuring festive lights and activities for all ages.

✨ Make the Most of Your Weekend: 4 Amazing Chicago Events (July 18–20)

Looking for fun things to do in Chicago this weekend, July 18–20, 2025? Whether you’re planning a night out or a family day with the kids, the city has something exciting for everyone. From lively street festivals and live music to free outdoor workouts in Millennium Park, this list highlights four top events you can…

✨Can’t-Miss Things to Do in Chicago This Weekend (July 11–13)

Looking for exciting things to do in Chicago this weekend July 11–13, 2025? Whether you’re spending time with the kids or planning a fun night out, Chicago has something for everyone. From cultural festivals to candlelit concerts and food trucks galore, this list has your perfect weekend covered. Keep reading for four top events you…