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…
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…
Not traveling for spring break? Good. Your Chicago spring break staycation is going to be better than wherever everyone else is going. This weekend marks the first full weekend of spring. Moreover, this city is showing up for it in a big way. We have flowers, a 30,000-person race through the Loop, an immersive David…
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…
Looking for fun things to do with kids this weekend in Chicago? Whether you’re planning a family outing or seeking adult-friendly events, the city offers a plethora of activities to make your weekend memorable. Here are some top picks for both adults and kids happening this weekend, May 30–June 1, 2025. 🎉 Family-Friendly Events 1.…
As the city blooms into Spring, Chicago offers a plethora of activities for both adults and children. Whether you’re planning a date night or a family outing, here are some top picks to make the most of May this weekend! 1. Titanique: A Musical Parody Experience a hilarious twist on the classic Titanic tale with “Titanique,” a…
To tag onto my ‘where to raise your family in Chicago’ post, this week we are featuring Lakeview. Lakeview encompasses so many amazing neighborhoods including West Lakeview, Southport Corridor, East Lakeview, Boystown, Wrigleyvile and even bits of Buena Park are all considered to be Lakeview as a whole. The medium price point for single family…