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…
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…
Chicago Things to Do this Weekend: Market Days, & August in Real Estate
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: Savannah Bananas, Benson Boone and Wicker Park Fest
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…
Chicago Things To Do This Weekend: Burger Fest, West Fest and What’s Happening in the Market Now
Chicago things to do this weekend cover every corner of the city and a solid range of neighborhood flavors. Roscoe Village crowns its best burger. West Town throws one of Chicago’s great house music street festivals. River North brings its best restaurants out to the street for two days. The Cubs host the Twins at…
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…
Crosstown Classic, Mayfest and Teen Birthday Ideas: Things to Do in Chicago this Weekend May 15-17
Things to do in Chicago this weekend include some of my favorite things about this city all landing at once. The Crosstown Classic is here and yes, the whole city has picked a side. Lincoln Park Mayfest finally kicks off after we teased it last week. Renegade Craft Fair takes over Andersonville. And I have a…
Bagels, Donuts, Brunch and a Summer Full of Festivals: Things to Do in Chicago May 8-10, 2026
Things to do in Chicago this weekend are especially delicious this May, and this one happens to fall on Mother’s Day weekend. First and foremost, we are devoting a full section to a Lincoln Park food crawl in two parts. Part 1 is a Saturday morning with the whole family. Part 2 is a Sunday…
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…
Chicago Spring Break Staycation Guide: March 20-23, 2026
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…
