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…

Lollapalooza Chicago things to do this weekend. July 31-August 2

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: 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…

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.

Summer Is Here: The Best Things To Do in Chicago May 29-31, 2026

This weekend in Chicago features perfect summer weather, with temperatures reaching 80 degrees and various events including three street festivals, the Windy City Hot Dog Fest, and Maifest, celebrating community and culture. Additionally, local pools and beaches are open, making it an ideal time to explore the city’s vibrant neighborhoods.

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…