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…
Things To Do in Chicago This Weekend: May 1-3, 2026
Things to do in Chicago this weekend are nothing short of spectacular as May finally arrives. First and foremost, welcome to the first weekend of the month that changes everything in this city. The weather is warm, the energy is up and Chicago is fully in its feelings about spring. This weekend we have a…
Things To Do in Chicago This Weekend: April 24-26, 2026
Things to do in Chicago this weekend are exactly what this city does best on a warm spring weekend. April 24 through 26 has a little bit of everything. There is a neighborhood race celebrating 30 years of community running, a Fire FC home game at Soldier Field with a giveaway, the biggest handmade shopping…
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…
Things To Do in Chicago This Weekend: March 6–8, 2026
CSO storytelling concerts, the last weekend on the Maggie Daley skating ribbon, Matisse opening weekend at the Art Institute, and a slow Saturday morning at Green City Market in Avondale. This is your Chicago weekend guide for March 6 to 8 and it is a good one.
Things to Do in Chicago This Weekend Including Super Bowl
Looking for things to do in Chicago this weekend that work for both families and adults, and still leave room for Super Bowl Sunday? I’ve got you covered. As a Chicago Realtor® and mom of pre-teens and teens, I know how tricky it can be to keep everyone entertained, especially on big weekends like the…
🎄 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.
Epic Things to Do in Chicago This Weekend: Immersive Exhibits, Thrilling Mystery Dinners, and Seasonal Magic
Looking for something fun to do in Chicago this weekend? Whether you’re into hands-on art, interactive theater, seasonal markets, or family-friendly exhibits, the city has something for everyone. Here’s a roundup of events you won’t want to miss. 🎨 Family Day at the Museum of Contemporary Art Chicago 📍 Location: 220 E Chicago Ave, Chicago, IL 60611 (near…
