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…

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…

Unmask the Magic: Chicago’s Most Captivating Events

Chicago is buzzing with celebrations this Halloween weekend – and beyond! From spooky parades and pumpkin pop-ups to family-friendly museum events, there’s something for everyone to enjoy. Whether you’re dressing up for the Haunted Halsted Parade, exploring Jack’s Pumpkin Pop-Up, or taking the kids to the Peggy Notebaert Nature Museum for its Día de los Muertos…

Why Chicago in the Fall Just Hits Different🍂

If you’re trying to make the most of these last few crisp days before Halloween, Chicago’s got you covered – pumpkins, markets, and a few perfect excuses to wander around with a latte in hand. From family-friendly fall fests to local maker markets and open-street celebrations, the city’s weekend lineup is packed with cozy things…

Embrace the Magic: Chicago’s Most Captivating Family-Friendly Halloween Escapes

Looking for some festive, family-friendly fun in Chicago this weekend? Whether you’re in the mood for spooky science, glowing parades, architectural adventures, or costumed pups, the city has something for everyone. Here are four can’t-miss events happening October 17–19 that are perfect for kids, parents, and even pets! 🎃 BOO‑Palooza & BARK‑Palooza 2025 📍 Location:…

Fall Thrills in Chicago: Celebrate, Savor, and Soar This Weekend

Fall is in full swing in Chicago, and this weekend is packed with events you won’t want to miss! From celebrating Bavarian traditions at Oktoberfestiversary to catching a movie under the stars with Rooftop Cinema Club, enjoying seasonal fun at Fall Fest on the Riverwalk, or cheering on runners at the Bank of America Chicago…

Savor the Magic of Chicago: A Weekend of Apples, Wine, Food, and Art

🍂Chicago is buzzing with fall energy this weekend. The city has something for everyone. You can enjoy apple-cider doughnuts and small-town charm at the 38th Annual Lincoln Square Ravenswood Apple Fest. You can sip vintages at Lincoln Park Wine Fest or enjoy the festive atmosphere at St. Benedict’s Oktoberfest. Meanwhile, strolling through creative storefront galleries…