Things To Do
Architectural Boat Tour
Explore Chicago's iconic architecture in 60–90 minutes. You’ll cruise the Chicago River while someone who knows their stuff tells the stories behind the buildings.
The "Bean" & Millenium Park
Yes, it’s touristy. Also yes, it’s worth a quick stop. Millennium Park sits right off Michigan Avenue, and Cloud Gate (also known as the "Bean" is a Chicago classic plus it makes for fun photos. Make sure to walk around the surroundings and swing though Maggie Daley Park next door. The Art Institute of Chicago is a short walk away!
The Art Institute of Chicago
This is the 2nd largest art museum in the US – trailing just behind the Metropolitan Museum of Art in New York City. You'll find some iconic paintings, such as Georges Seurat’s "A Sunday on La Grande Jatte", Grant Wood’s "American Gothic", Edward Hopper’s "Nighthawks", and several paintings by Van Gogh and Monet.
Lakefront Trail
One of the best parts of Chicago is Lake Michigan. The Lakefront Trail runs for more than 29 km (18 miles), whether you want to walk, run, or rent a bike—this is a great way to enjoy great skyline views. You'll witness first hand how Chicagoans refuse to waste a single ray of sunshine after hibernating for 6 months.
Lincoln Park Zoo
Lincoln Park Zoo is great if you're looking for something easy and outdoorsy. Its free and it's a great spot to wander, you can pop in for 20 minutes or stay for a couple hours.
Lincoln Park & Lincoln Park Conservatory
Lincoln Park is our go‑to spot in the city—you can pretty much always find us wandering around here with Dixie. It’s actually Chicago’s largest and most-visited park, but you can still find quiet paths, ponds, and shaded corners. If you’re here on a Saturday morning, don’t miss the Green City Market, the neighborhood’s farmers market. It’s full of local produce, baked goods, flowers, and lots of dogs living their best lives. Just across the way is the Lincoln Park Conservatory, a historic glasshouse filled with tropical plants and seasonal floral displays. It’s free to visit, but you do need to reserve a time slot, and it’s a great little escape if you want to step into a warm, leafy oasis for a bit.