Top 5 Things to Do in Chicago as a Looper
For many Loopers, Chicago is both a highlight and a turning point. After cruising up Lake Michigan, you’ll pass through this world-class city before beginning the inland rivers. It’s a big milestone—and also the perfect excuse to pause your journey and soak up some urban adventure.
Here are five things we loved (and think you will too) while visiting Chicago by boat:
1. Stroll the Magnificent Mile
Chicago’s famous stretch of Michigan Avenue is lined with shops, historic buildings, and plenty of people-watching. Even if shopping isn’t your thing, it’s fun just to take in the energy of the city as you wander this iconic strip.
2. Eat Deep-Dish Pizza
No trip to Chicago is complete without trying its signature dish. Whether you choose Giordano’s, Lou Malnati’s, or another local favorite, be prepared for cheesy, saucy, deep-dish perfection.
3. Explore Millennium Park
Right in the heart of downtown, Millennium Park is a must-see. Snap a photo at the reflective “Bean” sculpture, let the kids cool off at the splash fountains, or simply enjoy the green space surrounded by skyscrapers.
4. Visit the Museums
Chicago is home to some of the best museums in the country. The Field Museum (hello, Sue the T. rex) and the Art Institute of Chicago are both fantastic, depending on your interests and how much time you have.
5. Dive into the Shedd Aquarium
If you’re cruising the Great Loop, chances are you already love water. The Shedd Aquarium is a natural fit, with exhibits ranging from Caribbean coral reefs to beluga whales. It’s a great stop for families and adults alike.
Making the Most of Your Chicago Stop
Chicago is a big city, but don’t let that intimidate you. From the marinas along the lakefront, it’s surprisingly easy to get around, whether by bike, on foot, or with public transit. Give yourself at least a couple of days to explore; this is one stop on the Loop that deserves more than just a quick pass-through.
We’d Love to Hear From You!
Have you visited Chicago on your Loop or boating travels? Share your favorite must-dos in the comments—I’d love to hear what made your stop in the Windy City memorable!
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