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Milwaukee is just 1.5 hours from Chicago, making it an easy day trip filled with frozen custard, lakeside architecture, quirky museums, and Wisconsin’s famous cheese curds.
Kopp’s Frozen Custard
We kicked off our day at Kopp’s Frozen Custard, a Milwaukee institution loved for its creamy custards and oversized burgers. The daily flavors happened to be tiramisu and pralines n’ caramel—both silky smooth and just sweet enough.
Their jumbo cheeseburgers were piled high with cheese, fried onions, pickle relish, ketchup, and mustard. Messy, delicious, and completely satisfying, we finished every bite before the custard melted.
Basilica of Saint Josaphat
On the drive into the city, we stopped to admire the Basilica of Saint Josaphat. Completed in 1901 and built using salvaged materials from Chicago’s Federal Building, it’s one of the finest examples of Polish Cathedral-style architecture in the United States. Tours are available if you want to learn more about its history.
Milwaukee Art Museum
Downtown Milwaukee’s skyline is defined by the Milwaukee Art Museum, designed by Santiago Calatrava. Its dramatic “wings,” officially called the Burke Brise Soleil, open and close daily. Even though we visited on a Monday when the museum was closed, the building itself was worth the stop. Inside, the collection includes works by Monet, Picasso, and Georgia O’Keeffe.
Harley-Davidson Museum
Milwaukee is home to Harley-Davidson, and the museum tells the story of America’s most iconic motorcycle brand. Spread across 20 acres, the exhibits range from the company’s 1903 founding to famous movie bikes from Easy Rider and Terminator 2.
One of the most moving displays was a Harley that washed ashore in Canada after drifting across the Pacific Ocean following Japan’s 2011 earthquake and tsunami. With interactive displays and a full timeline of bikes, this museum fascinated both kids and adults in our family.
Milwaukee Public Market
For lunch, we stopped at the Milwaukee Public Market. It’s a lively indoor market filled with independent vendors offering everything from seafood and smoothies to spices and chocolate. We enjoyed fresh fruit smoothies, sampled local candies from Kehr’s, and browsed for edible souvenirs to take home.
Colectivo Coffee
Right across from the public market, we found Colectivo Coffee. With friendly staff, a cozy vibe, and excellent lattes, it was a perfect mid-afternoon break. The cafe is a local favorite and a great place to experience Milwaukee’s coffee culture.
Pabst Mansion
Next, we toured the Pabst Mansion, built in 1892 for brewing magnate Captain Frederick Pabst. The Gilded Age architecture has been beautifully restored, and the guided tours gave us a glimpse into Milwaukee’s history as one of America’s brewing capitals.
Cafe Hollander – Cheese Curds & More
Before heading back to Chicago, we had one final mission: cheese curds. Our barista at Colectivo pointed us to Cafe Hollander, where the deep-fried curds are made with Decatur Dairy Muenster cheese. They came out airy, crisp, and paired perfectly with a tangy sriracha ranch dip.
We also tried the garlic parmesan soft pretzel bites with warm bier cheese sauce. They were so good that we nearly ordered seconds. It was the perfect ending to our Milwaukee adventure.
How to Get to Milwaukee
By Air
The main airport serving Milwaukee is the Milwaukee Mitchell International Airport (MKE). Located just six miles south of downtown, it’s a convenient and easy-to-navigate airport.
By Train
Amtrak provides frequent and reliable train service to the Milwaukee Intermodal Station in downtown. The most popular route is the Hiawatha Service, which runs between Milwaukee and Chicago with multiple departures daily. This is a very popular and convenient option for travelers from Chicago and its suburbs.
By Car
Milwaukee is situated at the intersection of several major interstate highways, including I-94 and I-43. Approximate drive times from nearby cities are:
- From Chicago, IL: 1.5 hours
- From Madison, WI: 1.5 hours
- From Minneapolis, MN: 5 hours
The city’s downtown is very walkable, and public transportation, including the free Hop streetcar, is available to get around once you arrive. Having a car can be useful if you plan to explore the greater Milwaukee area.
Is Milwaukee Worth Visiting?
We think so. Milwaukee surprised us with its friendly vibe, family-friendly attractions, and fun food. From frozen custard and cheese curds to world-class museums and historic architecture, it’s an easy and rewarding day trip from Chicago. We left already talking about coming back to explore Madison and more of Wisconsin in the future.
More to Explore Nearby
If you have extra time in the region, consider adding these stops:
- Chicago – Just south, with world-class museums, food, and architecture.
- Lake Geneva – A charming lakeside town popular for boating and summer getaways.
- Madison – Wisconsin’s capital, known for its farmers’ market and lakeside bike trails.
- Kohler – A short drive north, home to spa resorts and a design center.
