Last Updated on March 26, 2024 by Laura

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This midwestern city set on the serene shores of Lake Michigan is chock full of great food and drink. Savor Milwaukee’s rich brewing history, paired with some of its most famous culinary delights—think craft beer, cheese curds, and brats. From there, the best road trips from Milwaukee can bring you to these other fabulous Midwest destinations.

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Fabulous Road Trips from Milwaukee


55 miles / 50 min.

In less than an hour from Milwaukee along I-94 W, you’ll find yourself in Madison, a vibrant university town and the state capital. It’s also an enticing destination for culture and recreation. Spend an evening at the Collins Recital Hall for a musical performance or meander through the Chazen Museum of Art before exploring the Allen Centennial Gardens. Our favorite spot for great views? Head to the observation deck atop the Capitol dome and enjoy 360-degree views of downtown. For outdoor fun, you can’t beat a cruise around Lake Mendota in a boat rental.

Chicago, Illinois

92 miles / 1.5 hrs.

To reach Chicago, drive about 90 minutes from Milwaukee along I-94 E. Chicago gives you a taste of big-city life, without the density, grime, or hurried pace of some other urban hotspots. The Windy City is known for its legendary skyscrapers, so check them out from the best seat in the house: an architecture boat cruise. Chicago is also a sports fan’s dream city, with major teams representing basketball, hockey, soccer and baseball. Baseball fans must make a pilgrimage to Wrigleyville, a neighborhood that buzzes with activity during Chicago Cubs home games. >> Recommended hotels in Chicago

Wisconsin Dells

123 miles / 2 hrs.

Sometimes a road trip’s best destination is an amusement park. That’s the case in the Wisconsin Dells, two hours along I-94 W from Milwaukee. For adrenaline junkies, the numerous theme parks and attractions include Noah’s Ark Water Park, Mt. Olympus Water and Theme Park, Tom Foolerys Adventure Park, and BigFoot Ropes Course. Get your fill of natural beauty at Mirror Lake State Park, where there’s a picturesque lake surrounded by sandstone bluffs and forest. You can camp, hike, or go swimming at the beach.

Door County

153 miles / 2.25 hrs.

One of the Midwest’s best-kept secrets, Door County—a peninsula that juts into Lake Michigan—has flown under the radar for many Americans. After just a two-and-a-half-hour drive from Milwaukee along I-43 N, you’ll find yourself in a place often compared to Cape Cod. There are dozens of charming villages and hamlets, 11 lighthouses, preserved natural areas, a flourishing farm-fresh dining scene, and a plethora of outdoor activities—all set along 300 miles of pretty shoreline. Although every town has its own personality, you’ll enjoy a beautiful and peaceful visit, wherever you go.

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337 miles/5 hrs.

In just five hours from Milwaukee along I-94 W, you’ll find yourself in one of America’s coolest cities: Minneapolis. One half of the Twin Cities, Minneapolis is known for its buzzing urban culture and its incredible natural attractions. This is the land of 10,000 Lakes, so—no surprise—a smattering of lakes dot the metropolis. Check out the Chain of Lakes, three interconnected bodies of water a few minutes southwest of downtown. Each is surrounded by walking and biking paths, with beautiful views of the city’s skyline. Summer is the ideal time to visit Minneapolis, when you can hit the beaches, hop in a kayak, or take in live music at an evening al fresco concert. Speaking of concerts, don’t miss a visit to First Avenue, the downtown club where Prince used to perform. For culture vultures, there’s nothing like the Walker Art Center and its iconic sculpture garden.