This driving tour will take you through some of the most iconic cities in Illinois, Wisconsin, and Minnesota as you explore some of the top attractions in Chicago, Milwaukee, Minneapolis, and beyond.
Day 1: Chicago
- Fly into Chicago O’Hare International Airport in (1) Chicago, Illinois
Points of interest: Some of America’s most notable museums can be found in Chicago, including the Art Institute of Chicago and the Field Museum, and neighboring Millennium Park’s star attractions are the Crown Fountain and Cloud Gate (aka “The Bean”)
Where to stay: Located on the Magnificent Mile, The Peninsula Chicago combines five-star Asian service with the cosmopolitan hospitality of Chicago; other luxury hotels include The Langham Chicago and the Four Seasons Hotel Chicago
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Day 2: Chicago-Milwaukee
- Drive to (2) Milwaukee, Wisconsin – 90 miles (145km); 1 hour, 30 minutes
Points of interest: Don’t miss the stunning Milwaukee Art Museum—one of the largest art museums in the U.S.—on Milwaukee’s lakefront, take a trip through motorcycle history at the Harley-Davidson Museum, or find delicious dishes and fun souvenirs at the indoor Milwaukee Public Market
Where to stay: Book a room at Milwaukee’s iconic (and some say haunted!) Pfister Hotel or plan a trendy stay at Saint Kate – The Arts Hotel
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Day 3: Milwaukee-Madison
- Drive to (3) Madison, Wisconsin – 80 miles (130km); 1 hour, 20 minutes
Points of interest: Madison is home to the University of Wisconsin’s flagship campus, and the university’s Memorial Union Terrace is a highlight in summer, as is the Dane County Farmer’s Market, and State Street is a pedestrian mall filled with restaurants and shops
Where to stay: The Edgewater is aptly named—it sits on the shores of Lake Mendota, just a short walk from the University of Wisconsin campus and the State Capitol
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Day 4: Madison-La Crosse
- Option 1: Drive to (4) La Crosse, Wisconsin – 145 miles (230 km); 2 hours, 15 minutes
Points of interest: Take a tour on the Mississippi River aboard the La Crosse Queen paddlewheeler, get inspired by the panoramic views of three states at Grandad Bluff, or visit the Dahl Auto Museum to see an impressive collection of classic cars
Where to stay: The Charmant Hotel is a boutique lodging property in a former candy factory two blocks from the Mississippi River, and the Castle La Crosse Bed & Breakfast offers outstanding lodging in an opulent 1890s home
- Option 2: Drive to (5) Wisconsin Dells, Wisconsin – 55 miles (90 km); 1 hour
Points of interest: Wisconsin Dells is known as the Waterpark Capital of the World® and is home to more than 20 indoor and outdoor waterparks, including Noah’s Ark Waterpark, the largest waterpark in America. Nature lovers can take a cruise along sandstone cliffs with Dells Boat Tours and visit attractions like Wisconsin Deer Park and the International Crane Foundation.
Where to stay:
- Drive from Wisconsin Dells to La Crosse – 90 miles (145km); 1 hour, 30 minutes
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Day 5: La Crosse-Minneapolis/St. Paul
- Explore the Minnesota Great River Road
- Drive to (6) Winona, Minnesota (30 miles/50km; 30 minutes)
- Drive to (7) Wabasha, Minnesota (30 miles/50km; 30 minutes)
- Drive to (8) Red Wing, Minnesota (30 miles/50km; 30 minutes)
Points of interest: Cross over the Mississippi and explore the cities and towns along the Minnesota Great River Road, including the Minnesota Marine Art Museum in Winona and Wabasha’s National Eagle Center, home to live eagle ambassadors and a great place to see eagles in the wild
- Drive to (9) Minneapolis, Minnesota – 55 miles (km); 1 hour, 15 minutes
The twin cities of Minneapolis and St. Paul (Minnesota’s capital city) offer a wide array of attractions for all interests, including the Walker Art Center and the Minneapolis Sculpture Garden, and outdoor attractions like Chain of Lakes Regional Park and Minnehaha Regional Park.
Where to stay: The Hotel Ivy is close to Minneapolis’ theater district, and the upscale Omni Viking Lakes Hotel is in Eagan, just south of St. Paul
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Day 6 – Minneapolis/St. Paul
Points of interest: A trip to the Twin Cities isn’t complete without a visit to the Mall of America (the largest shopping mall in the country, boasting more than 500 stores), and music fans can visit the home of a music legend at Prince’s Paisley Park in Chanhassen
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Day 7 – Minneapolis/St. Paul
Fly out of Minneapolis-St. Paul International Airport
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Points of Interest
(1) Chicago, Illinois
- Art Institute of Chicago: artic.edu
- Field Museum: fieldmuseum.org
- Millennium Park: millenniumparkfoundation.org
(2) Milwaukee, Wisconsin
- Milwaukee Art Museum: mam.org
- Harley-Davidson Museum: harley-davidson.com/us/en/museum.html
- Milwaukee Public Market: milwaukeepublicmarket.org
(3) Madison, Wisconsin
- Memorial Union Terrace: wisc.edu/visit/terrace-at-the-memorial-union/plan-your-terrace-visit
- Dane County Farmer’s Market: dcfm.org
- State Street: visitdowntownmadison.com
(4) La Crosse, Wisconsin
- La Crosse Queen: lacrossequeen.com
- Grandad Bluff: explorelacrosse.com/project/grandad-bluff-la-crosse
- Dahl Auto Museum: dahlautomuseum.com
(5) Wisconsin Dells, Wisconsin
- Noah’s Ark Waterpark: noahsarkwaterpark.com
- Dells Boat Tours: dellsboats.com
- Wisconsin Deer Park: wisdeerpark.com
- International Crane Foundation: savingcranes.org
(6)(7)(8) Minnesota Great River Road
- Minnesota Great River Road: mnmississippiriver.com
- Minnesota Marine Art Museum: mmam.org
- National Eagle Center: nationaleaglecenter.org
- Red Wing Shoe Store & Museum: redwingshoes.com/museum.html
(9) Minneapolis/St. Paul
- Walker Art Center & Minneapolis Sculpture Garden: walkerart.org
- Chain of Lakes Regional Park: minneapolisparks.org
- Minnehaha Regional Park: minneapolisparks.org
- Mall of America: mallofamerica.com
- Paisley Park: paisleypark.com
