This weeklong tour will take you on some iconic roadways—including the Great River Road and Route 66—as you travel through Minnesota, Wisconsin and Illinois.
Day 1: Minneapolis-St. Paul
- Fly into Minneapolis-St. Paul International Airport in (1) Minneapolis, Minnesota
Points of interest: The Twin Cities of Minneapolis and St. Paul are a haven for music and other live entertainment, including iconic venues like First Avenue and the Dakota Jazz Club, and visitors shouldn’t miss unique museums like the Walker Art Center and the Minneapolis Sculpture Garden, the Minneapolis Institute of Art, and the Mill City Museum
Where to stay: If you want a convenient place to stay when you’re exploring America’s biggest mall, the Radisson Blu Mall of America features 500 fashion-inspired guest rooms and suites just steps away from a shoppers’ paradise
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Day 2: Twin Cities to La Crosse
- Drive to (2) Red Wing, Minnesota – 50 miles (80km); 1 hour
Points of interest: Explore the Minnesota Great River Road as you head south out of the Twin Cities to Red Wing, home to Barn Bluff (which offers great views of the town and the river) and the Red Wing Shoe Store & Museum
- Drive to (3) Wabasha, Minnesota – 32 miles (50km); 40 minutes
Points of interest: At Wabasha’s National Eagle Center, visitors can learn about these amazing animals with help from live eagle ambassadors
- Drive to (4) La Crosse, Wisconsin – 72 miles (115km); 1 hour, 20 minutes
Points of interest: Explore the Mississippi River on an authentic paddlewheeler aboard the La Crosse Queen or enjoy the views and trails from atop Grandad Bluff, which overlooks three
states
Where to stay: Castle La Crosse Bed & Breakfast offers outstanding lodging in an opulent 1890s home
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Day 3: Wisconsin Great River Road to Galena
- Drive to (5) Prairie du Chien, Wisconsin – 60 miles (95km); 1 hour, 10 minutes
Points of interest: Discover the charming towns and cities along the Wisconsin Great River Road—in Prairie du Chien, spend an afternoon at Villa Louis Historic Site, which includes an 1871 restored Italianate-style mansion and several other historic buildings
- Drive to (6) Potosi, Wisconsin – 40 miles (65km); 50 minutes
Points of interest: Stop for a taste and a tour at the Potosi Brewery, which was originally founded in the area in 1852 and reopened on the old site in 2008; the site is also home to a brewpub and two museums
- Drive to (7) Galena, Illinois – 30 miles (50km); 40 minutes
Points of interest: Often voted as the best small town in America, Galena is a charming community in northwestern Illinois that’s home to a Main Street filled with shops and restaurants,
award-winning local businesses like Blaum Bros. Distilling Co., tours of the city with Galena Trolley Tours, and outdoor adventures at Chestnut Mountain Resort
Where to stay: Jail Hill Inn—a cozy place to stay situated in a former county jail building—has been named the best bed & breakfast in the country and the second-best worldwide
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Day 4: Illinois Great River Road
- Drive to (8) Moline, Illinois – 85 miles (135km); 1 hour, 45 minutes
Points of interest: Illinois’ and Iowa’s Quad Cities are home to famed agricultural manufacturer John Deere, and the John Deere Pavilion in Moline showcases the company’s tractors, construction equipment, and more with educational, interactive exhibits
- Drive to (9) Alton, Illinois – 210 miles (340km); 4 hours
Points of interest: The towns of Alton and Grafton in southwestern Illinois are home to rich opportunities to explore history, including the National Great Rivers Museum and the Lewis & Clark State Historic Site, and unique attractions like Mississippi Mud Pottery and Alton Stained Glass Works
Where to stay: The uniquely named Cracker Factory sits above Alton’s historic downtown, offering luxury accommodations with great views, and Tara Point Inn & Cottages in nearby Grafton is a scenic spot at the confluence of the Illinois and Mississippi Rivers
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Day 5: Alton to Chicago
- Drive to (10) Springfield, Illinois – 85 miles (135km); 1 hour, 30 minutes
Points of interest: Route 66 stretches from Illinois’ western border in Alton northeast to Springfield before eventually ending in Chicago—don’t miss attractions like the Pink Elephant Antique Mall in Livingston, Cozy Dog Drive In (the birthplace of the corn dog) in Springfield, the Illinois Route 66 Hall of Fame & Museum in Pontiac, and popular photo op the Gemini Giant in Wilmington
- Drive to (11) Chicago, Illinois – 200 miles (320km); 3 hours, 30 minutes
Points of interest: Museum lovers can explore the Art Institute of Chicago, the Field Museum, and the Museum of Science & Industry, and downtown’s Museum Campus also includes the Shedd Aquarium and the Adler Planetarium
Where to stay: Chicago is home to a wide array of luxury hotels, including the St. Regis Chicago, the Drake Hotel, the Ritz-Carlton Chicago, and the Viceroy Chicago
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Day 6: Chicago
Points of interest: Chicago’s Magnificent Mile is a world-renowned shopping district that’s home to upscale shops, restaurants, and hotels, and those interested in the history of the Second City’s iconic buildings can visit the Chicago Architecture Center and take a sightseeing cruise on the Chicago River
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Day 7: Chicago
- Fly out of O’Hare International Airport
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Points of Interest
(1) Minneapolis-St. Paul, Minnesota
- First Avenue: first-avenue.com
- Dakota Jazz Club: dakotacooks.com
- Walker Art Center & Minneapolis Sculpture Garden: walkerart.org
- Minneapolis Institute of Art: new.artsmia.org
- Mill City Museum: mnhs.org/millcity
(2)(3) Minnesota Great River Road
- Minnesota Great River Road: mnmississippiriver.com
- Barn Bluff: redwingmn.gov/343/He-Mni-Can-Barn-Bluff
- Red Wing Shoe Store & Museum: redwingshoes.com/museum.html
- National Eagle Center: nationaleaglecenter.org
(4)(5)(6) Wisconsin Great River Road
- Wisconsin Great River Road: wigrr.com
- La Crosse Queen: lacrossequeen.com
- Grandad Bluff: explorelacrosse.com/project/grandad-bluff-la-crosse
- Villa Louis Historic Site: villalouis.wisconsinhistory.org
- Potosi Brewery: potosibrewery.com
(7) Galena, Illinois
- Main Street Galena: enjoyillinois.com/explore/listing/galenas-main-street
- Blaum Bros. Distilling Co.: blaumbros.com
- Galena Trolley Tours: galenatrolleys.com
- Chestnut Mountain Resort: chestnutmtn.com
(8)(9) Illinois Great River Road
- John Deere Pavilion: about.deere.com/en-us/explore-john-deere/visit-us/john-deere-pavilion
- National Great Rivers Museum: mtrf.org
- Lewis & Clark State Historic Site: campdubois.com
- Mississippi Mud Pottery: mississippimudpottery.com
- Alton Stained Glass Works: altonartglass.com
(10) Route 66
- Pink Elephant Antique Mall: pinkelephantantiquemall.com
- Cozy Dog Drive In: cozydogdrivein.com
- Route 66 Association Hall of Fame & Museum: il66assoc.org
- Gemini Giant: enjoyillinois.com/explore/listing/gemini-giant
(11) Chicago, Illinois
- Art Institute of Chicago: artic.edu
- Field Museum: fieldmuseum.org
- Museum of Science & Industry: msichicago.org
- Shedd Aquarium: sheddaquarium.org
- Adler Planetarium: adlerplanetarium.org
- Magnificent Mile: themagnificentmile.com
- Chicago Architecture Center: architecture.org
