Highways and History of the Midwest: Chicago & the Upper Midwest
Itinerary - Highways and History of the Midwest:
Chicago & the Upper Midwest
Regional Suggestions Chicago | Route 66 | Indianapolis
Ohio Three-City Tour | Detroit

About this itinerary

Driving distance: 790 Miles
Recommended travelling time: 16 Days
Recommended travel season: Spring, Summer or Autumn
Chicago, Illinois, the cultural heart and soul of the Midwest, is the perfect starting point to launch a Midwest adventure. Savour the city's many charms, then travel down iconic Route 66, see racing cars at the Indianapolis Motor Speedway, learn about automotive history and Motown music in Detroit, and enjoy the natural splendour of Michigan.

Chicago, Illinois


Start with a visit to some of Chicago's iconic attractions such as the Cloud Gate sculpture at Millennium Park, the Sky Ledge glass balcony off the 103rd floor of Willis Tower and the new Centennial Ferris Wheel at Navy Pier. Alternatively visit one of the many museums. In the evening drop in on one of Chicago's many music venues or try some of Chicago's local beer and a hot dog.
To next stop: 203 miles| Total distance travelled: 0 miles


Route 66, Illinois

From Chicago, hop on historic Route 66 for a true slice of Americana. The famous road covers 300 miles in Illinois and is dotted with homey cafés, quirky shops and unique roadside architecture and artwork. Snap a photo in front of the towering Railsplitter Covered Wagon in Lincoln or the huge pink elephant near the Pink Elephant Antique Mall in Livingston. Drive south to delve into Abraham Lincoln's life in Springfield.
To next stop: 212 miles | Total distance travelled: 203 miles

Indianapolis, Indiana

The Indianapolis Motor Speedway, home of the Indianapolis 500, is known as 'the racing capital of the world'. The racetrack is also home to the Indianapolis Motor Speedway Museum, packed with racing memorabilia and automobiles from many racing series and also offers laps of the track. Next, slow down with a trip to South Bend (three hours north) to tour the stately campus of the University of Notre Dame.
To next stop: 112 miles | Total distance travelled: 415 miles


Ohio Three-City Tour, Ohio

See the sights in Ohio's three largest cities. Start at the top of the state in Cleveland and head to the Rock and Roll Hall of Fame and Museum to see historic memorabilia. In Columbus, the state's capital in central Ohio, don't miss the recently renovated Columbus Museum of Art or one of the city's many breweries. Drive southwest to Cincinnati and make sure to visit the Cincinnati Zoo.
To next stop: 263 miles | Total distance travelled: 527 miles

Detroit, Michigan

Start in urban Detroit, the birthplace of the USA's obsession with automobiles. The Henry Ford Museum and the Ford Rouge Factory Tour in nearby Dearborn are both highlights. The Motown Museum explores the history of this uniquely American musical genre. Take a break from city life with a trip to Michigan's natural wonders. Hike sandy beaches and towering bluffs or take a boat tour to see the towering sandstone cliffs of Pictured Rocks National Lakeshore before heading back into the city for your flight out of Detroit.
Total distance travelled: 790 miles

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Some map icons by Scott de Jonge, used under CC 3.0 BY  Train vecotr by Freepik

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