U.S. Highway 66 — usually referred to simply as Route 66 — is one of, if not the, most iconic U.S. highways.
Stretching from Chicago all the way to California, Route 66 was also called the “Main Street of America” because it wound through small towns and was lined by restaurants, motels, gas stations, and tourist attractions in those towns. Then again, during the Great Depression, farm families who had been displaced from the Dust Bowl made their way west to California. In search of a better life, they followed what John Steinbeck called “The Mother Road” in his Pulitzer Prize-winning novel The Grapes of Wrath.
Route 66 was decommissioned as an official U.S. Highway in 1985 and was replaced by the Interstate system.
However, “federal and state agencies, private organizations, and numerous members of the public realized that remnants of the road were quickly disappearing, and that the remaining significant structures, features, and artifacts associated with the road should be preserved,” according to the National Park Service. In 1990, Congress passed Public Law 101-400, the Route 66 Study Act of 1990, which formally recognized that Route 66 “has become a symbol of the American people’s heritage of travel and their legacy of seeking a better life.”
The route is still traveled by people in search of the perfect road trip. One of the most famous legs of Route 66 is Chicago to St. Louis, which is fitting since the route does begin in downtown Chicago.
If you plan to make the trip, keep reading for some ideas to help create the perfect itinerary.
Start In Chicago
The sign designating the start of Route 66 is located at Adams and Michigan Avenue in downtown Chicago.
If you’ll be traveling from Chicago to St. Louis, you can start your trip at the Four Seasons Hotel in Chicago and end the road trip at the Four Seasons Hotel in St. Louis. In fact, if you’re staying at the Four Seasons in Chicago, you can even request a gourmet lunch-to-go from James Beard Award-winning chef Jonathon Sawyer of Adorn Restaurant and Bar at the Four Seasons Hotel Chicago.
You can learn more about the Four Seasons Hotel Chicago, including making reservations, here.
Stops Along Route 66
The Joliet Area Historical Museum And Route 66 Welcome Center
Plan to make a number of stops on your road trip; after all, that’s the whole point. You can begin at the Joliet Area Historical Museum and Route 66 Welcome Center for maps and information.
The Old Joliet Prison
Your next stop in Joliet should be the Old Joliet Prison, formerly known as Illinois State Penitentiary. Parts of numerous movies were filmed at the prison, including The Blues Brothers, Natural Born Killers, and Stir of Echoes.
You can learn more about taking self-guided tours of the prison and find ticket information here.
Gemini Giant Statue
When you get to Wilmington, Illinois, you’ll want to stop at the Launching Pad Restaurant. You may even want to have your picture taken with the Gemini Giant in front of the restaurant. The 28-foot-tall statue was named after NASA’s Gemini space missions.
Route 66 Hall Of Fame
If you’re motoring west on Route 66, your next stop should be the Illinois Route 66 Hall of Fame and Museum in Pontiac, Illinois. Here’s why: The bricks in front of the large Route 66 mural are original Route 66 bricks. You can even park your vehicle on the bricks in front of the mural for a photo.
Abraham Lincoln Presidential Library And Museum
Illinois is the “Land of Lincoln,” so be sure to make a stop at the Abraham Lincoln Presidential Library and Museum in Springfield. The museum features immersive displays, so you may see actors in costume at exhibits, listen to a Civil War-era band, and even talk to characters and storytellers.
You can learn about buying tickets for the Abraham Lincoln Presidential Library and Museum here.
Abraham Lincoln’s Home
While you’re in Springfield, be sure to also stop at Abraham Lincoln’s Home, a national historic site.
There is no fee to tour Lincoln’s House, but keep in mind that tickets are issued on a first-come, first-served basis. You can learn about tickets and passes here.
Cozy Dog Drive In
The Cozy Dog Drive In, also in Springfield, has been serving the “Original” hot dog on a stick, which has been dipped in batter and deep fried, for more than 70 years – just don’t call it a “corn dog.”
You can find the hours of operation here.
Litchfield Skyview Drive-In
The SkyView Drive-In Theater in Litchfield, Illinois, is one of only four remaining drive-in theaters along Route 66, and it’s the only one in Illinois. The theater, which is preparing its 72nd season of showing movies, opens April 1.
You can find a schedule of upcoming screenings, along with their original trailers, here.
Chain Of Rocks Bridge
Sitting 60 feet above the Mississippi River, the Chain of Rocks Bridge in Madison, Illinois, gets its name from a nearby 17-mile stretch of rocky rapids north of St. Louis. Movie aficionados take note: Film director John Carpenter used Chain of Rocks Bridge as a setting in his 1981 movie Escape from New York.
Gateway Arch National Park
A road trip to St. Louis won’t be complete without a stop at Gateway Arch National Park, home to both the world-famous Gateway Arch and St. Louis’ Old Courthouse. The 630-foot-tall Gateway Arch took 2 years to build and was finished in 1965.
You can find tips for planning a visit to Gateway Arch here.
Other Stops Along The Way
There are, of course, numerous other stops you can make along Route 66 from Chicago on your way to St. Louis. For example, you can also make time to visit the Art Institute of Chicago, the historic Rialto Square Theatre in Joliet, and the historic Standard Oil Gas Station in Odell, Illinois, which was the first standard oil gas station in Illinois.
Finish In St. Louis
You can finish your road trip with a night or two at the Four Seasons Hotel St. Louis, which happens to be a short walk from the landmark Gateway Arch.
What’s more, if you prefer to start your road trip in St. Louis and end in Chicago, that’s possible too — you’ll just need to reverse the order of the itinerary above. Plus, if you’re staying at the Four Seasons Hotel St. Louis, you can even get a gourmet lunch-to-go from James Beard Award-winning chef Gerard Craft of Cinder House Restaurant at Four Seasons Hotel St. Louis.
You can learn more about the Four Seasons Hotel St. Louis, including making reservations, here.
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