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On this six-day, fly/drive journey, you'll travel legendary Route 66 from Chicago to St. Louis. It's the ultimate American road trip. Wind through small towns and back roads, and discover quirky landmarks from a bygone era. From small town diners to drive-in movie theatres, this is roadside America at its finest. Along this “Road of Dreams”, once synonymous with the great adventure of the open road, lie old-fashioned 1920's-1960's style petrol stations, drive-in restaurants and original antique signs. But it's not just the sights, it's the people and characters that make the road so unique.
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Day One: Chicago to Springfield (3 1/2 hours) Begin your first day with breakfast at legendary Lou Mitchell's in Chicago. Stop for some photos at the Gemini Giant/Launching Pad Drive-In in Wilmington, the Polka Dot Drive In in Braidwood, the Old Log Cabin Restaurant in Pontiac and some great old pretol stations. Check out the Dixie Truckers Home/Route 66 Hall of Fame. Overnight in Springfield. 
Day Two: Springfield Discover some of America's most significant historic sites in and around Springfield, the Illinois state capital: Lincoln Home National Historic Site, Old State Capitol State Historic Site, Lincoln's New Salem State Historic Site, the Dana-Thomas House by Frank Lloyd Wright and the Abraham Lincoln Presidential Museum/Union Station Visitor's Center. Have lunch at the Cozy Dog Drive In, home of the American original corn dog. Shea's Gas Station Museum is a favorite photo stop. Spend the night sampling the local music scene. Overnight in Springfield. 
Day Three: Springfield to St. Louis (1 1/2 hours) Depart Springfield and drive south along Route 66. At Chatham, the road on which you're driving is the original brick road laid by hand in 1932 and is on the National Register of Historic Places. Stop for a bite at the Ariston Cafe in Litchfield. Continue to the World Heritage Site of Cahokia Mounds, home to the largest prehistoric Indian civilization north of Mexico. Cross into Missouri and drive to the Old Chain of Rocks Bridge, the longest pedestrian bridge in the world, with stunning views of the Mississippi. In the heart of downtown St. Louis, the imposing Gateway Arch, America's tallest monument, is a must-see. Take a 630-foot ride to the top. Overnight in Southwestern Illinois. 
Day Four: St. Louis On of the tastiest spots along Route 66 is Ted Drewes Frozen Custard. They have been dishing out "concretes" since 1929. Just minutes away is the urban oasis of Forest Park. This historic green space houses the St. Louis Art Museum, St. Louis Zoo, St. Louis Science Center and Missouri History Museum– all free of charge. That night tour the music clubs of the Laclede's Landing and the Soulard neighborhood. Overnight in East St. Louis, Illinois at the Casino Queen and gaze at the St. Louis arch from your hotel room. 
Day Five: St. Louis to Galesburg, Illinois (3 1/2 hours) Day five takes you north to Hannibal, Missouri, boyhood home of author Mark Twain. Then it's back across the Mississippi River to Illinois. Head to Galesburg, home of American poet Carl Sandburg who immortalized Chicago as "The City of Big Shoulders." Stroll down Seminary Street Historic Commercial District to shop and dine. Overnight in Galesburg. 
Day Six: Galesburg to Chicago (3 hours) A quick interstate journey north finishes your loop back to Chicago. Those of you searching for adventure will find it at the International Route 66 Mother Road Festival in Springfield, held every September. This premiere annual event is attended by thousands of people from around the world and features hundreds of classic vehicles, live entertainment and celebrities, dozens of food booths, one-of-a kind exhibits, the world's largest sock hop, and more.
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