Start your road trip with breakfast at Lou Mitchell's in downtown Chicago, a fixture on Route 66 since 1923. Then head to Jackson Boulevard at Lake Shore Drive, considered the official start of Route 66. Drive out to suburban Joliet and check out the Mother Road memorabilia at the Route 66 Welcome Center in the Joliet Area Historical Museum. Have lunch at Dell Rhea's Chicken Basket in Willowbrook, a Route 66 favorite since the 1940s. For dinner, enjoy elegant Old World cuisine at Barolo Ristorante, followed by a play or concert at Joliet's historic Rialto Square Theatre.

Head to Wilmington to see the famed Gemini Giant, a 28-foot-tall spaceman in front of the Launching Pad Drive-In. Be sure to motor over to the historically preserved Odell Station. Next stop is the Route 66 Association Hall of Fame & Museum in Pontiac, showcasing mementos from the Mother Road. Also check out the new Pontiac-Oakland Automobile Museum, featuring one of the world’s greatest collections of classic Pontiac and Oakland cars, along with dealer artifacts and a display of more than 2,000 antique oil cans. Have lunch at the Old Log Cabin Restaurant in Pontiac, which has been dishing up comfort food to Route 66 travelers since 1926. Pick up a sweet treat in Shirley at Funks Grove Pure Maple Sirup. And don’t forget a bite of the original corn dog for dinner at Springfield's nostalgic Cozy Dog Drive In.

Stop at Shea's Gas Station Museum in Springfield to hear stories about the Mother Road from owner Bill Shea, who has been doing business along Route 66 for more than 50 years. Have lunch in Litchfield at the Ariston Cafe, still decorated with its 1920s furnishings. Henry's Rabbit Ranch in Staunton celebrates Route 66 with memorabilia displayed in a replica vintage gas station. End your trip at the Old Chain of Rocks Bridge in Madison, built in 1929 to span the Mississippi River and now the largest pedestrian bridge in the world.