The Birthplace of the Road Trip

Let's hit the road

Your journey begins in Chicago. Book an architecture boat tour and enjoy the city from a new perspective, then refuel at a classic Chicago establishment like Billy Goat Tavern. For a relaxed afternoon, visit world-class attractions like the Chicago History Museum or the Museum of Science and Industry. 

Next, take in the city sights. 

Cloud Gate in Millennium Park (aka “The Bean”) is a must-see attraction for anyone visiting the city. To take things up a level, visit Skydeck Chicago or 360 Chicago for incredible views of the skyline.

When you’re ready to hit the road, be sure to snap the perfect selfie at the very spot Route 66 begins. You’ll find the iconic sign on E. Jackson Blvd.

Time for a pit stop

Your first stop is a tour at the Old Joliet Prison. Continuing on to Pontiac, pull over for a pic with the Muffler Man Gemini Giant, and then get ready for a dose of Route 66 memorabilia. Visit the Route 66 Mural & Hall of Fame Museum for an iconic photo op and get your classic car fix at the Pontiac-Oakland Automobile Museum.

End on a high note

Browse retro knick-knacks at the Pink Elephant Antique Mall (trust us, you won’t leave empty handed). Then move on to the world’s largest Catsup Bottle for a great roadside photo-op. In Collinsville, be sure to visit Cahokia Mounds State Historic Site for a great view. Chain of Rocks Bridge is another unique attraction nearby. For a bit of extra height, a Grafton Sky Tour offers spectacular aerial views with the added bonus of Aerie’s Winery waiting for you at the top.

And that completes your Illinois Route 66 road trip! This itinerary can easily be started in Chicago -- or flip the route if you are starting in southern Illinois.