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Shedd Aquarium
Route 66 Mural with a Pontiac car in front.

The Birthplace of the Road Trip

Arts, Culture & History

5 Days 371 Miles


Chicago, Joliet, Pontiac, Springfield, Great Rivers & Routes

Hit the mother road and all of her vintage glory

Route 66 Illinois Road Trip | 5-Day Itinerary

It's the things you see along the way that you remember most. The giant statue of the guy holding a hot dog. The drive-in where it’s not a day past 1955. The Lincoln monument. Legendary Route 66 begins in Illinois and offers road trippers 300 miles of vintage, quirky, and larger-than-life roadside attractions.

Day 1:


  • View looking down the Chicago river with Skyscrapers

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

Day 2:


  • Photo of the famous bean of Chicago.

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.

Day 3:

Joliet & Pontiac

  • Photo of the Gemini Gian holding a rocket.

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.

Day 4:


  • Exterior of the Lincoln home.

Meet Lincoln face to face

An Illinois road trip wouldn’t be complete without a dose of Honest Abe — you are in the Land of Lincoln, after all. If you’ve still got time on day 3, stop by the Lincoln Tomb when you arrive in Springfield. Be sure to rub his nose for good luck! Visit the Illinois State Capitol and Old State Capitol, and make time for the Abraham Lincoln Presidential Library & Museum — known for its variety of unique and interactive exhibits. When you’re ready for a break, stop by Route 66 Motorheads, a restaurant that doubles as a Route 66 museum.

Day 5:

Great Rivers & Routes

  • Motor bikers riding by the river

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.

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