Route 66 – The Mother Road.

There is no American road trip more iconic than Route 66, aka the “Mother Road,” a journey that gives travellers the true essence of a quintessential road trip. And it all starts in the incredible city of Chicago.  Route 66 runs the length of Illinois, connecting distinctive towns, local dining, scenic parks, and key heritage attractions. Here’s a selection of highlights along the route to help you build the perfect Illinois Route 66 itinerary:

No trip is complete without first spending time in one of the world's greatest cities – Chicago!.  With its impressive skyline set along the shores of Lake Michigan, Chicago offers a vibrant waterfront with beaches, marinas, and a bustling harbour district. The city’s location on one of the world’s largest freshwater lakes provides visitors with easy access to sailing, sightseeing cruises, and waterfront dining — a key highlight for first-time travellers. Treat yourself to unbelievable 360° views of the city and beyond at the Skydeck of Willis Tower-you can see up to four states on a clear day. Don’t miss dining at classic eateries like the Billy Goat Tavern or grab a slice of Chicago’s world-famous deep-dish pizza at Lou Malnati’s. You’ll probably wish you had more time in Chicago, but the road is calling. Snap a picture at the original Route 66 Begins sign on E. Adams St and get on your way!

As you leave Chicago behind and reach Joliet, visit the Old Joliet Prison, a castle-like prison built in the 1850s. It housed some infamous American criminals, but perhaps the bigger notoriety is for the prison’s role in American film and television, having been a filming location for both The Blues Brothers and Prison Break.

Your next stop will be Pontiac, where you’ll find a treasure trove of Route 66 nostalgia and a larger-than-life mural that makes the perfect photo backdrop. Spend the day exploring the Pontiac-Oakland Automobile Museum, where you will find a variety of classic and antique cars. Don’t forget to visit the Route 66 Hall of Fame Museum, home to thousands of artefacts and memorabilia associated with Route 66.

No trip through the Land of Lincoln would be complete without learning about Lincoln himself. Springfield, the capital of Illinois, is rich in American history and is home to several attractions dedicated to the nation's 16th president. Explore the Lincoln Home National Historic Site, where you can pay your respects at Lincoln’s Tomb – don’t forget to rub his shiny golden nose for good luck. For the most in-depth look into Lincoln’s life, visit the Abraham Lincoln Presidential Library and Museum. If you find yourself famished, head over to the Route 66 Motorheads Bar, Grill & Museum, where you can find some great eats.

The last part of your journey is packed with exciting stops that you won't want to miss, including The Original Historic Route 66 Brick Road, which was laid down in 1931 and gives travellers a peek into what the entire road used to look like before modern concrete roads. 

The ride down Illinois Route 66 is a journey through time, capturing the essence of America’s heartland. From the stunning lakefront of Chicago to the historic depths of Springfield, to all the unique, off-the-beaten-path attractions and landmarks, this iconic highway has many experiences that will make lasting memories.