Often called “The Mother Road”—a phrase popularized by John Steinbeck in The Grapes of Wrath—Route 66 begins in Chicago and runs to the Pacific Ocean, ending at the Santa Monica Pier. Few places capture its spirit as well as Illinois. Long sections of original roadway remain, offering one of the most authentic drives along the historic route.

Begin your road trip in the Windy City, a fabulous destination for food, culture and architecture. A slice of deep-dish at Lou Malnati’s Pizzeria, or a hearty breakfast at Lou Mitchell’s, an institution since 1923, sets the tone. Dining here is like a rite of passage before heading southwest.

As the skyline fades in the rear-view mirror, you may find yourself near the brooding Old Joliet Prison. Stark and cinematic with a nod to The Blues Brothers movie, the tourist attraction hints at Route 66’s grittier chapters.

Soon after, nostalgia flexes its muscle. The photogenic Gemini Giant, a fibreglass tribute to the Space Age, is a selfie-worthy local landmark, now anchored in Wilmington’s South Island Park.

In Pontiac, famous for its colourful public murals, stop at the Route 66 Hall of Fame Museum where you’ll walk through decades of road culture—each exhibit a breadcrumb of Americana.

In Atlanta, keep an eye out for giants—literal ones—at the American Giants Museum. Its supersized collection includes a towering Paul Bunyon statue. Then in Lincoln, there are more big sights, including the world’s largest covered wagon, the Railsplitter Covered Wagon.

When you reach Springfield, the journey shifts tone with kitsch giving way to history focused on Abraham Lincoln. The town is home to the U.S. president’s former home and the law office where Lincoln began his path to the presidency, and of course, his final resting place, the Lincoln Tomb.