Passing a colossal cross section of the United States, Route 66 offers the chance to soak up some of the country’s most iconic scenes. Of course you won’t be able to see every city on your Route 66 trip, but there are some you should be careful not to miss.

Chicago, Illinois

Chicago, the cradle of contemporary architecture, is where it all begins for Route 66. Catch the Cubs at Wrigley Field, take in one of the world’s most compelling skylines at the Willis Tower’s Sky Deck (the tallest building in the Western Hemisphere) before tucking into a deep dish pizza at Lou Malnati’s – known for its trademark buttery crust.

Something of must-see in its own right, a visit to Chicago shouldn’t be without a walk around the city’s famous Millennium Park. It’s here that the city’s Cloud Gate (better-known as ‘The Bean’) calls home, while it also plays host to a number of concerts and festivals throughout the year.

St. Louis, Missouri

As you pass into Missouri, take a quick detour through St. Louis. Although it’s the largest city along your Route 66 trip, you’ll find the ‘Gateway to the West’ is surprisingly provincial. Once an outpost for the French Republic, the famous city was founded on a river between Missouri and Illinois, and has its prominent portside location to thank for of its quintessential character.

With steamers gliding north and south, the city is permeated with wonderful blend of Midwestern charm and Southern drawl, and as such, the food in St. Louis is unique, and delicious. Discover slingers – St Louis’ breakfast of choice that features protein topped with eggs, hash browns, chili and cheese at one of the city’s many diners – before catching a baseball game at Busch Stadium.

Tulsa, Oklahoma

Situated atop the world’s largest known oil reserve, Tulsa, Oklahoma’s second-largest city, is built on black gold. The money made from this discovery can be seen in its beautiful architecture – with museums, churches, even gas stations all rendered in decorative, decadent style.

The locally-named downtown Deco District is the best place to seek out the many representations of this distinctive architecture movement in one place — namely the Atlas Life building, Tulsa Club, and the Philtower building. The internationally-acclaimed Gilcrease Museum, home to the world’s largest collection of art and artefacts of the American West, is well worth a visit.

Santa Fe, New Mexico

Towards the tail end of your Route 66 trip, you’ll come across one of America’s oldest cities – Santa Fe, found beneath the lofty Sangre de Cristo Mountains. A dreamy patchwork of Native American, Spanish and Mexican influence, the centuries-old Plaza remains as the city’s centre of activity – just as it was over 400 years ago.

Explore ancient Anasazai ruins at the Bandelier National Park, catch some culture at the Georgia O’Keeffe Museum or take in the views of the Jemez mountains, which is also home to Valles Caldera – a 2-million-year-old volcano.

Santa Monica, California

Framed by beaches on one side and mountains on the other, Santa Monica is a sanctuary that’s carved into the Pacific coastline. It’s here that Route 66 meets its end at the city’s pier, a classic, double-jointed boardwalk which hosts an ephemera of outdoor film and music events throughout the year.

Head to Camera Obscura, an old optical contraption offering off-kilter ocean views, before people-watching at the original Muscle Beach – birthplace of America’s fitness boom in the early 20th Century.

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