Start Your Route 66 Road Trip in Chicago

Route 66, that iconic highway often associated with road trips through the wide-open American West, actually starts in a pretty unlikely place: Chicago. America’s most fabled highway, actually begins in Chicago at the corner of Jackson Boulevard and Michigan Avenue, from where it stretches West for 2,400 miles to Los Angeles.

If you’re thinking of ideas for summer road trips, consider starting from America’s most famous highway before traveling west. You can start your trip exploring one of the country’s biggest cities and then hit the open road, checking out the weirdest roadside attractions in America, stopping in small towns, or visiting the nation’s beautiful parks. The road originally ran through Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California, before ending at Los Angeles so you can visit cities like St. Louis, Amarillo, Oklahoma City, Tulsa, Albuquerque, and Flagstaff on this epic road trip.

See the Arch in St. Louis, try some New Mexico chile sauce in Albuquerque, visit the Grand Canyon from Flagstaff, or get lost in the smaller towns and tiny hamlets that line the historic road. When it comes to where to go in the US this summer for a road trip,  there are dozens of options from Chicago, but no drive better evokes the spirit of the open road than Route 66.  Even if you can’t commit to the whole drive, you can pick a section and explore before turning back, or fly to your starting point and get a one-way car rental that you can return in your home city. Either way, there’s no American road trip that compares to getting “your kicks on Route 66!”

Photo by Michael Kesler