Planning to get your kicks on Route 66 and join the festivities this year? Luckily, the 2,448-mile route boasts plenty of stylish stays along the way. Here are some of our favorites, from Chicago to Santa Monica.

Planning to get your kicks on Route 66 and join the festivities this year? Luckily, the 2,448-mile route boasts plenty of stylish stays along the way. Here are some of our favorites, from Chicago to Santa Monica.