Few things encapsulate the spirit of freedom, adventure, and independence more than Route 66, which has seized the imaginations of road trippers and romantics around the world.
The Mother Road is known for its distinctly Americana vibe, characterized by neon-lit motels, retro signage, and old-school diners. But, cutting through eight states, it also passes some of the most stunning scenery in the U.S.
This year, the iconic American highway is celebrating its 100th anniversary with events, festivals, concerts, and art installations such as the Centennial National Kick-Off in Springfield, Missouri (April 29 to May 3, 2026), and the Route 66 Road Fest in Tulsa, Oklahoma (June 27 to 28, 2026).
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.
Chicago Athletic Association
Chicago, Illinois
Photo: Courtesy of Chicago Athletic Association
The hubris of male politicians and leaders at the turn of the century is to thank for this architecturally striking hotel filled with intricate woodwork, arched windows, and mosaic-tiled floors. Inspired by the Doge’s Palace in Venice and designed in the Venetian Gothic style, Chicago Athletic Association opened in 1893 as a private club for the city’s head honchos. It remained members-only until 2007, was added to Chicago’s endangered buildings list that same year, and was turned into a 240-room hotel (part of The Unbound Collection by Hyatt) in 2015. Rooms hearken back to the hotel’s history, many with fireplaces, wrought-iron bathtubs, and original stained glass accents. There’s also an eight-seat omakase counter, a popular rooftop bar with views of Millennium Park and Lake Michigan, a game room, indoor golf simulators, and a gym. It’s been awarded one Michelin Key.
21c Museum Hotel St Louis
St. Louis, Missouri
Photo: Courtesy of 21c Museum Hotel St Louis