The Tamesis
Nothing embodies the spirit of freedom, adventure and independence more than Route 66, which has captured the imagination of road travelers and romantics around the world.
The Mother Road is known for its unique Americana vibe, featuring neon-lit motels, retro signage, and old-school restaurants. However, it passes through eight states and some of the most stunning scenery in the United States
This year, America’s iconic highway will celebrate its 100th anniversary with events, festivals, concerts and art installations, such as the National Centennial Commemoration in Springfield, Missouri (April 29-May 3, 2026) and the Route 66 Highway Festival in Tulsa, Oklahoma (June 27-28, 2026).
Planning on having fun and joining in the festivities on Route 66 this year? Luckily, there are plenty of stylish accommodations along the 2,448-mile route. Here are some of our favorite spots, from Chicago to Santa Monica.
Chicago Athletic Association
Chicago, Illinois
Photo: Courtesy of Chicago Athletic Association
Turn-of-the-century male politicians and leaders owe their arrogance to this architecturally striking hotel, filled with intricate woodwork, arched windows and mosaic tile floors. Inspired by the Doge’s Palace in Venice and designed in Venetian Gothic style, the Chicago Athletic Association opened in 1893 as a private club for the city’s top leaders. It remained open to members only until 2007, the same year it was placed on Chicago’s Endangered Buildings list, and was converted into a 240-room hotel in 2015 (part of the Hyatt Unlimited chain). The rooms tell the story of the hotel’s history, with many featuring fireplaces, wrought-iron bathtubs and original stained glass accents. There is also an 8-seat omakase bar, a popular rooftop bar with views of Millennium Park and Lake Michigan, a game room, an indoor golf simulator and a gym. It was awarded a Michelin key.
21c Museum Hotel St. Louis
st louis missouri
Photo: Courtesy of 21c Museum Hotel St. Louis
