Hit the Road for the 100th Anniversary of Route 66
Rediscover the First Miles of America’s Most Legendary Road Trip with Loews on 66
There’s something timeless about a summer road trip. The windows down, a playlist turned up, snacks in the passenger seat and the feeling that adventure is waiting just beyond the next exit.
For nearly 100 years, no road has captured that spirit more than Route 66.
Established in 1926, the “Mother Road” became the ultimate symbol of American travel, connecting Chicago to Santa Monica across more than 2,400 miles of diners, neon signs, roadside attractions and unforgettable small towns. As Route 66 celebrates its centennial, travelers are rediscovering the nostalgia, freedom and Americana that made the highway iconic in the first place.
And while many dream of driving the entire route someday, there’s a strong case to be made for the very first stretch from Chicago to St. Louis where the road trip culture of America truly begins.
The journey starts in downtown Chicago, at the iconic Navy Pier. From there, travelers head southwest through a string of classic Illinois Route 66 towns that feel frozen in time. Eventually, the road leads to St. Louis, where the Gateway Arch marks both a symbolic and literal gateway to the American West.
This summer, Loews on 66 is bringing new energy to this legendary stretch of highway with immersive experiences inspired by the nostalgia of the open road. Launching May 22 on National Road Trip Day (and just in time for Memorial Day Weekend and the unofficial kickoff to summer travel season) the program celebrates the first leg of Route 66 through curated stays, vintage-inspired dining experiences and family-friendly road trip moments across Loews Chicago Hotel, Loews Chicago O'Hare Hotel and Live! by Loews - St. Louis.
Guests can expect everything from nostalgic diner pop-ups to Route 66-themed suites, custom Rand McNally maps, road trip snack amenities and exclusive culinary collaborations inspired by classic Americana including an exclusive diner-esq ice cream flavor at the Museum of Ice Cream. At Loews Chicago Hotel, the ETA Pit Stop Café reimagines the classic roadside diner, while Live! by Loews – St. Louis debuts Route 66 at The Bullock, serving floats, retro-inspired eats and a signature Brown Butter with Bourbon Caramel ice cream created with Bold Spoon Creamery. Guests can also sleep in a diner inspired suite at Loews Chicago O'Hare.
More than anything, the Route 66 centennial feels like an invitation to slow down again and rediscover the joy of the journey. To stop for roadside pie, quirky attractions and small-town diners instead of rushing to the next destination. And with Loews Hotels anchoring each end, there’s no better way to start and end your trip.
