Why Take a Route 66 Road Trip?

Few road trips capture the spirit of American travel quite like Route 66. Established in 1926 as part of the original US highway system, the route linked Chicago to Santa Monica and carried motorists across eight states and thousands of miles of varied American landscape. A century later, the Mother Road remains one of the country’s most famous drives, celebrated for its roadside attractions, historic towns, and the freedom of the open road. Vintage neon signs, restored diners, historic gas stations, and quirky landmarks still line surviving stretches of the highway, where every stop reveals another chapter of America’s road-trip tradition.

From big city to bigger country

The complete journey traditionally begins in Chicago, where the route’s eastern terminus places you in the middle of one of the country’s great cities before you gradually move west into smaller towns and wider landscapes.

A comfortable base for that first stage of the journey is the Cambria Hotel Chicago Loop, a modern downtown property that makes exploring the city easy before beginning your adventure. Its central location allows you to enjoy the urban energy of Chicago’s culture and dining scene while keeping the official starting point of Route 66 close at hand. Once you leave the city, the scenery changes quickly. Suburbs give way to farmland, historic alignments appear alongside newer highways, and classic roadside landmarks begin to pop up along the route.

The Midwest stretch and classic Americana

The Chicago to Oklahoma City portion of Route 66 is an especially accessible introduction to the Mother Road. This stretch crosses Illinois and Missouri before reaching Oklahoma, passing through towns where the culture of roadside travel still thrives. Along the way you’ll encounter historic bridges, vintage signage, and local diners that reflect decades of road-trip history. Many travelers stop in St. Louis, where the Gateway Arch marks a symbolic transition from the Midwest to the American West.

For an easy overnight nearby, Comfort Suites St. Louis – Sunset Hills provides a convenient location close to historic Route 66 alignments and major road corridors. Staying in properties positioned near the route keeps your itinerary flexible while allowing you to explore towns and attractions at your own pace.

From Missouri, the route continues into Oklahoma, where Route 66 culture remains deeply rooted. The state preserves long segments of the historic roadway and celebrates the highway through museums, restored landmarks, and local festivals.

A smart base here is Comfort Inn & Suites Oklahoma City West – I-40, located near one of the historic corridors that carried drivers across the state for decades. Stops like this make it easy to explore regional highlights while keeping the road trip moving comfortably westward.

Modern comfort for a century-old journey

While the spirit of Route 66 is rooted in history, modern travelers still want reliability and comfort along the way. Along with proper vehicle maintenance, having dependable accommodations at the end of long driving days can make or break your journey.

Choice Hotels properties are positioned in many of the cities and driving corridors you’ll encounter along the route, bringing consistency that helps you focus less on logistics and more on exploration. The variety of rooms and suites at Choice hotels also lends itself just as well to multi-generational traveling families as couples or solo trekkers.

AAA members gain additional advantages when staying along the way. Members can save 10 percent or more with AAA rates and earn Choice Privileges points at participating Choice Hotels locations — a considerable benefit when your journey includes several nights on the road.

A road trip designed for discovery

Part of what makes Route 66 endure is how adaptable its road trips are. You can drive the full Chicago-to-California route, or you can focus on shorter segments that fit into a weeklong getaway. Or even less.

The Chicago to Oklahoma City stretch is particularly appealing because it balances historic towns with manageable driving distances, and each day introduces something new. From restored neon signs and roadside museums in small towns to major monuments in key cities, Route 66 heritage is still celebrated throughout. The road unfolds gradually, carrying you from city streets into farmland and onward toward the wide landscapes of the American West as you create your own unique experience of the Mother Road’s charm. Few journeys offer such a clear connection between travel and history.

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A Route 66 road trip is more than a drive. It’s a chance to experience one of America’s most iconic highways, one town, landmark, and mile at a time.