Experience the ‘Main Street of America’ on this fly-drive from Chicago to Santa Monica, including such highlights as the Chicago’s Magnificent Mile, the St Louis Arch, the Anheuser Busch Brewery, the Ozark Mountains, Native American culture, the Grand Canyon and the beautiful beaches of California. The ‘Mother Road’ as it was also known, no longer exists in its 2448 mile entirety, however our Route 66 Fly-drive takes in the stretches of the road that are still used today and are dotted with roadside cafes, motels and service stations, giving a true ‘Americana’ experience.
Day 1 - Arrive in Chicago.
Tower above the city’s world-famous skyline with admission to 360 Chicago (John Hancock Observatory). Ascend 94 stories to the observation deck of one of the tallest buildings in North America aboard its lightning-fast elevator. Then check out bird’s-eye views of landmarks like the famous Willis (Sears) Tower and the lakefront shoreline.
Stay for 2 nights in Chicago.
Day 3 - Chicago to Springfield, IL approx. 190 miles.
Before you embark on your road trip, fill up with breakfast at Lou Mitchell's legendary Route 66 café on Jackson Boulevard in Chicago. Meander past many delightful all-American haunts, including the Polka Dot Café, Dixie Truck Stop and Shea's Gas Station Museum. Stay overnight in Springfield.
Day 4 - Springfield to St Louis, MO, approx. 100 miles.
As you drive into Missouri you should make a stop at the Old Chain of Rocks Bridge - this original Route 66 span over the Mississippi River has been reopened as the world's longest pedestrian and biking bridge. The bridge offers a great view of the river and the downtown St Louis skyline. Stay overnight in St. Louis.
Whilst in St Louis visit the Gateway Arch in the heart of downtown where the original Route 66 passed by. Enjoy one of the tastiest spots along the Mother Road at Ted Drewes Frozen Custard, or the Donut Drive-In across the street, both Route 66 landmarks.
Day 6 - St Louis to Springfield, MO, approx. 220 miles.
Heading through the rolling hills of the Ozark Mountains, remnants of the old Route 66 are everywhere just off the highway. Much of the old highway frontage has been preserved along St Louis Street.
Stay overnight in Springfield.
Day 7 - Springfield to Oklahoma City, OK, approx. 280 miles.
As you head off onto your next stop, take a break in Baxter Springs. Explore the Decades of Wheels Museum, a tribute to beloved cars and motorcycles throughout history, located along Route 66 and dedicated to the preservation of this iconic highway’s history. Enjoy some well-earned road trip food at Rita’s Café on the Route and when you’re done munching be sure to head over to Rita’s Roost for some live music and decadent desserts. If you feel like an extra night stop before you get to Oklahoma City we suggest the Little Brick Inn in Baxter Springs as a delightful bed and breakfast.
Cross into Oklahoma and experience a change in scenery and culture. This is a cattle country and the area gave rise to the era of American cowboy.
Day 8 - Oklahoma City to Amarillo, TX, approx. 260 miles.
Overnight in Amarillo and make sure you take a drive along Amarillo Boulevard, the original Route 66, still dotted with 1950s motels that are so iconic of an American road-trip.
Day 9- Amarillo to Albuquerque, NM, approx. 285 miles.
The next state on your list is New Mexico, which still has the most miles of the original Route 66 that are driveable today. Even in its heyday, the number of roadside businesses that sprung up along the Mother Road here was exceptional and today in towns such as Tucumcari locals still cling on to as much of the original Americana as possible.
Day 11 - Albuquerque to Flagstaff, AZ, approx. 320 miles.
Head to Flagstaff, where are many of the old bricks buildings in the downtown area are original to Route 66. Be sure to visit the Museum Club a historic roadhouse that still welcomes visitors to quench their thirst after a long day on the road. Stay an extra night here if you want to take a day trip to the Grand Canyon.
Day 12 - Flagstaff to Barstow, CA, approx. 350 miles.
Route 66 continue from Flagstaff west into California through the high Arizona desert from Seligman to Kingman. Then drive on Barstow, where the Main Street is a section of Route 66.
Day 13 - Barstow to Santa Monica, CA, approx. 130 miles.
The last stretch of your 'Main Street of America' journey will take you to the California coast and Santa Monica, where Route 66 reaches the Pacific Ocean. Today Santa Monica is a haven for beach lovers with a boardwalk, pier, amusements, street performers, side walk cafes and bars and a true California atmosphere. Stay at the beach in Santa Monica for two nights.
Day 15
Head for the airport for your flight back to the UK.