On the shores of Lake Michigan, the ‘Windy City’ has something for everybody. A great destination at any time of the year, Chicago has a beautiful lakefront, breath-taking architecture, world-class shopping, wonderful museums, great theatres, gourmet restaurants and fantastic nightlife. Discover the delights of the Magnificent Mile, get a bird's eye view of the city from the 360 Chicago Observation Deck or from the Ledge at the Skydeck. If heights aren’t your thing take a stroll in Grant Park for a more relaxing option, visit the Shedd Aquarium, Navy Pier, take a boat tour or walk on the beach. Restaurants and nightlife abound throughout the city, with live music venues, theatres, world class restaurants and bars. 

Stay two nights in Chicago

 Leave Springfield and drive south along Route 66 toward St Louis. Along the way stop at the Ariston Café for great food and to look at the massive outdoor screens at the drive-in theatre in Litchfield. 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 Rover 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.

 Visit the Gateway Arch in the heart of downtown on the riverfront where the original Route 66 passed by. Enjoy one of the tastiest spots along the Mother Road at Ted Drewes Frozen Custard, and if that is not enough try the Donut Drive-In across the street, both Route 66 landmarks. This evening tour the music clubs of Leclade’s Landing and the Soulard neighbourhood and discover some of St Louis’ music history.

 Stay two nights in St Louis

Today you are heading for a second Springfield, this time in Missouri. Heading through the rolling hills of the Ozark Mountains, remnants of the old Route 66 are everywhere just of the Highway. A new addition to this is the Route 66 Neon Park in Saint Robert, showcasing nearly a dozen restored neon signs that once stood along the Missouri portion of the Mother Road. 

 The city of Springfield was the location, where in 1926, the name for the new trans-continental road was declared as Route 66. Much of the old highway frontage has been preserved along St Louis Street. Discover some of the stories surrounding Wild Bill Hickock and Jesse James in the surrounding area.

Stay one night in Springfield

You are heading into the South-west today as you cross into Oklahoma, so you will experience a change in scenery and in culture. With many Native Americans having been resettled here and the soil being suitable for cattle rearing, the area gave rise to the era of the American cowboy. 

Oklahoma City is the largest city in the state, and Bricktown - its renovated warehouse district - provides plenty of evening entertainment with over 30 canal-side restaurant and clubs. Visit the world class National Cowboy and Western Heritage Museum, the Oklahoma City National Memorial & Museum, the Red Earth Museum, FAM the First Americans Museum, the Myriad Botanical Gardens, the American Banjo Museum, the fast growing Boathouse District and the Paseo Arts District. Bustling Stockyard City is the home of America’s largest operating cattle auction, and you’ll find speciality merchants who offer superb Western apparel and supplies.

Stay one night in Oklahoma City.

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.

In Albuquerque historic neon signs still shine on Central Avenue and the other parts of Route 66 that cut right through the city. Discover some fantastic restaurants, unique shops and markets and a fascinating Spanish and Native American culture. A short drive away is Santa Fe, renowned for its Indian Pueblos and the spiritual and healing powers of its natural hot springs, warm dry climate and immense starry night skies. 

Stay two nights in Albuquerque

Today you will head across into Arizona, through Holbrook where a stop at the Petrified Forest National Park is well worth it, with its huge concentration of petrified wood and fossils dating back over 200 million years. 

In Flagstaff many of the old brick buildings in the downtown area are original to Route 66. Take a walking tour and discover more about these landmarks and finish in the Museum Club a historic roadhouse that still welcomes visitors to quench their thirst after a long day on the road. 

Stay one night in Flagstaff. Spend an extra night here if you want to see the Grand Canyon

There are a few sections of Route 66 that you can take from Flagstaff, including as you head west into California through the high Arizona desert from Seligman to Kingman. Then continue on to Barstow, where the Main Street is a section of Route 66. 

Barstow is home to Calico Ghost Town, a Silver Rush Ghost Town, parts of which are preserved as one of the few original mining camps in the Old West.

Stay one night in Barstow

 Continue on the last stretch of your ‘Main Street of America’ journey 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. 

Enjoy the beach, or the other sights of the Los Angeles area such as Hollywood, Beverly Hills, Universal Studios, Disneyland, or one of the museums representing the American West and Californian Heritage. Why not extend your holiday to include a bit more time to see the sights, or to relax.

Stay two nights in Santa Monica