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Route 66 Fly Drive Holidays

What better way to experience America than by hitting the open road and cruising along Route 66! We can tailor make your Route 66 holiday to suit your budget and your needs and we have listed some of the must stop cities and towns below to help get you on your way!


Chicago is the starting point for all Route 66 fly drive holidays.This bustling city is full of amazing restaurants, shopping and more! The history of Chicago and Illinois comes alive when you take the Chicago Architecture Foundation’s Architectural River Cruise. This cruise takes you along the Chicago River and you’ll discover how this city developed from a small back country outpost into one of the most important crossroads in the world, all in less than 100 years. You’ll get great views of the city from the top of the Sears Tower or enjoy a drink at the Signature Lounge on the 96th floor of the Hancock Building. You can start your Route 66 Journey at a symbolic point if you wish – the Art Institute of Chicago in Grant Park.


From Chicago hit the I-55 to St. Louis. On this 300 mile journey you won’t encounter much until you reach Springfield, the state capital of Illinois. Springfield has preserved sections of Route 66 and most cities along this route play on their Route 66 connections, but isn’t that what it’s all about!

Springfield is a small rural town with character, but still has a lot to offer, notably all of the sites dedicated to Abraham Lincoln. Known as the “Land of Lincoln”, he was buried here after his assassination at the end of the Civil War. It’s well worth it to spend a couple of hours exploring Oak Ridge Cemetery, where you’ll find the Lincoln Tomb, and rumor has it that if you touch the nose of the bronze bust of Lincoln you will have good luck.

St Louis

When you reach St Louis, check into a hotel for the night and spend the remainder of your evening. One of the main attractions in the Gateway City is to take a 630-foot ride to the top of the Gateway Arch for one of the finest views of the city. If it’s a fine day you can see up to 30 miles. If you decide to stay for more than one night then a trip to Six Flags is a must-do.


Next up is Tulsa, Oklahoma. It’s a big, bustling city at the heart of the state of Oklahoma. There is over 140 parks and plenty of cultural attractions to ensure a good time for all ages and interests. You’ll find plenty of trendy nightclubs and restaurants around 34th Street and Pretoria Avenue. Be sure to stop at the retro Metro Diner which is located on old Route 66 and serves pretty good diner food!


Your next port of call should be Amarillo, which is midway across the Texas Panhandle. It’s a busy city that has managed to retain it’s cowboy roots. It is the center of the ranching industry. This city has so much to offer any lover of the Wild West, from gun and saddle shops, to wild-west themed clothing shops.

Amarillo is famous for its steakhouses, which include the Iron Horse Café and the most famous Big Texan Steak Ranch. Here you can get a free 72-ounce steak – the catch? You have to eat it all with a table full of salad, a baked potato and dessert. All in under an hour. Well worth the stopover!


Route 66 will guide you through Albuquerque, New Mexico, past the volcanoes in the far west of the city to the Old Town and the first thing you’re sure to notice is the neon signs that still glow roadside on Central Avenue. These signs are vintage, but you’ll see that businesses old and new have continued to show off their Route 66 roots by embellishing their stores with bright neon lights.

Santa Fe

Enjoy a short drive that brings you to Santa Fe, known as the art centre of the Southwest. Santa Fe is famous for its galleries and museums such as the Museum of Spanish Colonial Art, the Wheelwright Museum of the American Indian and the Museum of Indian Arts and Culture.


Another place worth seeing is Holbrook. This is another old railroad town named after the engineer of the Atlantic and Pacific Railroad. It’s worth noting that on the way to Holbrook you’ll drive through the Petrified Forest National Park. This is the only national park that Route 66 runs through.

Grand Canyon National Park

From Holbrook it’s time to move onto the Grand Canyon National Park. At 277 miles long and 6,000 feet deep the Grand Canyon is one of the new seven wonders of the world which spans over 1.2 million acres. Seeing the Grand Canyon is definitely something that should be on your bucket list. Even if you only give yourself half a day here, hike down into the canyon and get a real sense of its enormous scale. It’s vast existence and peaceful atmosphere is a once in a lifetime experience.

Las Vegas

Enjoy a couple of nights in Las Vegas – the city that offers round the clock entertainment. Stroll down the famous strip and enjoy the amazing themed hotels. Then it’s time for the final stretch of this Route 66 Fly Drive holiday. Make your way to Los Angeles, California through the Mojave Desert, stopping at the ghost town of Calico before terminating in Santa Monica – the end of Route 66.


LA is a city with incredible energy. Surrounded by vast mountain ranges, valleys and forests, the glamour of Hollywood, Beverly Hills, the Sunset Strip and the famous beaches have added to Los Angeles’s reputation as a Californian paradise.

Spend your last few hours relaxing in the California sunshine before returning your rental car at LAX, and begin your journey home.

Route 66 Suggested Itinerary

  • Day 1 : Arrive in Chicago
  • Day 2 : Chicago
  • Day 3 : Chicago – St Louis
  • Day 4 : St Louis – Springfield
  • Day 5 : Springfield – Tulsa – Oklahoma City
  • Day 6 : Oklahoma City - Amarillo
  • Day 7 : Amarillo - Albuquerque
  • Day 8 : Albuquerque
  • Day 9 : Albuquerque – Santa Fe
  • Day 10 : Albuquerque - Holbrook
  • Day 11 : Holbrook – Grand Canyon National Park
  • Day 12 : Grand Canyon National Park/Williams – Las Vegas
  • Day 13 : Las Vegas
  • Day 14 : Las Vegas – Santa Monica/Los Angeles
  • Day 15 : Los Angeles/Santa Monica
  • Day 16 : Los Angeles Departure


To book your ultimate American dream roadtrip along Route 66, call Tour America today on 01-8173535. We specialise in American fly drive holidays and we would love to help you plan your ultimate road trip holiday!

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