Route 66: Eastern Half

12 day self-drive holiday exploring the Eastern half of Route 66

 Includes flights from UK, car hire and accommodation
Fly into Chicago and out of Dallas Fort Worth
You’ll drive approximately 1050 miles in total
 Includes St Louis, Springfield, Kansas State and Oklahoma City
Extra days can easily be added or we can shorten the trip if preferred
Your full road trip pack and itinerary will be sent to you
 Your entire package is ATOL protected

If you want to experience Route 66, but don’t want to drive the entire distance from Chicago or would like to do the trip over two separate holidays, we have a shorter trip which might suit you. You’ll fly to Chicago and, after a couple of days enjoying the Windy City, you’ll begin Route 66 through Illinois, Missouri, Kansas and finally Oklahoma before heading south for your flight home from Dallas, Texas

All our road trips can be shortened or extra nights added or modified with upgraded hotels, car etc. We love building tailor made trips!


Your Itinerary

route 66 chicago
Days 1 - 3:
Begin in Chicago

Arrive in the Windy City, pick up your hire car and spend 2 full days and 3 nights in Chicago. Our recommendations include the Willis Tower, the second tallest building in the USA and the “magnificent mile”.

Fly into Chicago
 Chicago, IL
 4 star hotel
 3 Nights
route 66 illinois
Day 4:
Drive through Illinois

Today you’ll begin your “Mother Road” adventure. Retrace old 66 through Illinois to the State Capital,  Springfield. This city is famously associated with Abraham Lincoln who lived here and is buried in Oak Ridge Cemetery

Approx 200 miles
Springfield, IL
 3 star hotel
route 66 st louis
Day 5:
Towards St Louis

There's just got 100 miles to drive today. You’ll be able to drive a short section of the original brick road in Auburn, Illinois. Just before you arrive in St Louis, take a walk across the “Chain of Rocks” bridge, opened in 1929 to take traffic over the Mississippi River.

Approx 100 miles
St Louis, MO
 3 star hotel
route 66 springfield
Day 6:
Birthplace of Route 66

You’re heading through the Ozark Mountains today towards Springfield in Missouri where, in 1926 a road linking Chicago and Los Angeles was agreed. Originally planned as Route 60, but was finally designated as Route 66.

 Approx 215 miles
Springfield, MO
 Historic hotel
route 66 blue whale catoosa
Day 7:
Three States today

Today, you’ll visit three States! Just after Joplin you’ll leave Missouri and head into Kansas. Don’t blink though - there’s just 13 miles of Route 66 in Kansas! Next up is Oklahoma, and don’t miss the famous Blue Whale of Catoosa!

 Approx 180 miles
Tulsa, OK
 3 star hotel
route 66 oklahoma
Day 8:

Just a short drive today at a mere 115 miles. You’re continuing your journey through Oklahoma - don’t miss the famous “Sidewalk Highway” section of Route 66 between Miami and Afton. So called because it was a single lane, just 9 foot wide section of the original Route 66.

Approx 115 miles
Oklahoma City, OK
 3 star hotel
route 66 cadillac ranch
Days 9 - 10:
Dallas & Fort Worth

You’ve completed your Route 66 trip, today you’ll head down to Texas to spend your final couple of nights in Arlington, between Dallas and Fort Worth. From here you can enjoy the stockyards and ranches of Fort Worth and the city of Dallas.

 Approx 215 miles
Arlington, TX
 3 star hotel
 2 Nights
route 66 blue swallow motel
Day 11:
Final morning

Enjoy the full morning in Texas, maybe visit the 6th Floor museum of the Texas School Book Depository and other JFK related sites in this area. Later today you’ll get your flight home from nearby Dallas Fort Worth Airport. 

Fly out of Dallas FW
route 66 los angeles roadtrip
Day 12: 
Arrive back in UK

You’ll arrive back in the UK today. Thank you for booking your road trip with RouteTrip USA.

Arrive back in UK
 Why not add extra days or some side trips to your holiday? Here’s a few ideas...
Fancy an upgrade?
car upgrade

Our standard prices include a small family car, but you can hire a convertible or SUV. Take a look at your car choice here.

We are completely independent and have a wide choice of hotels. We can upgrade some or all of your hotels. Just ask us!

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All per person prices (pp) shown on this website are based on two adults sharing. Where hotel ratings are shown, these are US ratings, half stars are rounded up to the next full star. RouteTrip USA and RouteTrip are registered trademarks of RouteTrip USA Ltd. *T&Cs Apply. **Subject to availability. ***Refundable deposit required