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 Route 66: Eastern Half

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

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!

 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
Your trip can be tailored to suit your needs. 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
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Your Itinerary

route 66 chicago

Days 1 - 3:
Chicago (3 nights)

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

Collect
Car

Chicago,
IL

4 Star
Hotel

il%20springfield%20lincolns%20home

Day 4:
Springfield, Illinois

Today you’ll begin your “Mother Road” adventure. Retrace old 66 through Chicago, through rural Illinois into Springfield where Abraham Lincoln lived prior to his presidency. You can visit his home and burial places.  

200
miles

Springfield,
IL

3 Star
Hotel

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Day 5:
St Louis

There's just 100 miles to drive to St Louis, known as the Gateway to the West. You’ll be able to drive a short section of the original brick road in Auburn, Illinois before walking the “Chain of Rocks” bridge, opened in 1929 to take traffic over the Mississippi River.

100
miles

St Louis,
MO

3 Star
Hotel

route 66 springfield

Day 6:
Springfield, Missouri

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. Springfield is known as the birthplace of Route 66.

215
miles

Springfield,
MO

Historic
Hotel

route 66 oklahoma

Day 7:
Tulsa

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 - but they’re a good 13 miles! Next up is Oklahoma, and don’t miss the famous Blue Whale of Catoosa!

180
miles

Tulsa,
OK

3 Star
Hotel

route 66 texas

Day 8:
Oklahoma

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.

115
miles

Oklahoma City, OK

3 Star
Hotel

route 66 cadillac ranch

Days 9 & 10:
Arlington (2 nights)

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.

215
miles

Arlington,
TX

3 Star
Hotel

route 66 blue swallow motel

Days 11 & 12:
Texas & Fly Home

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. This evening you’ll catch your overnight flight back to the UK.

Return
Car

Fly
Home

Fancy an upgrade?
car upgrade

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

Hotels
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. ***On request, subject to availability and refundable deposit required