Route 66 - East Vacation Packages
Route 66 is one of the most legendary roadways in U.S. history. First opened in 1926, it stretches for 2,448 miles, with 1,063 of those miles located on the eastern portion of the route, passing through the states of Illinois, Missouri, Kansas and Oklahoma. Go on a delightful journey that is chock full of Americana, from Chicago all the way through the towns of western Oklahoma, stopping along the way in cities such as Springfield, Illinois; St. Louis; Springfield, Missouri; Tulsa; and Oklahoma City.
Best Vacation Packages:
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7 nights from $985*More details›
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Major Cities
Sections of Route 66
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The Central portion of Route 66 takes you through the enchanting Southwest, through the states of Texas, New Mexico, and Arizona.
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The westernmost portion of Route 66 takes you through the Golden State of California to the end of the line in Santa Monica, passing through cities like Los Angeles along the way.
More to Explore
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The West Coast
Experience an unforgettable vacation exploring the fantastic Pacific West Coast Region including Washington, Oregon, and California along with the awe-inspiring charms of Alaska.
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The Rocky Mountains
The Rocky Mountains stretch some 3,000 miles from British Columbia and Alberta in Canada through Idaho, Montana, Wyoming, Colorado, and down to New Mexico in the U.S.
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The Southwest
The sprawling region of The Southwest of the United States encompasses four large states; Arizona, New Mexico, Oklahoma, and Texas. Home to spectacular natural wonders such as the Grand Canyon and Monument Valley spread throughout miles of wide-open spaces and varied terrains.
SUGGESTED ITINERARIES
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Chicago and Illinois State Beach (Self Drive)More details› - Flight into and out of Chicago
- Rental Car for 7 days
- Hotel for 3 nights in Chicago, IL
- Hotel for 3 nights in Illinois Beach State Park, IL
Driving Time
Chicago, IL- Illinois Beach State Park, IL: 1 hr 12 mins. approx.-
Route 66 Origins Self Drive (Chicago - Springfield - St Louis - Tulsa - Oklahoma City - Amarillo)15 nights from $2,039*›
- Flight into Chicago and out of Amarillo
- Rental Car for 13 days
- Hotel for 3 nights in Chicago
- Hotel for 2 nights in Springfield, IL
- Hotel for 2 nights in St. Louis
- Hotel for 2 nights in Springfield, MO
- Hotel for 2 nights in Tulsa
- Hotel for 2 nights in Oklahoma City
- Hotel for 2 nights in Amarillo
Driving Time
Chicago– Springfield, IL: 3 hrs. 14mins. approx.
Springfield, IL- St. Louis: 1 hr. 28 mins. approx.
St. Louis- Springfield, MO: 3 hrs. 22 mins. approx.
Springfield, MO- Tulsa: 3 hrs approx.
Tulsa - Oklahoma City: 1 hr 34 mins. approx.
Oklahoma City - Amarillo: 4 hrs. approx.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!
Interests
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California is the Golden State and is world-renowned for its iconic beaches and city destinations. The stunning state stretches for almost 900 miles along the Pacific Coast to the border of Mexico and boasts beautiful beaches along the way.
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The United States boasts 62 protected National Parks spread throughout 29 states covering approximately 52.2 million acres of land. To be classed as a National Park these natural areas must provide an outstanding region of beauty, an unusual ecosystem, or a plethora of recreational activities.
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Bottomless snow, rugged peaks and beauty galore, the southwest seems to have been designed exactly as a skiing destination. The region also offers plenty of relaxation opportunities after hitting the slopes.
USA Customer Reviews
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Overall, my experience, the trip masters was good, but but I had a problem you couldn’t help. The reason I say this is that we had a problem with a ho ...Traveled on: 9/24/2026
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The hotel in Washington DC was very small and the bathroom offered little space and privacy. However, the hotel was eccentric and had fun decorations. ...Traveled on: 8/24/2026
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You guys are great! Keep being awesome ...Traveled on: 6/12/2026
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It was an excellent trip ...Traveled on: 6/5/2026
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I liked the car rental, hotels, flights, and locations. It was quite an adventure! It would have been nice to know of the one-way car rental fee more ...Traveled on: 3/29/2026