Historic Route 66 Vacations from ￥285,926
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Historic Route 66 Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥441,612
per person
Nov 1 - Nov 7
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Main lobby, rooftop patio and breakfast dining room were great. The room furniture was a little tired looking. The bed was problematic: the mattress was way too soft, the sheets were never tucked into the bed so the slid all over the place and the blanket was not a duvet it was an old fashioned wool type (which I haven’t seen in years). The staff everywhere were lovely and took care of any questions or requests we had promptly.
Reviewed on Aug 15, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
￥413,212
per person
Nov 1 - Nov 7
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
Staff was very nice and friendly including valet. Enjoyed the location. The AC was too loud at night
Reviewed on Aug 15, 2026
Find the Best Historic Route 66 Vacation Packages
Historic Route 66 Hotel Deals
Ramada by Wyndham Williams/Grand Canyon Area
950 N Grand Canyon Blvd Williams AZ
Fully refundableReserve now, pay when you stay
￥9,886
￥11,656 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Just a stop over hotel, but it was well run and managed and we enjoyed it."
Reviewed on Aug 15, 2026
Quality Inn Holbrook near Petrified Forest
2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
￥14,769
￥17,188 total
Sep 6 - Sep 7
includes taxes & fees
8.8/10 Excellent! (790 reviews)
"We needed a place to sleep on our trip back to Texas. We pulled in late. The lot was full. Very safe and clean. An older town and property but felt clean and had a lovely staff. Next morning we were the only car in lot at 8 am. Had breakfast and a coffee in the common area, which was also bright ..."
Reviewed on Aug 15, 2026
The L Motel - Downtown Flagstaff
121 S. Milton Rd Flagstaff AZ
Fully refundableReserve now, pay when you stay
￥9,177
￥10,221 total
Aug 16 - Aug 17
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Historic Route 66 vacation package cost?
Our Historic Route 66 packages, which start at just ￥285,926, are an easy way to save big bucks. Pick your preferred flights, hotels and rental cars to create your ideal trip.
How do I get a cheap travel package to Historic Route 66?
Book everything all in one place with our Historic Route 66 vacation packages. We have incredible bargains on hotels, flights and more that'll keep your hip pocket happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 properties globally to select from, you'll have the flexibility to mix and match as you please.
What are the top hotels in Historic Route 66?
If you're headed to Gillespie, you can't go past Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton. Both are excellent bases for exploring this lively Historic Route 66 city.
How far in advance should I book my Historic Route 66 vacation?
The earlier you book, the better. Airlines usually release flight tickets nearly 12 months prior to departure, and this is a fantastic opportunity to pick up some of the lowest prices. Just been told you need to take your vacation time next month? That's alright! Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Historic Route 66 travel package include?
You can select from a combination of hotels, flights and rental cars. Once you've made your booking, you can add the fun stuff like activities and experiences. Want to pick your fare class? That's possible too. The choice is all yours when it comes to crafting your dream Historic Route 66 getaway.
What should I know before booking a Historic Route 66 travel package?
An Expedia travel package can be tailored to your budget and is a fantastic way to make your hard-earned dollars stretch further. How little or much you include is totally up to you. Hotels, rental cars and flights — come up with a combination that suits your plans.
Can I choose my airline with a Historic Route 66 Expedia vacation package?
Yes, definitely. Expedia has more than 550 airline partners to pick from around the globe. With such a big range of choice, finding the perfect carrier to take you to Historic Route 66 shouldn't be hard.
If I'm not able to travel, can I cancel my Historic Route 66 vacation package?
You sure can, and we're here to help. You may be able to cancel or change your Historic Route 66 vacation package for free if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your vacation, take a look at our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
