Historic Route 66 Holidays from £797

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Your Historic Route 66 Holiday

When adventure calls, answer it with a customised holiday package to Historic Route 66. Wherever it is you're going and whatever your plans are, get set to discover a destination with so much to offer. Why not organise your trip to Historic Route 66 around a few of its most popular cities? Virden, East Gillespie and Gillespie all make great places to start. Whether you're planning to travel on a shoestring or in the lap of luxury, Expedia are here to help you organise your next dream Historic Route 66 holiday.

Top Historic Route 66 Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,019, price is now £797 per person
£797
per person
20 Jan - 24 Jan
found 17 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Amazing view, but basic room

Reviewed on 7 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,082, price is now £813 per person
£813
per person
20 Jan - 24 Jan
found 17 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
Beautiful rooms and service.

Reviewed on 5 Nov 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,018, price is now £1,528 per person
£1,528
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint

Reviewed on 6 Nov 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was £2,673, price is now £2,122 per person
£2,122
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £1,347, price is now £1,074 per person
£1,074
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Historic Route 66 Essential Information

Language
English
Currency
U.S dollars
Top Sights
Arcadia Lake and Flagstaff Convention and Visitors Bureau

Top hotels in Historic Route 66

Ramada by Wyndham Williams/Grand Canyon Area

Ramada by Wyndham Williams/Grand Canyon Area

3 out of 5
950 N Grand Canyon Blvd Williams AZ
Fully refundableReserve now, pay when you stay
The price is £53 per night from 9 Nov to 10 Nov
£53
9 Nov - 10 Nov
includes taxes & fees
Ramada by Wyndham Williams/Grand Canyon Area
The L Motel - Downtown Flagstaff

The L Motel - Downtown Flagstaff

2 out of 5
121 S. Milton Rd Flagstaff AZ
Fully refundableReserve now, pay when you stay
The price is £32 per night from 19 Nov to 20 Nov
£32
19 Nov - 20 Nov
includes taxes & fees
7.4/10 Good! (383 reviews)
"Horrible smell of Fabuloso. The light on the side table wouldn't stay on. The light over the shower had a electrical short and was strobing. Really run down property. The bed made noise every time I moved. The buttons on the AC/heat unit were so worn off was hard to find the power button and the ..."

Reviewed on 5 Nov 2026

The L Motel - Downtown Flagstaff
Quality Inn Holbrook near Petrified Forest

Quality Inn Holbrook near Petrified Forest

2.5 out of 5
2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
The price is £70 per night from 6 Dec to 7 Dec
£70
6 Dec - 7 Dec
includes taxes & fees
Quality Inn Holbrook near Petrified Forest
See all 20,259 properties in Historic Route 66
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Historic Route 66 travel package cost?
Be ready to book, because a getaway to Historic Route 66 starts from just £797. When you combine your hotels, flights and car rentals into a package, you'll enjoy the lowest prices.
If I'm not able to travel, can I cancel my Historic Route 66 travel package?
Don't worry if you're rethinking your Historic Route 66 travel package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We know life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.
How do I get a cheap travel package to Historic Route 66?
Book everything in one place with our Historic Route 66 travel packages. We have incredible bargains on hotels, flights and more that'll keep your wallet happy and adventurous side satisfied. And, with more than 550 air carriers and 1,000,000 properties all over the world to select from, you'll have the flexibility to mix and match as you please.
Does Expedia offer Book Now, Pay Later Historic Route 66 holidays?
We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply pick the payment plan that suits you best during checkout and take away the stress of budgeting for your trip. Don't forget to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you want to grab an awesome deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you secure your getaway.

How far in advance should I book my Historic Route 66 holiday?
While prices do change, we generally advise reserving your seat as soon as possible. Many international airfares become available on Expedia up to 12 months in advance. If you're booking late, you may still get lucky. Cheaper tickets to Historic Route 66 sometimes emerge only weeks before departure.
What does an Expedia Historic Route 66 travel package include?
With Expedia, you can select a combination of hotels, flights and car rentals to build your perfect Historic Route 66 package. Once you've made your booking, you can add on fun stuff like tours and experiences. Remember — the more you bundle, the more deals you'll score!
What should I know before booking a Historic Route 66 travel package?
Locking in all the parts of your holiday together is a simple way to save. Combine your car rentals, flights and hotels into a neat little package. But it's not just hotels. Expedia features all sorts of properties, including holiday rentals such as beach villas and city residences. The list goes on!
Can I choose my airline with a Historic Route 66 Expedia travel package?
You can, and with over 550 airlines to choose from around the world, you're spoiled for choice. Have a look through the available options and find out which airline best fits your needs and budget.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.