Historic Route 66 Holidays from £982

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
8 Sept - 12 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Great helpful staff! Very clean! Wonderful experience! Breakfast buffet is a must! So delicious

Reviewed on 31 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.

Reviewed on 30 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Sept - 30 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (229 reviews)
Room was clean, balcony had a nice view, bed were comfortable, shower was nice

Reviewed on 31 Jul 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

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

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Fully refundable
The price is £96 per night from 24 Aug to 25 Aug
£96
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (3,382 reviews)
"Good location"

Reviewed on 30 Jul 2025

Club Quarters Hotel, Central Loop, Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £119 per night from 1 Sept to 2 Sept
£119
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (9,038 reviews)
"This was a nice option for my wife and I . Nice location plenty of dining with in walking distance. Highly recommend this hotel"

Reviewed on 29 Jul 2025

Congress Plaza Hotel
Avi Resort & Casino

Avi Resort & Casino

3.5 out of 5
10000 Aha Macav Pkwy, Laughlin, NV
The price is £24 per night from 25 Aug to 26 Aug
£24
25 Aug - 26 Aug
includes taxes & fees
8/10 Very Good! (3,992 reviews)
"Is a family place great pool and river area..rooms need more attention, food okay,,but everyone was so nice from every department.."

Reviewed on 30 Jul 2025

Avi Resort & Casino
See all 19,188 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 £982. 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.

* 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.