Historic Route 66 Vacation Packages

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Top Historic Route 66 Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,617 reviews)
Excellent stay. Awesome views of the city. Very close by to everything in downtown.

Reviewed on Aug. 14, 2025

The Inn at Vanessie

The Inn at Vanessie

4.5 out of 5
Downtown Santa Fe
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albuquerque (ABQ)
8.8/10 Excellent! (1,000 reviews)
Such a charming hotel. Love the lobby and room decor. Such a beautiful lobby and cozy bar. So close to everything..crepes, museums, the square, oven fired pizza...great shopping for the ladies and good shops for men. We visited in August..would love to see it at Christmas. Sante fe is so great in so many ways...wish i lived closer

Reviewed on Aug. 10, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Food prices parking prices

Reviewed on Aug. 13, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Food is good, like most other hotels. We like waffle particularly.

Reviewed on Aug. 13, 2025

The Hacienda & Spa at Hotel Santa Fe

The Hacienda & Spa at Hotel Santa Fe

4.5 out of 5
Downtown Santa Fe
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albuquerque (ABQ)
9.4/10 Exceptional! (959 reviews)
Slept great, bed was very comfortable and the Amaya restaurant on site is very good! Great service!!

Reviewed on Aug. 11, 2025

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Historic Route 66 Hotel Deals

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Sep 14 to Sep 15
CA $94
CA $111 total
Sep 14 - Sep 15
includes taxes & fees
8.6/10 Excellent! (3,355 reviews)
Amazing Experience, Highly Recommend
"Amazing experience. The room was small but we didn't stay in there long enough to care. The best parts of this hotel are the staff and the restaurant under it. I can't say enough great things about that restaurant: "Elephant and Something". The food was amazing, best we had in the city and the drinks ..."

Reviewed on Aug. 11, 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 CA $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,958 reviews)
"Super convenient to everything we needed or wanted Hotel is good, location is great"

Reviewed on Aug. 11, 2025

Congress Plaza Hotel
The Aquarius Casino Resort, BW Premier Collection

The Aquarius Casino Resort, BW Premier Collection

3.5 out of 5
1900 S Casino Dr, Laughlin, NV
Fully refundableReserve now, pay when you stay
The price is CA $47 per night from Aug 18 to Aug 19
CA $47
CA $88 total
Aug 18 - Aug 19
includes taxes & fees
8/10 Very Good! (6,798 reviews)
"Hotel was clean, bed was comfortable. Had a view of the river. Pool was refreshing. Hot Tub could have been warmer."

Reviewed on Aug. 13, 2025

The Aquarius Casino Resort, BW Premier Collection
See all 19,125 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.
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Frequently asked questions

How much does a Historic Route 66 vacation package cost?
Our Historic Route 66 packages, which start at just CA $655, 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.