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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Jul. 30, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Bathroom would be better with 2 bathrooms and one live outlet to enable charging devices while out of the room.

Reviewed on Jul. 30, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
It was a great location , close to downtown core.

Reviewed on Jul. 30, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
Excellent location and beautiful property.

Reviewed on Jul. 30, 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 $151 per night from Aug 24 to Aug 25
CA $151
CA $177 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (3,378 reviews)
Satisfied customer
"Good customer service, very accommodating, great location as it was close to most major attractions. The value for the price was excellent! I would book here again."

Reviewed on Jul. 29, 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 $186 per night from Aug 18 to Aug 19
CA $186
CA $218 total
Aug 18 - Aug 19
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 Jul. 29, 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 $54 per night from Aug 3 to Aug 4
CA $54
CA $96 total
Aug 3 - Aug 4
includes taxes & fees
8/10 Very Good! (6,732 reviews)
"Only area that needs to improve is the casino we waitresses.Take too long to bring drinks or don't even bring them. I had to ask a few times to different personnel when I asked for drinks."

Reviewed on Jul. 28, 2025

The Aquarius Casino Resort, BW Premier Collection
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.
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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 $957, 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.