Historic Route 66 Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top Historic Route 66 Vacation 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
Save 100% on your flight
per person
Oct 11 - Oct 15
found 14 hours ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Will go back again for next Chicago trip

Reviewed on Jul. 21, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Just a great property- really a 5 star experience-great location

Reviewed on Jul. 20, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 11 - Oct 15
found 16 hours ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
Nice rooms and amenities, we would stay here again. This was a nice place! We love the location and the fact it was dog friendly. Lots to do for eats/drinks in walking distance and they have a lovely dog area adjacent to the pool on the 8th floor. Nice not to have to go down to the street for potty breaks. Taking off a star for the simple fact that they only have feather pillows (so I had to buy my own hypoallergenic one) and their parking lot was full so we had to park a few blocks away.

Reviewed on Jul. 19, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
The property in itself was not terrible, but I expected better.

Reviewed on Jul. 19, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
Beautiful location, very professional staff

Reviewed on Jul. 21, 2025

Ready to book your vacation to Historic Route 66?

 

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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 $159 per night from Aug 10 to Aug 11
CA $159
CA $187 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (3,341 reviews)
"Good for an overnight while in transit but not for a stay. Few amenities. No fridge. Very clean."

Reviewed on Jul. 18, 2025

Club Quarters Hotel, Central Loop, Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is CA $184 per night from Aug 18 to Aug 19
CA $184
CA $216 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (8,878 reviews)
"Great place to stay."

Reviewed on Jul. 19, 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 Jul 22 to Jul 23
CA $54
CA $96 total
Jul 22 - Jul 23
includes taxes & fees
8/10 Very Good! (6,609 reviews)
"Dont feel like it"

Reviewed on Jul. 19, 2025

The Aquarius Casino Resort, BW Premier Collection
See all 19,142 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Historic Route 66 vacation package cost?
Our Historic Route 66 packages, which start at just CA $1,492, 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.