Historic Route 66 Holidays from AU$2,911

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    Save up to AU$703 when you book a flight and hotel together*
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The Latest Historic Route 66 Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,586 reviews)
Food at the restaurant was good. Rotisserie chicken

Reviewed on 12 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on 11 Aug. 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Location can’t be beat. Hotel is excellent!

Reviewed on 12 Aug. 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Everything was beautiful close to dining and shopping the beds were comfortable it was so relaxing looking out the window unto the ocean. Don’t hesitate book now

Reviewed on 11 Aug. 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
It was exceptional all the way around

Reviewed on 10 Aug. 2025

Historic Route 66 Holiday

Historic Route 66 Essential Information

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

Our pick of the best 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 refundable
The price is AU$252 per night from 24 Aug to 25 Aug
AU$252
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (3,350 reviews)
"Lovely compact hotel"

Reviewed on 11 Aug. 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 AU$242 per night from 1 Sept to 2 Sept
AU$242
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,945 reviews)
"I love the location."

Reviewed on 11 Aug. 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 AU$98 per night from 19 Aug to 20 Aug
AU$98
19 Aug - 20 Aug
includes taxes & fees
8/10 Very Good! (6,754 reviews)
"."

Reviewed on 9 Aug. 2025

The Aquarius Casino Resort, BW Premier Collection
See all 19,126 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 holiday package cost?
Our Historic Route 66 packages, which start at just AU$2,911, 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 holiday 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 holiday?
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 holiday 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 holiday 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 holiday package?
You sure can, and we're here to help. You may be able to cancel or change your Historic Route 66 holiday 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 holiday, take a look at our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.