Historic Route 66 Holidays from AU$3,133

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The Latest Historic Route 66 Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was AU$4,184, price is now AU$3,133 per person
AU$3,133
per person
5 Sept - 12 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (2,618 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$5,385, price is now AU$3,627 per person
AU$3,627
per person
5 Sept - 12 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Friendly competent staff at checkin. The room and the view were spectacular. Wish we would have had time to use more of the amenities. I’d stay again if the opportunity arises.

Reviewed on 16 July 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$6,677, price is now AU$4,776 per person
AU$4,776
per person
5 Sept - 12 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$4,911, price is now AU$3,646 per person
AU$3,646
per person
5 Sept - 12 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
I love all about this hotel

Reviewed on 15 July 2026

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Price was AU$4,565, price is now AU$3,396 per person
AU$3,396
per person
5 Sept - 12 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (3,475 reviews)

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

Ramada by Wyndham Williams/Grand Canyon Area

Ramada by Wyndham Williams/Grand Canyon Area

3 out of 5
950 N Grand Canyon Blvd Williams AZ
Fully refundableReserve now, pay when you stay
The price is AU$120 per night from 27 July to 28 July
AU$120
27 July - 28 July
includes taxes & fees
Ramada by Wyndham Williams/Grand Canyon Area
The L Motel - Downtown Flagstaff

The L Motel - Downtown Flagstaff

2 out of 5
121 S. Milton Rd Flagstaff AZ
Fully refundableReserve now, pay when you stay
The price is AU$70 per night from 19 July to 20 July
AU$70
19 July - 20 July
includes taxes & fees
7.4/10 Good! (282 reviews)
"Couldn’t find the remote for the air conditioning"

Reviewed on 6 July 2026

The L Motel - Downtown Flagstaff
Quality Inn Holbrook near Petrified Forest

Quality Inn Holbrook near Petrified Forest

2.5 out of 5
2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 2 Aug to 3 Aug
AU$138
2 Aug - 3 Aug
includes taxes & fees
8.8/10 Excellent! (748 reviews)
"TV remote did not work well."

Reviewed on 16 July 2026

Quality Inn Holbrook near Petrified Forest
See all 19,787 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$3,133, 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.

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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.