Historic Route 66 Holidays from AU$1,932

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

The Latest Historic Route 66 Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Morton Grove/Chicago

Super 8 by Wyndham Morton Grove/Chicago

2 out of 5
per person
12 Aug - 16 Aug
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
6.6/10 (1,004 reviews)
They were nice and approachable

Reviewed on 29 Jun. 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
12 Aug - 16 Aug
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Great stay. Elevators were a lot slow but overall great property and great service!

Reviewed on 6 Jul. 2025

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
12 Aug - 16 Aug
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (1,564 reviews)
It's not insanely close to restaurants but it's a good location nonetheless.

Reviewed on 6 Jul. 2025

La Quinta by Wyndham Chicago O'Hare Airport

La Quinta by Wyndham Chicago O'Hare Airport

3 out of 5
O'Hare
per person
12 Aug - 16 Aug
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,580 reviews)
I had a cancelled flight and this was a perfect location. 10 minutes from the airport free shuttle breakfast in the morning. A spacious room.

Reviewed on 7 Jul. 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
per person
12 Aug - 16 Aug
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
7.6/10 Good! (1,001 reviews)
I liked that it was clean, new and spacious, though the bathroom could've been a little bigger. Didn't like that only one elevator was available with unaccessible staircase. Does this meet fire safety standards ? A light continental breakfast would've been nice.

Reviewed on 5 Jul. 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
The price is AU$303 per night from 9 July to 10 July
AU$303
9 July - 10 July
includes taxes & fees
8.6/10 Excellent! (3,350 reviews)
"Staff was very friendly. Very helpful."

Reviewed on 5 Jul. 2025

Club Quarters Hotel, Central Loop, Chicago
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$106 per night from 9 July to 10 July
AU$106
9 July - 10 July
includes taxes & fees
8/10 Very Good! (6,519 reviews)
"."

Reviewed on 6 Jul. 2025

The Aquarius Casino Resort, BW Premier Collection
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is AU$526 per night from 7 Aug to 8 Aug
AU$526
7 Aug - 8 Aug
includes taxes & fees
9/10 Wonderful! (1,978 reviews)
"Great hotel."

Reviewed on 5 Jul. 2025

InterContinental Chicago Magnificent Mile by IHG
See all 18,936 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Historic Route 66 holiday package cost?
Our Historic Route 66 packages, which start at just AU$1,932, 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.