Historic Route 66 Holidays from AU$2,912

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The Latest Historic Route 66 Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Spark by Hilton Merrillville

Spark by Hilton Merrillville

3 out of 5
Price was AU$2,957, price is now AU$2,912 per person
AU$2,912
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (52 reviews)
Excellent all around, very nice place to stay.

Reviewed on 24 Aug. 2025

Hilton Garden Inn Merrillville

Hilton Garden Inn Merrillville

3 out of 5
Green Acres
Price was AU$3,547, price is now AU$3,196 per person
AU$3,196
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The staff were absolutely wonderful. Everything was clean and they had an open bar and the bartender was absolutely amazing. The lady at the front desk couldn’t have been more helpful. It had been a long trip and they were right there, waiting on us hand and foot.

Reviewed on 19 Aug. 2025

Hampton Inn by Hilton Merrillville

Hampton Inn by Hilton Merrillville

2.5 out of 5
Price was AU$3,115, price is now AU$2,930 per person
AU$2,930
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.6/10 Excellent! (805 reviews)
Convenient to shops and restaurants.

Reviewed on 2 Aug. 2025

Tru By Hilton Merrillville

Tru By Hilton Merrillville

2.5 out of 5
Price was AU$3,074, price is now AU$3,020 per person
AU$3,020
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (273 reviews)
Property was clean and the staff was outstanding.

Reviewed on 26 Aug. 2025

Homewood Suites by Hilton Munster

Homewood Suites by Hilton Munster

3 out of 5
Price was AU$3,033, price is now AU$2,981 per person
AU$2,981
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
I love how kind the staff was , they were amazing!

Reviewed on 22 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
The price is AU$210 per night from 2 Sept to 3 Sept
AU$210
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (3,358 reviews)
"Great location, quiet rooms"

Reviewed on 25 Aug. 2025

Club Quarters Hotel, Central Loop, Chicago
Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street, Chicago, IL
The price is AU$210 per night from 2 Sept to 3 Sept
AU$210
2 Sept - 3 Sept
includes taxes & fees
Central Loop Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$273 per night from 1 Sept to 2 Sept
AU$273
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,218 reviews)
"Friendly"

Reviewed on 24 Aug. 2025

The Wade
See all 19,174 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$2,912, 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.