Historic Route 66 Vacations from ￥214,943

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    Save up to ￥45,448 when you book a flight and hotel together*
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The Latest Historic Route 66 Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on Jul 27, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Bad room service, bad dinner/breakfast service at the restaurants and no house keeping - had to ask for it - and when they finally did they didn’t restock the bar or towels.

Reviewed on Aug 4, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
Beautiful hotel close to all the best parts of Chicago. Wonderful stay. Cant wait to go back!

Reviewed on Aug 5, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.

Reviewed on Aug 1, 2025

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 23 - Oct 27
found 18 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
8.4/10 Very Good! (1,552 reviews)
Check in was at 3 and i git a room at 5

Reviewed on Aug 5, 2025

Find the Best Historic Route 66 Vacation Packages

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 ￥24,436 per night from Aug 17 to Aug 18
￥24,436
￥28,685 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (3,348 reviews)
"Nice location"

Reviewed on Aug 1, 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 ￥19,724 per night from Sep 1 to Sep 2
￥19,724
￥23,154 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,956 reviews)
"We stayed in a family suite. Both rooms were large. The beds were comfortable."

Reviewed on Aug 4, 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 ￥5,730 per night from Aug 6 to Aug 7
￥5,730
￥10,248 total
Aug 6 - Aug 7
includes taxes & fees
8/10 Very Good! (6,723 reviews)
Best Hotels in Laughlin
"I never imagined there would be such a nice hotel in the middle of the desert."

Reviewed on Aug 4, 2025

The Aquarius Casino Resort, BW Premier Collection
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.

Frequently asked questions

How much does a Historic Route 66 vacation package cost?
Our Historic Route 66 packages, which start at just ￥214,943, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.