Historic Route 66 Vacations from ₩799,860
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The Latest Historic Route 66 Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
₩999,804
per person
Sep 12 - Sep 13
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
The hotel itself is nice! But I want to write a review about the STAFF! I have never stayed in a hotel where the staff is so well trained, professional, respectful, serving with positive attitude and smile, make you feel at home, spoil you and so much more! I absolutely wanted to stay longer because of the TOP NOTCH SERVICE! We need to give credits where credit is due and THIS is one of them!
Another positive point was our room had a kitchenette with stove, utensils, a FULL BAR WITH AFFORDABLE PRICES!!! The room service is open 24/7 and that’s something rare that a lot of hotels don’t have!
The bathtub was huge 🥰😍 Probablt my favorite amenities! Loved how the rooms were cleaned by the staff! We didn’t even have to ask! I have so many positive things to say! ABSOLUTELY RECOMMEND THIS HOTEL! You won’t regret it! ❤️❤️❤️
Reviewed on Aug 10, 2026
Swissotel - Chicago
Downtown Chicago
₩927,070
per person
Sep 12 - Sep 13
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
The rooms are definitely not as nice as the pictures on the site makes them seem. My card got charged multiple times for unknown reasons. I brought it up to the front desk and they were very nice and the charges ended up going away, but still frustrating. Parking is ridiculously expensive for what it is. I do feel like they’re trying to scam you out on money every chance they get (i.e. charging $30 a night for a “service fee”). I don’t think it was worth the money considering there’s no pool or continental breakfast. I’m not sure I would stay here again.
Reviewed on Aug 9, 2026
Renaissance Chicago Downtown Hotel
Downtown Chicago
₩831,686
per person
Sep 12 - Sep 13
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
We enjoyed our stay at Renaissance. The staff were amazing! I especially want to highlight Jon from concierge. He was wonderful to work with and helped make our sister’s birthday special. The only negative is that the hotel is dated as far as the rooms and they could’ve been cleaner. We also didn’t get a chance to utilize the resort fee amenities so we feel like money was wasted there. I wish that was optional.
Reviewed on Aug 9, 2026
Find the Best Historic Route 66 Vacation Packages
Historic Route 66 Hotel Deals
Ramada by Wyndham Williams/Grand Canyon Area
950 N Grand Canyon Blvd Williams AZ
Fully refundableReserve now, pay when you stay
₩88,554
₩104,406 total
Aug 16 - Aug 17
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"Staff was nice, but they were hanging out at the restaurant for some time while we and others were waiting in the lobby."
Reviewed on Aug 9, 2026
Quality Inn Holbrook near Petrified Forest
2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
₩125,440
₩145,988 total
Sep 6 - Sep 7
includes taxes & fees
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood
14125 Hwy Z, I-44 and Hwy 28 Exit 163 St. Robert MO
Fully refundableReserve now, pay when you stay
₩89,751
₩98,254 total
Sep 5 - Sep 6
includes taxes & fees
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 ₩799,860, 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.
