Historic Route 66 Vacations

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Where to stay in Historic Route 66

Find the best Historic Route 66 areas and neighborhoods for the activities you enjoy most. Learn more about Historic Route 66
Downtown Chicago showing a city

Downtown Chicago

1 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Historic Route 66 Hotel Deals

Central Loop Hotel
Central Loop Hotel
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩193,024 per night from May 28 to May 29
₩193,024
per night
May 28 - May 29
8.4/10 Very Good! (1,619 reviews)
"Lovely room in a fantastic neighborhood right in the thick of it. Surprisingly and delightfully affordable. Folks payin' 3-4X as much as the W just a block away."

Reviewed on May 13, 2024

Central Loop Hotel
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 ₩203,183 per night from May 27 to May 28
₩203,183
per night
May 27 - May 28
8.4/10 Very Good! (3,050 reviews)
"The hotel and staff are great. The beds are terrible, rooms need some maintenance"

Reviewed on May 15, 2024

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 ₩199,915 per night from May 27 to May 28
₩199,915
per night
May 27 - May 28
7.6/10 Good! (6,748 reviews)
"All has gone as planned. Check in was quick and the ice machine on the 7th floor works. What a bonus."

Reviewed on May 17, 2024

Congress Plaza Hotel
See all 18,698 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 , 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.

Discover the most popular places to visit in Historic Route 66

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.