Historic Route 66 Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 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

Top Historic Route 66 Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 31 - Aug. 3
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (664 reviews)
Nice property, excellent service. Hallways are showing a little wear. We have visited the Emily since its opening. Great neighborhood and nice hotel. Just a bit worn in the 3rd floor hallway.

Reviewed on Jun. 2, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 12 - Aug. 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Very nice staff except for the guy at the front desk with the hair braided back very rude. I pray I never encounter him again I come to the Trump all the time and this was my first encounter with him very unwelcoming and dry.

Reviewed on Jun. 4, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 12 - Aug. 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (703 reviews)
The Art Deco architectural beauty of this hotel is stunning! Every time I was in the elevator area, I was wowed. We had a corner room on the 22nd floor and it was great. Lots of space and great art deco inspired furniture and lights. We had a view of the bridge and the lake. The breakfast at the French cafe was so so. Overall I highly recommend this hotel.

Reviewed on May 30, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 13 - Aug. 17
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 12 - Aug. 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (3,522 reviews)
Best hotel in all of Chicago. This place is unreal. You cannot find better views in the city.

Reviewed on Jun. 5, 2024

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

2 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

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 CA $221 per night from Jun. 16 to Jun. 17
CA $221
CA $259 total
includes taxes & fees
Jun 16 - Jun 17
8.4/10 Very Good! (3,080 reviews)
"Front desk help was amazing"

Reviewed on Jun. 2, 2024

Club Quarters Hotel, Central Loop, Chicago
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 CA $221 per night from Jun. 16 to Jun. 17
CA $221
CA $259 total
includes taxes & fees
Jun 16 - Jun 17
8.4/10 Very Good! (1,627 reviews)
"Very central location, clean, friendly staff, and affordable."

Reviewed on Jun. 5, 2024

Central Loop Hotel
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 CA $204 per night from Jun. 16 to Jun. 17
CA $204
CA $239 total
includes taxes & fees
Jun 16 - Jun 17
7.6/10 Good! (6,849 reviews)
"Great location, historic feel. Pleasant stay"

Reviewed on Jun. 4, 2024

Congress Plaza Hotel
See all 18,712 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Historic Route 66 vacation package cost?
Our Historic Route 66 packages, which start at just CA $992, 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(158 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(141 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(459 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.