Historic Route 66 Vacations from $234

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The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $425, price is now $234 per person
$234
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,389, price is now $377 per person
$377
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,664, price is now $945 per person
$945
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $444, price is now $261 per person
$261
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $690, price is now $406 per person
$406
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
The stay was everything I love the view and peaceful. Thank you

Reviewed on Oct 26, 2026

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Historic Route 66 Hotel Deals

Ramada by Wyndham Williams/Grand Canyon Area

Ramada by Wyndham Williams/Grand Canyon Area

3 out of 5
950 N Grand Canyon Blvd Williams AZ
Fully refundableReserve now, pay when you stay
$52 nightly
The price is $61 total per night from Nov 3 to Nov 4
$61 total
Nov 3 - Nov 4
Total with taxes and fees
7.8/10 Good! (1,008 reviews)
"The door had prior damage, was not properly repaired. The walls had damage. The carpet had a very large stain. The bath faucet leaked. The sink had no stopper. Two of the bath towels left a long hair on my face, so their laundry process is not adequate. I wanted an upstairs room for quiet. They gave ..."

Reviewed on Oct 26, 2026

Ramada by Wyndham Williams/Grand Canyon Area
The L Motel - Downtown Flagstaff

The L Motel - Downtown Flagstaff

2 out of 5
121 S. Milton Rd Flagstaff AZ
Fully refundableReserve now, pay when you stay
$44 nightly
The price is $49 total per night from Oct 28 to Oct 29
$49 total
Oct 28 - Oct 29
Total with taxes and fees
7.4/10 Good! (374 reviews)
"Would not recommend"

Reviewed on Oct 25, 2026

The L Motel - Downtown Flagstaff
Quality Inn Holbrook near Petrified Forest

Quality Inn Holbrook near Petrified Forest

2.5 out of 5
2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $96 total per night from Nov 25 to Nov 26
$96 total
Nov 25 - Nov 26
Total with taxes and fees
Quality Inn Holbrook near Petrified Forest
See all 20,505 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.

Find the Best Historic Route 66 Vacation Packages

Historic Route 66 Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

What's included in a Historic Route 66 vacation package?
A Historic Route 66 vacation package lets you combine flights, hotel stays, and rental cars, making it easy to plan your adventure along this iconic route.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Historic Route 66 vacation package?
When you bundle, you can save up to 30%*. To save money on a Historic Route 66 package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What is the best time to visit Historic Route 66?
Historic Route 66 is popular with travelers throughout the year, offering a classic American road trip experience across various seasons. Since specific peak travel times or major events are not consistently highlighted for the entire route, travelers can plan their Historic Route 66 vacation based on personal preferences for weather and crowd levels in the specific states they plan to visit.
Is Historic Route 66 better suited for a beach vacation or a cultural trip?
Historic Route 66 is primarily an outdoor and nature destination, known for adventure activities and scenic views.

Travelers can find family-friendly attractions and entertainment options along the route, such as the Route 66 Raceway for motorsports enthusiasts and the Great Wolf Lodge Water Park for aquatic fun. The destination emphasizes outdoor activities and exploration.

A Historic Route 66 vacation is best suited for those seeking adventure, road trips, and family entertainment, with opportunities to experience classic Americana and diverse landscapes.
Which airport should I use for a Historic Route 66 vacation?
For a Historic Route 66 vacation, a primary gateway is Oklahoma City, OK (OKC-Will Rogers World), which serves a significant portion of the route. Another convenient option is Lawton, OK (LAW-Lawton-Fort Sill Regional).

Travelers can also consider smaller regional airports like Clinton, OK (CSM-Clinton-Sherman Industrial and CLK-Clinton Municipal), and Altus, OK (AXS-Altus Municipal), depending on the specific segment of Historic Route 66 they plan to explore.
Can I change or cancel my Historic Route 66 vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Historic Route 66 vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Historic Route 66 vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Historic Route 66 vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Historic Route 66?
To find last-minute vacation packages to Historic Route 66, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Historic Route 66 vacation packages?
Free cancellation on a Historic Route 66 vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Historic Route 66 vacation as a package or separately?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Historic Route 66 getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Historic Route 66 vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

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