A mural on a building with a man holding a machine and a sign that says "THIS LAND IS YOUR LAND".

Historic Route 66 Vacations from $289

Book a Hotel + Flight or Car together to unlock savings

The Latest Historic Route 66 Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 11 - Dec 14

    The Wildwood Hotel + Flight

    Wildwood
    3 nights
    3.5 star property
    9.2/10 - Wonderful (1,682 reviews)
    "Everything was good. Seemed that the property was not full but we were forced into a suite."
    Reviewed November 7, 2026
    Roundtrip • Atlanta (ATL) - St. Louis (STL)
    ATL - STL • Nonstop STL - ATL • Nonstop
    $539
    $289
    per traveler
    found 2 days ago
    The Wildwood Hotel
  • Jan 15 - Jan 18

    Rosewood Inn of the Anasazi + Flight

    Downtown Santa Fe
    3 nights
    5.0 star property
    9.6/10 - Exceptional (925 reviews)
    Roundtrip • Dallas (DFW) - Albuquerque (ABQ)
    DFW - ABQ • Nonstop ABQ - DAL • Nonstop
    $1,796
    $1,167
    per traveler
    found 1 day ago
    Rosewood Inn of the Anasazi
  • Dec 10 - Dec 14

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (5,662 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $837
    $549
    per traveler
    found 2 days ago
    Hotel Riu Plaza Chicago
  • Dec 10 - Dec 14

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (195 reviews)
    "Hotel was very nice and clean. The location was excellent."
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $813
    $547
    per traveler
    found 2 days ago
    The Talbott, Autograph Collection
  • Dec 10 - Dec 14

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,896 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $939
    $657
    per traveler
    found 2 days ago
    LondonHouse Chicago, Curio Collection by Hilton

Historic Route 66 Hotel Deals

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

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.

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