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

Historic Route 66 Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

The Latest Historic Route 66 Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.
    Jan 7 - Jan 11

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,566 reviews)
    "Breakfast was good"
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,051
    CA $758
    per traveller
    found 21 hours ago
    Swissotel - Chicago
  • A cityscape with modern high-rise buildings, a river, and a bridge.
    Dec 19 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,874 reviews)
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YHM • 1 stop
    CA $2,730
    CA $1,208
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.
    Dec 27 - Jan 2

    Park Hyatt Chicago + Flight

    Downtown Chicago
    6 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."
    Reviewed November 4, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    Save 100% on your flight
    CA $3,612
    CA $2,536
    per traveller
    found 4 hours ago
    Park Hyatt Chicago
  • A modern lobby with a sofa, coffee table, and potted plants.
    Jan 7 - Jan 11

    The Emily Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,357 reviews)
    "Our stay at The Emily Hotel was outstanding! The entire property was well-maintained and the customer service provided by Leo and his team was excellent! We thoroughly enjoyed the offerings at Flora and were able to experience a Rooftop Cinema event! The hotel is conveniently located in walking distance to great restaurants and the L. I highly recommend The Emily Hotel and look forward to my stay during my next visit to Chicago!"
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,190
    CA $853
    per traveller
    found 21 hours ago
    The Emily Hotel
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Jan 7 - Jan 11

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,044
    CA $760
    per traveller
    found 21 hours ago
    Level Chicago Fulton Market

Historic Route 66 Hotel Deals

A canyon landscape with layered rock formations.

Ramada by Wyndham Williams/Grand Canyon Area

Ramada by Wyndham Williams/Grand Canyon Area
3.0 star property
1,227.1 km from Historic Route 66
7.8 out of 10, Good, (1,005 reviews)
"Older hotel that needs updating. Rooms and bathrooms are old. Paint, carpet, and bathroom were dirty and dingy. Staff not friendly in the early morning."
The price is CA $84
CA $99 total
includes taxes & fees
Nov 9 - Nov 10
Ramada by Wyndham Williams/Grand Canyon Area
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.
See all properties in Historic Route 66

Frequently Asked Questions

How much does a Historic Route 66 vacation package cost?

Our Historic Route 66 packages, which start at just CA $758, 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.