Historic Route 66 Ski Vacations

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Flight and Ski hotel deals in Historic Route 66

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

Hotel Riu Plaza Chicago

Downtown Chicago
CA $905
per person
Oct 28 - Oct 30
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on Aug 17, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,132
per person
Oct 22 - Oct 25
found 12 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,501
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

The Hacienda & Spa at Hotel Santa Fe

The Hacienda & Spa at Hotel Santa Fe

Downtown Santa Fe
CA $1,688
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albuquerque (ABQ)
9.4/10 Exceptional! (1,000 reviews)
Excellent location

Reviewed on Jul 15, 2026

Quail Run

Quail Run

Arroyo Chamisa
CA $2,089
per person
Sep 23 - Sep 30
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albuquerque (ABQ)
10/10 Exceptional! (2 reviews)
This was a resort property that had a restaurant /dining room that had awesome food and reasonable prices. It was quite convenient. The maintenance office was very responsive to a problem we had initially with the AC. Laurie (Lorrie?) was super helpful. The unit we rented (312) had an underground garage parking spot right next to the elevator. Also very convenient. The unit itself had every amenity you could want including a full Xfinity TV cable lineup. The report also has an executive golf course with very reasonable rates for vacationers to play. My only complaint (very minor) was that there was not really a separate bedroom TV. There was a monitor that you could watch whatever the person in the living room was watching...but no way to get separate channels.. Overall I highly recommend this resort to anyone who wants a comfortable resort-style experience in Santa Fe.

Reviewed on May 24, 2026

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5* Ski holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,992
per person
Sep 28 - Oct 2
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on Aug 16, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
CA $2,371
per person
Oct 29 - Nov 2
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Rosewood Inn of the Anasazi

Rosewood Inn of the Anasazi

Downtown Santa Fe
CA $3,045
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albuquerque (ABQ)
9.6/10 Exceptional! (912 reviews)
The service and the caliber of the guestrooms was remarkable. And I don’t say that lightly. Between the turndown service and the mid morning check-in, our room was always clean —& up to snuff. I also appreciated the warm response of all the hotel stuff from when I needed to borrow two umbrellas to getting my car out of valet parking. It was such a wonderful experience and the location is phenomenal. Exactly what my partner and I were looking for.

Reviewed on Jul 30, 2026

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3 Night Ski holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,132
per person
Oct 22 - Oct 25
found 12 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,287
per person
Oct 22 - Oct 25
found 12 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on Aug 17, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,293
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,145 reviews)
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4 Night Ski holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,322
per person
Sep 24 - Sep 28
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,418
per person
Sep 28 - Oct 2
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,711
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
The property seems new and well kept. There are many amenities that enhance the stay including a pool, hot tub, basketball ball court, game room, sauna and steam room. We loved our stay. Only negatives were there was not an ice machine, there was not daily cleaning service, the towels were OK and we needed our trash emptied but were many sure how to request that. Overall a great spot. Affordable and lots of space with great views!

Reviewed on Aug 15, 2026

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Plan the ultimate ski vacation in Historic Route 66

What are some benefits when booking ski vacations in Historic Route 66?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Historic Route 66?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Historic Route 66, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Historic Route 66 with some as cheap as CA $905. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Historic Route 66. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 23 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Historic Route 66.

Can I book all-inclusive ski vacations in Historic Route 66?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Historic Route 66 in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Historic Route 66's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Historic Route 66?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Historic Route 66. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 23. With Expedia Rewards, you can earn points towards your next booking.

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