Ski Vacations in Historic Route 66 2026

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Flight and Ski hotel deals in Historic Route 66

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

Level Chicago – Old Town

Downtown Chicago

CA $1,152

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy

Reviewed on Aug 19, 2026

Four Seasons Hotel Chicago

Downtown Chicago

CA $6,031

per person

Oct 7 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around

Reviewed on Aug 16, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,393

per person

Oct 27 - Oct 31

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

L7 Chicago by LOTTE

Downtown Chicago

CA $2,762

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (4,495 reviews)

Coffee in lobby was good amenity . Valet were super nice and helpful. Breakfast was amazing

Reviewed on Aug 20, 2026

Silversmith Hotel Chicago Downtown

Downtown Chicago

CA $3,130

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (2,348 reviews)

Great receptionist. Very helpful. George who waited on me at breakfast is a gem. What a lovely man and a credit to the hotel. Lobby and reception are very modern and nice. Rooms are dated with old furniture and VERY dark. No decent lighting and you need a lot of strength just to open or close curtains. Location is fabulous.

Reviewed on Aug 20, 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

Downtown Chicago

CA $1,674

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

A+

Reviewed on Aug 20, 2026

Four Seasons Hotel Chicago

Downtown Chicago

CA $6,031

per person

Oct 7 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Reviewed on Aug 16, 2026

La Posada de Santa Fe, A Tribute Portfolio Resort & Spa by Marriott

Historic Eastside

CA $3,053

per person

Sep 21 - Sep 28

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Albuquerque (ABQ)

8.2/10 Very good! (1,004 reviews)

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3 Night Ski holidays in Historic Route 66

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

Level Chicago – Old Town

Downtown Chicago

CA $1,152

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy

Reviewed on Aug 19, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,275

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Swissotel - Chicago

Downtown Chicago

CA $1,207

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,537 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

Downtown Chicago

CA $1,279

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,589

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Level Chicago Fulton Market

Downtown Chicago

CA $1,393

per person

Oct 27 - Oct 31

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

Reviewed on Aug 17, 2026

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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 $1,152. 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 29 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 29. With Expedia Rewards, you can earn points towards your next booking.