Ski Vacations in Rush Street 2026

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Flight and Ski hotel deals in Rush Street

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

Level Chicago – Old Town

Downtown Chicago

CA $818

per person

Oct 5 - Oct 7

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

Swissotel - Chicago

Downtown Chicago

CA $1,132

per person

Oct 22 - Oct 25

found 4 hours ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.

Reviewed on Aug 17, 2026

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

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

Thompson Chicago, by Hyatt

Downtown Chicago

CA $1,843

per person

Oct 11 - Oct 15

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,384 reviews)

Broken elevator causing long lines and delays. Coffee set up in the lobby was awkward and $4 for a cup. Friends found bed bug in their bed. Staff very nice and good location.

Reviewed on Aug 16, 2026

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5* Ski holidays in Rush Street

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

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,992

per person

Sep 28 - Oct 2

found 11 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

Downtown Chicago

CA $2,371

per person

Oct 29 - Nov 2

found 14 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

The Langham, Chicago

Downtown Chicago

CA $2,996

per person

Sep 28 - Oct 2

found 11 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.8/10 Exceptional! (1,002 reviews)

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3 Night Ski holidays in Rush Street

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

Swissotel - Chicago

Downtown Chicago

CA $1,132

per person

Oct 22 - Oct 25

found 4 hours ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Reviewed on Aug 17, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,287

per person

Oct 22 - Oct 25

found 4 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

Downtown Chicago

CA $1,293

per person

Sep 20 - Sep 23

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,145 reviews)

The Pendry was in an exceptional location. The bell staff were phenomenal, they were both courteous and helpful. The only frustration with our stay was the elevator situation. One elevator wasn’t working and there were very long waits for the other two and they were often full by the time it came to our floor.

Reviewed on Aug 16, 2026

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4 Night Ski holidays in Rush Street

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

Swissotel - Chicago

Downtown Chicago

CA $1,322

per person

Sep 24 - Sep 28

found 9 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Reviewed on Aug 17, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,418

per person

Sep 28 - Oct 2

found 8 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

Reviewed on Aug 12, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,711

per person

Oct 11 - Oct 15

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Reviewed on Aug 15, 2026

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What are some benefits when booking ski vacations in Rush Street?

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 Rush Street?

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 Rush Street, 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 Rush Street with some as cheap as CA $818. 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 Rush Street. 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 22 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 Rush Street.

Can I book all-inclusive ski vacations in Rush Street?

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 Rush Street 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 Rush Street'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 Rush Street?

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 Rush Street. 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 22. With Expedia Rewards, you can earn points towards your next booking.