North Pullman Ski Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

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

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

Flight and Ski hotel deals in North Pullman

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $811
per person
Oct 28 - Oct 30
found 23 hours ago
Roundtrip flight included
Montreal (YMQ) 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

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,501
per person
Oct 19 - Oct 23
found 21 hours 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

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,186
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Honestly, nothing special for the price they command. Unfortunately, all the hotels there are gouging these days. Obviously, all about the location - can’t beat that.

Reviewed on Aug 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $905
per person
Oct 28 - Oct 30
found 23 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Great staff great location

Reviewed on Aug 16, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Downtown Chicago
CA $1,843
per person
Oct 11 - Oct 15
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,384 reviews)
Nice hotel in a great location. Room was clean and quiet but like a lot of things it’s the small things that make a hotel great. Here’s what I found: 1. The coffee in the room is just a small cup of espresso for 2. 2. No coffee bar in the lobby or any place at all to grab a large cup and take back to the room. 3. The lobby and public areas are so over air conditioned one has to wear a jacket in the heat of summer. This goes for the casual restaurant on the ground floor. When we could we ate outside. 4. The gym is nice but has minimal equipment even though there is room for a few machines. When I return to Chicago I’ll probably try a different hotel but I wouldn’t be opposed to staying at the Thompson again.

Reviewed on Aug 16, 2026

Don't see what you're looking for?
See all available trips from Columbus to North Pullman
View all trips

5* Ski holidays in North Pullman

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 6 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

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $4,051
per person
Sep 16 - Sep 21
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

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
CA $3,277
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Don't see what you're looking for?
See all available trips from Columbus to North Pullman
View all trips

3 Night Ski holidays in North Pullman

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $999
per person
Nov 3 - Nov 6
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in. 4 days later, the on-line booking co. Said the manager did not agree to release my reservation. Unethical procedurers.

Reviewed on Aug 12, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,186
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Honestly, nothing special for the price they command. Unfortunately, all the hotels there are gouging these days. Obviously, all about the location - can’t beat that.

Reviewed on Aug 16, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,388
per person
Oct 4 - Oct 7
found 1 day 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

Don't see what you're looking for?
See all available trips from Columbus to North Pullman
View all trips

4 Night Ski holidays in North Pullman

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,236
per person
Oct 19 - Oct 23
found 21 hours 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

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,418
per person
Sep 28 - Oct 2
found 3 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

The Emily Hotel

The Emily Hotel

Downtown Chicago
CA $1,860
per person
Oct 11 - Oct 15
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,335 reviews)
We were there for a wedding this weekend and the Emily hotel was absolutely stunning! The bar happy hour was a lot of fun and Sean our server was amazing. The hotel is beautiful and was immaculate.

Reviewed on Aug 16, 2026

Don't see what you're looking for?
See all available trips from Columbus to North Pullman
View all trips

Plan the ultimate ski vacation in North Pullman

What are some benefits when booking ski vacations in North Pullman?

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 North Pullman?

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 North Pullman, 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 North Pullman with some as cheap as CA $811. 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 North Pullman. 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 21 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 North Pullman.

Can I book all-inclusive ski vacations in North Pullman?

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 North Pullman 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 North Pullman'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 North Pullman?

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 North Pullman. 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 21. With Expedia Rewards, you can earn points towards your next booking.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in North Pullman

More vacations you might like

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