Title: Ski Vacations in Far Southwest Side 2026 | Expedia.ca ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southwest Side Ski Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $888 per person Apr 17 - Apr 20 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everyone that we encountered at the hotel was so helpful and so nice. Reviewed on Mar 11, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago CA $2,248 per person Jun 3 - Jun 9 found 15 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (3,613 reviews) Clean room, perfect location Reviewed on Mar 11, 2026 ![Hotel Arista](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141763/a6c36a1d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Arista CA $946 per person May 24 - May 29 found 16 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.4/10 Exceptional! (1,007 reviews) Room was clean, staff was friendly and parking was really easy. Very comfortable stay. Reviewed on Mar 5, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $2,203 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (414 reviews) This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back. Reviewed on Mar 8, 2026 ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/d267fd21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago CA $2,079 per person Jun 3 - Jun 9 found 15 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (1,326 reviews) Room was nice and clean, decent view. Perfect location. Close to shopping and nice restaurants. Staff was amazing; Myron in particular was so kind and accommodating. Reviewed on Mar 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-11/2026-04-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,542 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,004 reviews) Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again. Reviewed on Mar 1, 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $2,022 per person May 1 - May 4 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) This is an amazing hotel. From the facilities to the staff, the food and atmosphere and the intricacies of the room itself it’s an amazing property. In the heart of what used to be “The magnificent mile” it’s unimposing from the exterior but once you step inside the place is special. If you can afford it it’s probably the best hotel in Chicago. Do yourself a favor and splurge a little on a weekend trip. Chicago is a wonderful city for food and drinks. It’s seen better days but still a beautiful city. Reviewed on Mar 10, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,644 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,839 reviews) One of the best hotels I've ever stayed at Reviewed on Mar 10, 2026 Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-11/2026-04-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $888 per person Apr 17 - Apr 20 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everyone that we encountered at the hotel was so helpful and so nice. Reviewed on Mar 11, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $2,203 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (414 reviews) This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back. Reviewed on Mar 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-11/2026-04-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $782 per person Apr 26 - Apr 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everyone that we encountered at the hotel was so helpful and so nice. Reviewed on Mar 11, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,161 per person May 13 - May 17 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (414 reviews) This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back. Reviewed on Mar 8, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/46b44b35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $1,227 per person May 14 - May 18 found 16 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (858 reviews) I would stay here again without a second thought. Great Reviewed on Mar 11, 2026 Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-11/2026-04-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in Far Southwest Side #### What are some benefits when booking ski vacations in Far Southwest Side? 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 Far Southwest Side? 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 Far Southwest Side, 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 Far Southwest Side with some as cheap as CA $782\. 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 Far Southwest Side. 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 31 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 Far Southwest Side. #### Can I book all-inclusive ski vacations in Far Southwest Side? 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 Far Southwest Side 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 Far Southwest Side'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 Far Southwest Side? 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 Far Southwest Side. 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 31\. With Expedia Rewards, you can earn points towards your next booking. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Ski Vacation Destinations > - [Ski vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4115/Whistler) > - [Ski vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4332/Banff) > - [Ski vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/55374/Mont-Tremblant) > - [Ski vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/8028/Jasper) > - [Ski vacations in Jackson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180006/Jackson) > - [Ski vacations in France ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/59/France) > - [Ski vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180017/Quebec) > - [Ski vacations in Queenstown ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3611/Queenstown) > - [Ski vacations in Lake Louise ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/10115/Lake-Louise) > - [Ski vacations in Nelson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6194600/Nelson) > - [Ski vacations in Kitzbuhel ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6346453/Kitzbuehel) > - [Ski vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/174/Switzerland) > - [Ski vacations in La Plagne ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6034464/La-Plagne) > - [Ski vacations in St Gervais ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3000402612/St-Gervais-Sur-Mare) > - [Ski vacations in Austria ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/11/Austria) > - [Ski vacations in Germany ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/64/Germany) > - [Ski vacations in Wengen ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6186871/Wengen) > - [Ski vacations in Ontario ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/2680/Ontario) > - [Ski vacations in Colorado ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/207/Colorado) ## More Vacations Ideas [Flights to Far Southwest Side ](https://expedia.ca/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[ Far Southwest Side Hotels ](https://expedia.ca/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[ Far Southwest Side Vacation Rentals ](https://expedia.ca/Far-Southwest-Side-Vacation-Rentals.d553248635976475353.Travel-Guide-VacationRentals)[ Far Southwest Side Car Rentals ](https://expedia.ca/Car-Rentals-In-Far-Southwest-Side.d553248635976475353.Car-Rental-Guide)[ Far Southwest Side Vacations ](https://expedia.ca/Far-Southwest-Side.d553248635976475353.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app