Title: Ski Vacations in South Suburbs 2026 | Expedia.ca ![](https://images.trvl-media.com/place/55204/1a24b950-2953-4f3d-aa54-9c3ba43291ed.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Suburbs Ski Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Steve Ignowski - ## 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 South Suburbs Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $442 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on Dec 8, 2025 ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Swissotel - Chicago Downtown Chicago CA $483 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (2,947 reviews) Clean property and room with a nice view, all staff members were polite and helpful when needed Reviewed on Dec 12, 2025 ![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago Athletic Association, a Hyatt Hotel Downtown Chicago CA $549 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,002 reviews) Amazing location. Love this historic hotel and the included room service breakfast is one of the best I’ve ever had. Reviewed on Dec 8, 2025 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $514 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7\. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience. Reviewed on Dec 9, 2025 ![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 $538 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Room was clean and staff members were super friendly Reviewed on Dec 12, 2025 Don't see what you're looking for? See all available trips from Columbus to South Suburbs [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-13/2026-01-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in South Suburbs Price found within the past 48 hours. Click for updated prices. ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $900 per person Jan 21 - Jan 24 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted. Reviewed on Dec 11, 2025 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,065 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on Dec 3, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,201 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on Nov 29, 2025 Don't see what you're looking for? See all available trips from Columbus to South Suburbs [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-13/2026-01-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in South Suburbs Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $442 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on Dec 8, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $853 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted. Reviewed on Dec 11, 2025 ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Swissotel - Chicago Downtown Chicago CA $483 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (2,947 reviews) Clean property and room with a nice view, all staff members were polite and helpful when needed Reviewed on Dec 12, 2025 Don't see what you're looking for? See all available trips from Columbus to South Suburbs [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-13/2026-01-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in South Suburbs Price found within the past 48 hours. Click for updated prices. ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $809 per person Jan 26 - Jan 30 found 16 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on Nov 26, 2025 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $877 per person Jan 26 - Jan 30 found 16 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside Reviewed on Dec 4, 2025 ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $814 per person Jan 26 - Jan 30 found 16 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on Dec 8, 2025 Don't see what you're looking for? See all available trips from Columbus to South Suburbs [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-13/2026-01-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in South Suburbs #### What are some benefits when booking ski vacations in South Suburbs? 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 South Suburbs? 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 South Suburbs, 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 South Suburbs with some as cheap as CA $442\. 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 South Suburbs. 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 36 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 South Suburbs. #### Can I book all-inclusive ski vacations in South Suburbs? 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 South Suburbs 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 South Suburbs'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 South Suburbs? 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 South Suburbs. 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 36\. 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 South Suburbs ](https://expedia.ca/Cheap-Flights-To-South-Suburbs.d6264251.Travel-Guide-Flights)[ South Suburbs Hotels ](https://expedia.ca/South-Suburbs-Hotels.d6264251.Travel-Guide-Hotels)[ South Suburbs Vacation Rentals ](https://expedia.ca/South-Suburbs-Vacation-Rentals.d6264251.Travel-Guide-VacationRentals)[ South Suburbs Car Rentals ](https://expedia.ca/Car-Rentals-In-South-Suburbs.d6264251.Car-Rental-Guide)[ South Suburbs Vacations ](https://expedia.ca/South-Suburbs.d6264251.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