Title: Ski Vacations in Great River Road 2026 | Expedia.ca ![](https://images.trvl-media.com/place/7956/10192ec4-1419-451d-9e2e-50909ca12beb.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Great River Road 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 Great River Road 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 $708 per person Feb 20 - Feb 24 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Fantastic breakfast!!! Reviewed on Jan 18, 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $1,180 per person Feb 27 - Mar 5 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Nice newer hotel with lots of options. Rooms are a bit industrial but fine, nothing super luxurious but adequate. Reviewed on Jan 16, 2026 ![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 $1,134 per person Feb 27 - Mar 5 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on Jan 8, 2026 ![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 $1,055 per person Feb 27 - Mar 5 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (380 reviews) I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay. Reviewed on Jan 12, 2026 ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Virgin Hotels Chicago Downtown Chicago CA $988 per person Feb 27 - Mar 5 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (1,404 reviews) The sweetest staff ever! Very welcoming. Had a great stay! Reviewed on Jan 9, 2026 Don't see what you're looking for? See all available trips from Columbus to Great River Road [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-18/2026-02-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MSP&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Great River Road 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 $1,125 per person Mar 26 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing Reviewed on Jan 13, 2026 ![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 $1,460 per person Mar 26 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return. Reviewed on Jan 5, 2026 ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,315 per person Mar 26 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Yes didn’t know you get free breakfast Reviewed on Jan 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Great River Road [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-18/2026-02-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MSP&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in Great River Road 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 $705 per person Mar 26 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Fantastic breakfast!!! Reviewed on Jan 18, 2026 ![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 $1,125 per person Mar 26 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing Reviewed on Jan 13, 2026 ![Hilton New Orleans Riverside](https://images.trvl-media.com/lodging/1000000/20000/19800/19716/w3837h2558x3y3-99d26293_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton New Orleans Riverside New Orleans Central Business District CA $1,133 per person Apr 9 - Apr 12 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to New Orleans (MSY) 8.8/10 Excellent! (1,142 reviews) All is perfect thanks Reviewed on Jan 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Great River Road [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-18/2026-02-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MSP&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Great River Road 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 $708 per person Feb 20 - Feb 24 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Fantastic breakfast!!! Reviewed on Jan 18, 2026 ![Hilton New Orleans Riverside](https://images.trvl-media.com/lodging/1000000/20000/19800/19716/w3837h2558x3y3-99d26293_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton New Orleans Riverside New Orleans Central Business District CA $1,046 per person Feb 25 - Mar 1 just found Roundtrip flight included Toronto (YYZ) to New Orleans (MSY) 8.8/10 Excellent! (1,142 reviews) All is perfect thanks Reviewed on Jan 17, 2026 ![Emery, Autograph Collection Hotel](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169421/99252703_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Emery, Autograph Collection Hotel Downtown Minneapolis CA $1,387 per person Apr 7 - Apr 11 found 7 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Minneapolis (MSP) 9.4/10 Exceptional! (628 reviews) Room was almost spotless; shower floor was a little dirty as well as the bathroom floor. Over all the room was great! Don’t use too much of the soap though; that will cost extra. Next time I will bring my own. Reviewed on Dec 30, 2025 Don't see what you're looking for? See all available trips from Columbus to Great River Road [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-18/2026-02-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MSP&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in Great River Road #### What are some benefits when booking ski vacations in Great River Road? 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 Great River Road? 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 Great River Road, 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 Great River Road with some as cheap as CA $705\. 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 Great River Road. 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 33 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 Great River Road. #### Can I book all-inclusive ski vacations in Great River Road? 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 Great River Road 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 Great River Road'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 Great River Road? 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 Great River Road. 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 33\. 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 Great River Road ](https://expedia.ca/Cheap-Flights-To-Great-River-Road.d702655377080487936.Travel-Guide-Flights)[ Great River Road Hotels ](https://expedia.ca/Great-River-Road-Hotels.d702655377080487936.Travel-Guide-Hotels)[ Great River Road Vacation Rentals ](https://expedia.ca/Great-River-Road-Vacation-Rentals.d702655377080487936.Travel-Guide-VacationRentals)[ Great River Road Car Rentals ](https://expedia.ca/Car-Rentals-In-Great-River-Road.d702655377080487936.Car-Rental-Guide)[ Great River Road Vacations ](https://expedia.ca/Great-River-Road.d702655377080487936.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