Title: Ski Vacations in Chicago 2026 | Expedia.ca ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago 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 Chicago Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Lisle Naperville](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/8f0b88a7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Lisle Naperville CA $444 per person Jan 18 - Jan 20 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 7.8/10 Good! (1,192 reviews) Dirty sheets, old room. Reviewed on Dec 12, 2025 ![The Westin Chicago Lombard](https://images.trvl-media.com/lodging/2000000/1700000/1690600/1690548/ef211bfd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Chicago Lombard CA $1,440 per person Feb 20 - Feb 27 found 1 day ago Roundtrip flight included Abbotsford (YXX) to Chicago (ORD) 8.8/10 Excellent! (1,128 reviews) Room was great. Restaurant was bad. Service was terrible. Don’t eat there. Reviewed on Dec 14, 2025 ![Renaissance Schaumburg Convention Center Hotel](https://images.trvl-media.com/lodging/2000000/1490000/1485600/1485559/7a423870_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Renaissance Schaumburg Convention Center Hotel CA $1,100 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,000 reviews) The tv inside of the bathroom mirror Reviewed on Dec 14, 2025 ![Lincolnshire Marriott Resort](https://images.trvl-media.com/lodging/1000000/30000/23100/23049/edaa8813_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lincolnshire Marriott Resort Half Day CA $1,298 per person Jan 31 - Feb 3 found 1 day ago Roundtrip flight included Abbotsford (YXX) to Chicago (ORD) 8.8/10 Excellent! (1,001 reviews) The hotel is dated and the check in staff were not very friendly. Reviewed on Nov 28, 2025 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Lisle Naperville](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/8f0b88a7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Lisle Naperville CA $482 per person Jan 30 - Feb 2 found 22 hours ago Roundtrip flight included Detroit (DTW) to Chicago (ORD) 7.8/10 Good! (1,192 reviews) Dirty sheets, old room. Reviewed on Dec 12, 2025 ![Renaissance Schaumburg Convention Center Hotel](https://images.trvl-media.com/lodging/2000000/1490000/1485600/1485559/7a423870_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Renaissance Schaumburg Convention Center Hotel CA $938 per person Feb 13 - Feb 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,000 reviews) The tv inside of the bathroom mirror Reviewed on Dec 14, 2025 ![The Westin Chicago Lombard](https://images.trvl-media.com/lodging/2000000/1700000/1690600/1690548/ef211bfd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Chicago Lombard CA $704 per person Feb 5 - Feb 8 found 2 hours ago Roundtrip flight included Grande Prairie (YQU) to Chicago (ORD) 8.8/10 Excellent! (1,128 reviews) Room was great. Restaurant was bad. Service was terrible. Don’t eat there. Reviewed on Dec 14, 2025 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Lisle Naperville](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/8f0b88a7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Lisle Naperville CA $470 per person Feb 9 - Feb 13 found 1 day ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 7.8/10 Good! (1,192 reviews) Dirty sheets, old room. Reviewed on Dec 12, 2025 ![Quality Inn Bolingbrook I-55](https://images.trvl-media.com/lodging/1000000/800000/793500/793472/c138d907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quality Inn Bolingbrook I-55 CA $476 per person Feb 9 - Feb 13 found 1 day ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 8.4/10 Very Good! (1,000 reviews) It was great and the staff was so helpful and kind the lady that checked me in was awesome and I left my key in my room the guy that got me another one verified who I was quickly and made me another key then when I checked out the guy was really nice Reviewed on Dec 15, 2025 ![The Westin Chicago Lombard](https://images.trvl-media.com/lodging/2000000/1700000/1690600/1690548/ef211bfd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Chicago Lombard CA $626 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,128 reviews) Room was great. Restaurant was bad. Service was terrible. Don’t eat there. Reviewed on Dec 14, 2025 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in Chicago #### What are some benefits when booking ski vacations in Chicago? 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 Chicago? 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 Chicago, 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 Chicago with some as cheap as CA $444\. 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 Chicago. 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 10 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 Chicago. #### Can I book all-inclusive ski vacations in Chicago? 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 Chicago 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 Chicago'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 Chicago? 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 Chicago. 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 10\. With Expedia Rewards, you can earn points towards your next booking. ## Ski Hotels in Chicago ![Victorian Rose Garden](https://images.trvl-media.com/lodging/4000000/3740000/3733900/3733857/e60f0980_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Victorian Rose Garden 314 Washington Street Algonquin IL - 1 hour drive from Michigan Avenue Stay at this B&B in Algonquin. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Buffalo Park Forest Preserve and Algonquin Lakes Trailhead ... 9.8/10 Exceptional! (90 reviews) The space was beautiful and Sherry was the sweetest hostess! We loved every minute of our stay! Reviewed on Oct 30, 2025 [](https://expedia.ca/Algonquin-Hotels-Victorian-Rose-Garden.h3733857.Hotel-Information) ![Hyatt Regency Lisle near Naperville](https://images.trvl-media.com/lodging/1000000/20000/13300/13266/0173b9c9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Lisle near Naperville 1400 Corporetum Drive Lisle IL - 43 min drive from Michigan Avenue Book a stay at this business-friendly hotel in Lisle. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ... 7.6/10 Good! (1,059 reviews) Courteous staff, cleanliness of lobby Reviewed on Dec 14, 2025 [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Lisle-Near-Naperville.h13266.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG](https://images.trvl-media.com/lodging/1000000/660000/658500/658492/96d51c6b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG 2595 Bunker Hill Dr Algonquin IL - 1 hour drive from Michigan Avenue Book a stay at this business-friendly hotel in Algonquin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ... 8/10 Very Good! (1,001 reviews) After renewal . The price is matched to the room Reviewed on Dec 2, 2025 [](https://expedia.ca/Algonquin-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Algonquin.h658492.Hotel-Information) [See all 5,618 properties in Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=178248) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## 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 Chicago ](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[ Chicago Hotels ](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[ Chicago Vacation Rentals ](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[ Chicago Car Rentals ](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[ Chicago Vacations ](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides)[ Things to do in Chicago ](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) \* 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