Title: West Side Ski Holidays 2026/2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/829/ad657303-bbed-4f45-9ba5-b7c23d3e76f3.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # West Side Ski Holidays ## Book a Ski Hotel + Flight or Car together to unlock savings Photo by throwingsofas - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ## Top flight + Ski hotel deals in West Side 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 Save 100% on your flight £189 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on 22 Nov 2025 ![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 Save 100% on your flight £363 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on 26 Nov 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 Save 100% on your flight £262 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on 3 Dec 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 Save 100% on your flight £383 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on 2 Dec 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 Save 100% on your flight £228 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) 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 4 Dec 2025 Don't see what you're looking for? See all available trips from Charlotte to West Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in West Side Price found within the past 48 hours. Click for updated prices. ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago Save 100% on your flight £335 per person 27 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on 26 Nov 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 Save 100% on your flight £383 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on 2 Dec 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 Save 100% on your flight £545 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on 29 Nov 2025 Don't see what you're looking for? See all available trips from Charlotte to West Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in West Side Price found within the past 48 hours. Click for updated prices. ![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 Save 100% on your flight £262 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on 3 Dec 2025 ![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 Save 100% on your flight £363 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on 26 Nov 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 Save 100% on your flight £383 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on 2 Dec 2025 Don't see what you're looking for? See all available trips from Charlotte to West Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in West Side 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 £1,163 per person 7 Feb - 11 Feb found 1 day ago Return direct flight included London (LHR) 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 26 Nov 2025 ![Chicago luxury home suites](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/740de96f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago luxury home suites Downtown Chicago Save 100% on your flight £1,602 per person 13 Jan - 17 Jan found 9 hours ago Return direct flight included London (LON) to Chicago (ORD) 10/10 Exceptional! (1 review) Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job. Reviewed on 26 Nov 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 £1,187 per person 13 Jan - 17 Jan found 9 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on 29 Nov 2025 Don't see what you're looking for? See all available trips from London to West Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your West Side ski holiday #### How can I book the best ski holiday to West Side in 2026/2026? Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in West Side. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties. #### How can I find cheap West Side ski holidays? Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book West Side accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from £189\. Prices and availability are subject to change. Additional terms may apply. #### Can I book last-minute ski holidays to West Side? Use our handy last-minute deals page to look for ski holidays to West Side at a steal. If your dates are fixed, simply input the details and see what specials are available. #### What should I consider when booking family ski holidays in West Side? West Side is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks. #### Can I book all-inclusive ski holidays to West Side? All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in West Side. If not, consider booking your flights and accommodation together to save money that way instead. #### When's the best time of year to plan a ski trip to West Side? Ski season in West Side generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter. #### How can I find the best deals on West Side ski holiday packages? If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining. #### Can I book a West Side ski trip with free cancellation and/or flexible dates? If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in West Side that offer it. #### Why should I book a ski holiday package in West Side with Expedia? Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday. ## More holidays 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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Top Ski Holiday Destinations > - [Ski Holidays in Andorra ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/4/Andorra) > - [Ski Holidays in Austria ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/11/Austria) > - [Ski Holidays in Borovets ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/602265/Borovets) > - [Ski Holidays in Bulgaria ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/26/Bulgaria) > - [Ski Holidays in Canada ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/31/Canada) > - [Ski Holidays in Chamonix ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/6050949/Chamonix-Mont-Blanc) > - [Ski Holidays in Finland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/58/Finland) > - [Ski Holidays in France ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/59/France) > - [Ski Holidays in Italy ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/86/Italy) > - [Ski Holidays in Japan ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/89/Japan) > - [Ski Holidays in Meribel ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/8725/Meribel) > - [Ski Holidays in Norway ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/138/Norway) > - [Ski Holidays in Poland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/146/Poland) > - [Ski Holidays in Scotland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/11219/Scotland) > - [Ski Holidays in St-Anton ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/5828/Sankt-Anton-Am-Arlberg) > - [Ski Holidays in Sweden ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/173/Sweden) > - [Ski Holidays in Switzerland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/174/Switzerland) > - [Ski Holidays in Tignes ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/184273/Tignes) > - [Ski Holidays in Val-D'isere ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/10259/Val-DIsere) ## More Holiday Ideas [Flights to West Side ](https://expedia.co.uk/Cheap-Flights-To-West-Side.d553248635976475400.Travel-Guide-Flights)[ West Side Hotels ](https://expedia.co.uk/West-Side-Hotels.d553248635976475400.Travel-Guide-Hotels)[ West Side Holiday Rentals ](https://expedia.co.uk/West-Side-Holiday-Rentals.d553248635976475400.Travel-Guide-HolidayRentals)[ West Side Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-West-Side.d553248635976475400.Car-Hire-Guide)[ West Side Holidays ](https://expedia.co.uk/West-Side.d553248635976475400.Holidays-City-Breaks)[ Things to do in West Side ](https://expedia.co.uk/Things-To-Do-In-West-Side.d553248635976475400.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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