Title: West Side Ski Holidays 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. ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston £511 per person 27 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) I would stay here again if I need to stay in Evanston again. Thanks Reviewed on 19 Jan 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 £1,211 per person 15 Mar - 19 Mar found 16 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on 20 Jan 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 £617 per person 27 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on 18 Jan 2026 ![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 £915 per person 15 Mar - 19 Mar found 16 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all. Reviewed on 20 Jan 2026 ![Viceroy Chicago](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/3aeed14b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Viceroy Chicago Downtown Chicago £1,064 per person 2 Apr - 7 Apr found 3 hours ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (1,129 reviews) Boutique with a heavy sprinkle of luxury... that’s how I'd describe my stay at Viceroy Chicago. The rooms are spacious, the bathroom was a great size, and the bed gave me a perfect night's sleep. I loved the mood lighting presets for setting the vibe and the fact that the TV was Chromecast enabled. For drinks, the lush and botanical Pandan felt properly elevated with divine South Asian bites and finesse. I did hit Somerset for brunch; while the quality was fine, it was just 'OK' for me. Major bonus: Since I booked through Expedia, I snagged an automatic 25% off all food and beverages (before tip) at checkout. That’s a nice little perk to have! The location is unbeatable. Very walkable to high-end shopping, and Ubers literally match and arrive in 1–3 minutes. 100% recommend a short stay here, and I’m definitely coming back for that rooftop pool in the warmer months! Reviewed on 20 Jan 2026 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/2026-02-21/2026-02-28/?FromAirport=LHR&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. ![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 £1,211 per person 15 Mar - 19 Mar found 16 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on 20 Jan 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 £2,768 per person 11 Apr - 17 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on 20 Jan 2026 ![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 £3,077 per person 11 Apr - 17 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room. Reviewed on 11 Jan 2026 Don't see what you're looking for? See all available trips from Edinburgh to West Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-21/2026-02-28/?FromAirport=EDI&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. ![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 £726 per person 2 Mar - 5 Mar found 5 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all. Reviewed on 20 Jan 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 £895 per person 2 Mar - 5 Mar found 5 hours ago Return flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often. Reviewed on 20 Jan 2026 ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago £861 per person 2 Mar - 5 Mar found 5 hours ago Return flight included London (LON) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Great staff that paid attention quickly to concerns. Reviewed on 19 Jan 2026 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/2026-02-21/2026-02-28/?FromAirport=LON&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. ![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 £617 per person 27 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on 18 Jan 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 £1,211 per person 15 Mar - 19 Mar found 16 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on 20 Jan 2026 ![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 £915 per person 15 Mar - 19 Mar found 16 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all. Reviewed on 20 Jan 2026 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/2026-02-21/2026-02-28/?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 2026/2027? 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 £511\. 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 > - 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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