Title: Chicago Ski Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago Ski Holidays ## Book a Ski Hotel + Flight or Car together to unlock savings - ## 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 Chicago Price found within the past 48 hours. Click for updated prices. ![Lincolnshire Marriott Resort](https://images.trvl-media.com/lodging/1000000/30000/23100/23049/1efbe75c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lincolnshire Marriott Resort Half Day £761 per person 2 May - 4 May found 1 day ago Return flight included London (LHR) to Chicago (ORD) 8.8/10 Excellent! (1,003 reviews) Excellent room, dining was very nice (great apply, walnut and beet salad at the restaurant and great beer options), nice and attentive staff. Could grab a water downstairs at any time and the options to find a space to hang with a colleague to chat were ample. Reviewed on 22 Mar 2026 Don't see what you're looking for? See all available trips from London to Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-28/2026-05-05/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your Chicago ski holiday #### How can I book the best ski holiday to Chicago in 2026/2027? Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Chicago. 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 Chicago ski holidays? Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Chicago 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 £761\. Prices and availability are subject to change. Additional terms may apply. #### Can I book last-minute ski holidays to Chicago? Use our handy last-minute deals page to look for ski holidays to Chicago 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 Chicago? Chicago 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 Chicago? All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Chicago. 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 Chicago? Ski season in Chicago 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 Chicago 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 Chicago 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 Chicago that offer it. #### Why should I book a ski holiday package in Chicago 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. ## Top Ski Chicago Hotels ![Victorian Rose Garden](https://images.trvl-media.com/lodging/4000000/3740000/3733900/3733857/c43a96d0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Victorian Rose Garden 314 Washington Street Algonquin IL - 51 min drive from Wrigley Field Stay at this B&B in Algonquin. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Buffalo Park Forest Preserve and Algonquin Lakes Trailhead ... 9.4/10 Exceptional! (290 reviews) The space was beautiful and Sherry was the sweetest hostess! We loved every minute of our stay! Reviewed on 30 Oct 2025 [](https://expedia.co.uk/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 Wrigley Field Stay at this business-friendly hotel in Lisle. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ... 7.6/10 Good! (1,123 reviews) It rained and leaked everywhere. Into the room and the lobby was flooded. They told me i had to switch rooms. Building engineer handed me a key and left. No help in moving my stuff. Reviewed on 23 Mar 2026 [](https://expedia.co.uk/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/b0493e70_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG 2595 Bunker Hill Dr Algonquin IL - 53 min drive from Wrigley Field Stay at this business-friendly hotel in Algonquin. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ... 8.2/10 Very Good! (1,000 reviews) Clean with nice staff Reviewed on 24 Mar 2026 [](https://expedia.co.uk/Algonquin-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Algonquin.h658492.Hotel-Information) [See all 5,513 properties in Chicago](https://expedia.co.uk/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 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 Chicago ](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[ Chicago Hotels ](https://expedia.co.uk/Chicago-Hotels.d178248.Travel-Guide-Hotels)[ Chicago Holiday Rentals ](https://expedia.co.uk/Chicago-Holiday-Rentals.d178248.Travel-Guide-HolidayRentals)[ Chicago Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chicago.d178248.Car-Hire-Guide)[ Chicago Holidays ](https://expedia.co.uk/Chicago.d178248.Holidays-City-Breaks)[ Things to do in Chicago ](https://expedia.co.uk/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. 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