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. ![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 £337 per person 4 Apr - 6 Apr found 1 hour ago Return flight included Fayetteville (XNA) to Chicago (ORD) 9/10 Wonderful! (1,000 reviews) The room was clean and bright (although the view of a rooftop and skylight wasn’t great). The bed though! Comfortably firm — best nights sleep I’ve had in ages Reviewed on 8 Feb 2026 ![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 £740 per person 1 Apr - 5 Apr found 21 hours ago Return direct flight included London (LON) to Chicago (ORD) 8.8/10 Excellent! (1,128 reviews) The hotel is in excellent condition. Reviewed on 26 Jan 2026 ![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 £693 per person 16 Apr - 20 Apr found 6 hours ago Return flight included London (LHR) to Chicago (ORD) 7.8/10 Good! (1,192 reviews) The rooms were is great condition and the staff was really nice and helpful Reviewed on 8 Feb 2026 Don't see what you're looking for? See all available trips from Fayetteville to Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-09/2026-03-16/?FromAirport=XNA&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 £693 per person 16 Apr - 20 Apr found 6 hours ago Return flight included London (LHR) to Chicago (ORD) 7.8/10 Good! (1,192 reviews) The rooms were is great condition and the staff was really nice and helpful Reviewed on 8 Feb 2026 ![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 £740 per person 1 Apr - 5 Apr found 21 hours ago Return direct flight included London (LON) to Chicago (ORD) 8.8/10 Excellent! (1,128 reviews) The hotel is in excellent condition. Reviewed on 26 Jan 2026 ![La Quinta Inn & Suites by Wyndham Chicago Gurnee](https://images.trvl-media.com/lodging/1000000/60000/50200/50124/52a8ce1f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Quinta Inn & Suites by Wyndham Chicago Gurnee £698 per person 16 Apr - 20 Apr found 6 hours ago Return flight included London (LHR) to Chicago (ORD) 8/10 Very Good! (1,404 reviews) The hotel was clean, the staff was welcoming, and the atmosphere felt relaxing from the moment I arrived. My room was well-kept, with fresh linens. The bed was comfortable, and I appreciated the quiet environment, which made it easy to rest after a long day. Reviewed on 9 Feb 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/2026-03-09/2026-03-16/?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 £337\. 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/e60f0980_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 ... 9.8/10 Exceptional! (90 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! (1,104 reviews) Check in was fast and friendly. The room was outdated and smelled musty but it was clean and had all the basics. I would stay again Reviewed on 3 Feb 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/1000000/660000/658500/658492/96d51c6b_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 ... 8/10 Very Good! (1,000 reviews) Excellent Reviewed on 27 Jan 2026 [](https://expedia.co.uk/Algonquin-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Algonquin.h658492.Hotel-Information) [See all 5,624 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 > - 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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