Title: Central Chicago Ski Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/829/bd91735e-0c7e-4d0c-8152-a9d6fd38ff30.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Central Chicago Ski Holidays ## Book a Ski Hotel + Flight or Car together to unlock savings Photo by Phil Ostroff - ## 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 Central Chicago 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 £776 per person 23 Mar - 28 Mar just found Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Hotel Riu was a very pleasant stay and I most definitely will be staying again. Room was spotless and housekeeping did an amazing job and left all my belongings exactly where i kept them. Staff was super professional, my wife and I felt welcomed with their behavior and work ethic. Delicious all-inclusive breakfast that tasted homemade, unlike other hotels that serve frozen or reheated food. Smooth check out with no hidden fees! Definitely a hotel that deserves a chance. Reviewed on 15 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 Save 100% on your flight £1,230 per person 23 Mar - 28 Mar just found Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return. Reviewed on 5 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 £1,134 per person 23 Mar - 28 Mar just found Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing Reviewed on 13 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 £881 per person 23 Mar - 28 Mar just found Return direct flight included London (LGW) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Nice newer hotel with lots of options. Rooms are a bit industrial but fine, nothing super luxurious but adequate. Reviewed on 16 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 £876 per person 23 Mar - 28 Mar just found Return direct flight included London (LGW) to Chicago (ORD) 9/10 Wonderful! (380 reviews) I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay. Reviewed on 12 Jan 2026 Don't see what you're looking for? See all available trips from London to Central Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-16/2026-02-23/?FromAirport=LGW&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Central Chicago Price found within the past 48 hours. Click for updated prices. ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago £1,130 per person 23 Mar - 28 Mar just found Return direct flight included London (LGW) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Yes didn’t know you get free breakfast Reviewed on 4 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 Save 100% on your flight £1,230 per person 23 Mar - 28 Mar just found Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return. Reviewed on 5 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 £1,134 per person 23 Mar - 28 Mar just found Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing Reviewed on 13 Jan 2026 Don't see what you're looking for? See all available trips from London to Central Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-16/2026-02-23/?FromAirport=LGW&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in Central Chicago 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 £498 per person 25 Feb - 28 Feb found 1 day ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Hotel Riu was a very pleasant stay and I most definitely will be staying again. Room was spotless and housekeeping did an amazing job and left all my belongings exactly where i kept them. Staff was super professional, my wife and I felt welcomed with their behavior and work ethic. Delicious all-inclusive breakfast that tasted homemade, unlike other hotels that serve frozen or reheated food. Smooth check out with no hidden fees! Definitely a hotel that deserves a chance. Reviewed on 15 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 £738 per person 25 Feb - 28 Feb found 1 day ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing Reviewed on 13 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 £606 per person 25 Feb - 28 Feb found 1 day ago Return direct flight included London (LGW) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Nice newer hotel with lots of options. Rooms are a bit industrial but fine, nothing super luxurious but adequate. Reviewed on 16 Jan 2026 Don't see what you're looking for? See all available trips from London to Central Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-16/2026-02-23/?FromAirport=LGW&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Central Chicago 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 £704 per person 7 Apr - 11 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Hotel Riu was a very pleasant stay and I most definitely will be staying again. Room was spotless and housekeeping did an amazing job and left all my belongings exactly where i kept them. Staff was super professional, my wife and I felt welcomed with their behavior and work ethic. Delicious all-inclusive breakfast that tasted homemade, unlike other hotels that serve frozen or reheated food. Smooth check out with no hidden fees! Definitely a hotel that deserves a chance. Reviewed on 15 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 £777 per person 7 Apr - 11 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay. Reviewed on 12 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 £1,056 per person 7 Apr - 11 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing Reviewed on 13 Jan 2026 Don't see what you're looking for? See all available trips from London to Central Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-16/2026-02-23/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your Central Chicago ski holiday #### How can I book the best ski holiday to Central Chicago in 2026/2027? Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Central 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 Central Chicago ski holidays? Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Central 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 £498\. Prices and availability are subject to change. Additional terms may apply. #### Can I book last-minute ski holidays to Central Chicago? Use our handy last-minute deals page to look for ski holidays to Central 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 Central Chicago? Central 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 Central Chicago? All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Central 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 Central Chicago? Ski season in Central 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 Central 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 Central 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 Central Chicago that offer it. #### Why should I book a ski holiday package in Central 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. ## 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