Title: Southern Wisconsin Ski Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/2325/f29f5e3d-0eb0-45b8-94f1-06284f8af3d0.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southern Wisconsin Ski Holidays ## Book a Ski Hotel + Flight or Car together to unlock savings Photo by Evae - ## 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 Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago £1,063 per person 20 May - 27 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 8.2/10 Very Good! (2,573 reviews) the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back. Reviewed on 4 Mar 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 Save 100% on your flight £1,301 per person 20 May - 27 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Plenty of stores and restaurants around. Great location downtown. Short walk to the river. Very clean and new. Reviewed on 9 Mar 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £1,342 per person 20 May - 27 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,310 reviews) Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again. Reviewed on 7 Mar 2026 ![Sports Illustrated Resorts Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/bc30a848_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sports Illustrated Resorts Chicago Downtown Chicago £1,237 per person 20 May - 27 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,407 reviews) Check in was quick and easy, room was clean and spacious Reviewed on 9 Mar 2026 ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Magnificent Mile Downtown Chicago £1,231 per person 20 May - 27 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (3,285 reviews) Great stay. Staff was slightly inattentive at times with requests for things to room. Reviewed on 9 Mar 2026 Don't see what you're looking for? See all available trips from London to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/29a217ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago £1,403 per person 5 May - 8 May found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,001 reviews) Great location, service, and gym Reviewed on 24 Jan 2026 ![Nobu Hotel Chicago](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/ccd16d9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Nobu Hotel Chicago Downtown Chicago £2,311 per person 20 May - 27 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (795 reviews) This was an amazing stay. The staff was incredibly helpful and welcoming. In a gray lo Reviewed on 9 Mar 2026 Don't see what you're looking for? See all available trips from London to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in Southern Wisconsin 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 £743 per person 27 Apr - 30 Apr found 1 day ago Return direct flight included Glasgow (GLA) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Plenty of stores and restaurants around. Great location downtown. Short walk to the river. Very clean and new. Reviewed on 9 Mar 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £891 per person 27 Apr - 30 Apr found 1 day ago Return direct flight included Glasgow (GLA) to Chicago (ORD) 9.4/10 Exceptional! (1,137 reviews) Front desk staff are gems! They knew my name after 1 interaction and were very attentive. The room amenities were very nice-- espresso, bottled water, chocolates, steamer, toiletries. Reviewed on 1 Mar 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £919 per person 27 Apr - 30 Apr found 1 day ago Return direct flight included Glasgow (GLA) to Chicago (ORD) 9.2/10 Wonderful! (1,310 reviews) Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again. Reviewed on 7 Mar 2026 Don't see what you're looking for? See all available trips from Glasgow to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=GLA&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your Southern Wisconsin ski holiday #### How can I book the best ski holiday to Southern Wisconsin in 2026/2027? Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Southern Wisconsin. 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 Southern Wisconsin ski holidays? Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Southern Wisconsin 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 £743\. Prices and availability are subject to change. Additional terms may apply. #### Can I book last-minute ski holidays to Southern Wisconsin? Use our handy last-minute deals page to look for ski holidays to Southern Wisconsin 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 Southern Wisconsin? Southern Wisconsin 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 Southern Wisconsin? All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Southern Wisconsin. 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 Southern Wisconsin? Ski season in Southern Wisconsin 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 Southern Wisconsin 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 Southern Wisconsin 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 Southern Wisconsin that offer it. #### Why should I book a ski holiday package in Southern Wisconsin 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 Southern Wisconsin ](https://expedia.co.uk/Cheap-Flights-To-Southern-Wisconsin.d553248635975749457.Travel-Guide-Flights)[ Southern Wisconsin Hotels ](https://expedia.co.uk/Southern-Wisconsin-Hotels.d553248635975749457.Travel-Guide-Hotels)[ Southern Wisconsin Holiday Rentals ](https://expedia.co.uk/Southern-Wisconsin-Holiday-Rentals.d553248635975749457.Travel-Guide-HolidayRentals)[ Southern Wisconsin Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southern-Wisconsin.d553248635975749457.Car-Hire-Guide)[ Southern Wisconsin Holidays ](https://expedia.co.uk/Southern-Wisconsin.d553248635975749457.Holidays-City-Breaks) \* 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