South Side Ski Holidays
Book a Ski Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top flight + Ski hotel deals in South Side
Hotel Riu Plaza Chicago
Reviewed on 17 Aug 2026
Kinzie Hotel
Reviewed on 17 Aug 2026
Level Chicago Fulton Market
Reviewed on 12 Aug 2026
Trump International Hotel & Tower Chicago
Reviewed on 16 Aug 2026
5* Ski holidays in South Side
Trump International Hotel & Tower Chicago
Reviewed on 16 Aug 2026
3 Night Ski holidays in South Side
4 Night Ski holidays in South Side
Hotel Riu Plaza Chicago
Reviewed on 17 Aug 2026
Level Chicago Fulton Market
Reviewed on 12 Aug 2026
Planning your South Side ski holiday
How can I book the best ski holiday to South Side in 2026/2027?
Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in South 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 South Side ski holidays?
Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book South 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 £934. Prices and availability are subject to change. Additional terms may apply.
Can I book last-minute ski holidays to South Side?
Use our handy last-minute deals page to look for ski holidays to South 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 South Side?
South 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 South Side?
All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in South 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 South Side?
Ski season in South 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 South 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 South 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 South Side that offer it.
Why should I book a ski holiday package in South 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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Ticket
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* 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.
