Chicago Ski Holidays

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.

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 £559. Prices and availability are subject to change. Additional terms may apply.

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.

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.

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.

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.

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.

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.

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.