Winter stays that sparkle

From ski trips to shopping breaks, embrace sweater season with an unforgettable winter stay.

Wrap up for a winter city breakWrap up for a winter city break

There's something magical about winter in a city. Check out our top picks and activities and start planning a trip to remember.

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Winter in Chicago

Winter in the Windy City offers plenty of cold-weather activities. Lace up your ice skates for the large rink in Millennium Park or try the track at Maggie Daley Park. If sledding is more your thing, there’s a 33-foot slope at Soldier Field.

A trip to Chicago isn’t complete without taking in the great views of the city at Lake Michigan, and it’s even more magical when the lake is frozen.

Complete your trip with a visit to the Chriskindlmarket Christmas market or do some holiday shopping on Magnificent Mile.

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Where will you be this winter?

Whether you’re chasing the snow or just looking to relax, we’ve got the stay for you, from cozy resorts to spa and golf trips.

Hit the slopes

With hotels and resorts in many of the world’s top skiing destinations, from Whistler, Canada, to Niseko Village, Japan, a ski trip with Hilton is a peak choice. Many of our hotels offer slope-side access, allowing you to completely immerse yourself in the snowy experience. And with amenities like spas, pools, and great dining, we’ve got you covered for après-ski.

Discover Ski Resorts and Hotels

It's snow time

Discover the wonders of winter and make the most of snowball season with our insider knowledge.

Winter, your wayWinter, your way

Personalize your stay with what matters most to you, from being close to family to traveling with your pets.

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The perfect place for PTO (Pet Time Off)

Furry friends are family, too. So bring them along on your winter pet-away. We welcome four-legged guests at over 5,000 hotels nationwide with open arms and belly rubs.

*Fees apply and vary by hotel.

Explore Pet-Friendly HotelsExplore our pet-friendly hotels
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Ready for some winter magic? Book your next stay today. Let's Go

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Waldorf Astoria

Offers unforgettable experiences at iconic destinations around the world.