A city skyline at dusk with illuminated buildings reflecting on the water.

Photo by Phil Ostroff

Central Chicago Ski Holidays

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  • Top Ski holiday packages in Central Chicago

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    Discover the most popular places to visit in Central Chicago

    A modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

    McCormick Place

    Rating: 8.8/10 (9,822 reviews)

    Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

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    A Ferris wheel and a carousel at a fairground.

    Navy Pier

    Rating: 9.0/10 (24,140 reviews)

    A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

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    A large stadium surrounded by a cityscape with modern buildings.

    Photo by © City of Chicago

    Soldier Field

    Rating: 8.8/10 (7,063 reviews)

    Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

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    A large metallic sphere sculpture in a public square surrounded by tall buildings.

    Photo by TM

    Millennium Park

    Rating: 9.4/10 (30,446 reviews)

    A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

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    A cityscape at night with illuminated buildings, a river, and a bridge.

    Photo by TM

    Chicago Riverwalk

    Rating: 9.6/10 (13,574 reviews)

    Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

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    A city street at night with illuminated buildings, a snow-covered sidewalk, and light trails from moving vehicles.

    Michigan Avenue

    Rating: 9.4/10 (15,813 reviews)

    You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

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    A modern cityscape with a distinctive metallic sculpture in the foreground and a variety of skyscrapers in the background.

    Grant Park

    Rating: 9.2/10 (12,844 reviews)

    Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

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    A city skyline with tall skyscrapers, a river, and a bridge.

    Willis Tower

    Rating: 9.0/10 (9,893 reviews)

    Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

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    What to do in Central Chicago

    360 CHICAGO Observation Deck  (Hancock Center)

    360 CHICAGO Observation Deck

    £18

    per adult

    86% of travellers recommend

    Skydeck Chicago at Willis Tower

    Skydeck Chicago at Willis Tower

    £32

    per adult

    84% of travellers recommend

    Wendella's 90-min Chicago River Architecture Tour

    Wendella's 90-min Chicago River Architecture Tour

    £30

    per adult

    94% of travellers recommend

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    Top Ski Central Chicago Hotels

    JW Marriott Chicago

    A grand lobby with a large Christmas tree, marble floors, and a staircase.
    • Address: 151 West Adams Street, Chicago, IL, 60603, US
    • Location: Theatre District, 0.3 mi from Central Chicago
    • Star rating: 4.5/5
    • Guest rating: 9.2/10 (Wonderful, 1000 reviews)
    • Price: £194, includes taxes & fees, 26 Nov - 27 Nov, for Top Ski Central Chicago Hotels

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    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 £5,340. 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.

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