A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.
Photo by throwingsofas
Open Photo by throwingsofas

West Side Ski Holidays

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Top Ski holiday packages in West Side

Price found within the past 48 hours. Click for updated prices.
  • 29 Dec - 3 Jan

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.4/10 - Very good (3,187 reviews)
    "Charged for an extra night that we didn’t stay and called and was told a reimbursement was completed. Five days later, the full charge for the night we didn’t stay posted in my account and with no reimbursement. When I called again, was told there was nothing they could do because the reimbursement was “released” and I would have to wait to talk to a manager when they arrived which would not be until the nighttime hours."
    Reviewed November 14, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,271
    €1,046
    per traveller
    found 6 hours ago
    Hotel Felix River North/Magnificent Mile
  • 29 Dec - 3 Jan

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.6/10 - Excellent (2,414 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,472
    €1,113
    per traveller
    found 6 hours ago
    Hotel Saint Clair- Magnificent Mile
  • 29 Dec - 3 Jan

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,585 reviews)
    "LOVE this hotel! Location is perfect and you can walk everywhere! Just wished they had a pool"
    Reviewed November 14, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,507
    €1,213
    per traveller
    found 6 hours ago
    Swissotel - Chicago
  • 29 Dec - 3 Jan

    Sports Illustrated Resorts Chicago + Flight

    Downtown Chicago
    5 nights
    3.5 star property
    9.0/10 - Wonderful (1,541 reviews)
    "Very clean and comfortable. Valet was helpful and kind"
    Reviewed November 13, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,367
    €1,116
    per traveller
    found 6 hours ago
    Sports Illustrated Resorts Chicago
  • 29 Dec - 3 Jan

    InterContinental Chicago Magnificent Mile by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (3,428 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,399
    €1,159
    per traveller
    found 6 hours ago
    InterContinental Chicago Magnificent Mile by IHG

Discover the most popular places to visit in West Side

What to do in West Side

Top Ski West Side 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.

Frequently Asked Questions

How much does a West Side holiday package cost?

Be ready to book, because a trip to West Side starts from an affordable €1,046. When you combine your flights, hotels and car rentals into a travel package, you'll score the best prices.

How do I get a cheap travel package to West Side?

It's easy. Just bundle. Flights, rental cars and hotels — combine whatever you need into a West Side holiday package to save a pile of cash. Score even better deals when you include extras such as activities or tours to your booking. But that's not the only good part. You have the flexibility to put together your holiday your own way. We offer more than 550 airlines and 1,000,000 hotels across the world, so that everyone has an opportunity to travel and live out those holiday fantasies.

What are the top hotels in West Side?

Grace Abbott Homes is one place that most travellers to West Side include in their itinerary. For a memorable stay here, take a look at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton.

How far in advance should I book my West Side holiday?

It can be tricky to know exactly when the best time is to book your West Side holiday. But generally the earlier you book, the cheaper the prices. Sometimes, you can lock in your flights and hotels nearly 12 months before departure. If you're thinking of a last-minute getaway, no need to worry! There are terrific deals popping up on Expedia every single day.

What does an Expedia West Side travel package include?

That depends on what you're after. If you're travelling alone, you might decide to bundle flights and hotels. Taking the whole crew to West Side? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility and freedom to tailor your travel package.

What should I know before booking a West Side travel package?

So many places to travel to, so many things to experience. With a travel package, you can cross more of them off your list. Bundle your flights, hotels and rental cars and get ready to save.

Can I choose my airline with a West Side Expedia holiday package?

Most definitely. Expedia has more than 550 airline partners to select from all over the world. With so much choice, finding the right carrier to get you to West Side shouldn't be hard.

If I'm not able to travel, can I cancel my West Side holiday package?

Don't worry if you're rethinking your West Side holiday package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.