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

West Side Mountain Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Mountain vacation packages in West Side

Price found within the past 48 hours. Click for updated prices.
  • Jan 21 - Jan 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,881 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,134
    CA $822
    per traveller
    found 11 hours ago
    Sheraton Grand Chicago Riverwalk
  • Jan 8 - Jan 11

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,008 reviews)
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $2,118
    CA $1,439
    per traveller
    found 21 hours ago
    The Peninsula Chicago
  • Jan 1 - Jan 7

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (604 reviews)
    "Weird space w the way the bed is no access off the side and the counter was stained badly. There was a 28$ additional amenity fee that they slapped on upon check in. The pool is closed and didn’t use the weight room it was a one night stay. over priced but could be ok for a long stay w the kitchen"
    Reviewed November 6, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • Nonstop
    CA $1,693
    CA $1,262
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Dec 28 - Jan 1

    The Blackstone, Autograph Collection + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.0/10 - Wonderful (1,003 reviews)
    "Nice property but a little worn.mattresses were not that comfortable .Some staff were great, others not so much."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,195
    CA $897
    per traveller
    found 1 day ago
    The Blackstone, Autograph Collection
  • Dec 28 - Jan 1

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (195 reviews)
    "Hotel was very nice and clean. The location was excellent."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,144
    CA $864
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection

Discover the most popular places to visit in West Side

What to do in West Side

Top Mountain 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 vacation package cost?

Be ready to book, because a trip to West Side starts from an affordable CA $822. 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 vacation 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 vacation 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 vacation fantasies.

What are the top hotels in West Side?

Grace Abbott Homes is one place that most travelers 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 vacation?

It can be tricky to know exactly when the best time is to book your West Side vacation. 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 traveling 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 vacation 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 vacation package?

Don't worry if you're rethinking your West Side vacation 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.