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

West Side Adventure Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Adventure vacation packages in West Side

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

    Chicago Marriott Suites Deerfield + Flight

    Deerfield
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,003 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $723
    CA $621
    per traveller
    found 1 day ago
    Chicago Marriott Suites Deerfield
  • Jan 21 - Jan 24

    Lincolnshire Marriott Resort + Flight

    Half Day
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,001 reviews)
    "Very big property"
    Reviewed November 7, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $759
    CA $659
    per traveller
    found 1 day ago
    Lincolnshire Marriott Resort
  • Jan 21 - Jan 24

    Renaissance Chicago North Shore Hotel + Flight

    Northbrook
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,002 reviews)
    "One of the best beds I've ever slept in. Staff was amazing and friendly!"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $764
    CA $682
    per traveller
    found 1 day ago
    Renaissance Chicago North Shore Hotel
  • Dec 23 - Dec 28

    Motel 6 Palatine, IL - Chicago Northwest + Flight

    Palatine
    5 nights
    2.0 star property
    6.8/10 - (679 reviews)
    "Can be better"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $967
    CA $871
    per traveller
    found 1 day ago
    Motel 6 Palatine, IL - Chicago Northwest
  • Dec 25 - Dec 28

    Hyatt Regency Deerfield + Flight

    Deerfield
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,337 reviews)
    "Absolutely loved this hotel , the staff were very helpful!"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $710
    CA $641
    per traveller
    found 17 hours ago
    Hyatt Regency Deerfield

Discover the most popular places to visit in West Side

What to do in West Side

Top Adventure 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 $621. 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.