A curved pathway with a metal fence, flowering trees, and a street lamp.

Northwest Side Mountain Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $4,200 when you book a flight and hotel together*
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Top Mountain vacation packages in Northwest 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 (1,882 reviews)
    "First time ever in Chicago and it was fabulous. The hotel was beautiful. Staff was friendly. We paid for the view and it was phenomenal. Definitely recommend."
    Reviewed November 12, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,111
    CA $797
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Dec 29 - Jan 3

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (609 reviews)
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • Nonstop
    CA $1,806
    CA $1,261
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Jan 21 - Jan 24

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,944
    CA $1,379
    per traveller
    found 1 day ago
    The Peninsula Chicago
  • Dec 29 - Jan 3

    Park Hyatt Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,000 reviews)
    "This place was amazing and the hotel staff was extremely helpful"
    Reviewed November 10, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • Nonstop
    CA $3,257
    CA $2,340
    per traveller
    found 1 day ago
    Park Hyatt Chicago
  • Dec 27 - Dec 31

    Level Chicago - River North + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,173 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YKF - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,400
    CA $1,007
    per traveller
    found 1 day ago
    Level Chicago - River North

Discover the most popular places to visit in Northwest Side

Frequently Asked Questions

How much does a Northwest Side vacation package cost?

Explore the best of Northwest Side from just CA $797. Choose from a great selection of rental cars, hotels and flights to suit every budget. Land even better deals when you add a few experiences or tours to your package.

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

Book everything all in one place with our Northwest Side vacation packages. We have deals on flights, hotels, tours and more that'll keep your pocketbook happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 hotel options globally to choose from, you'll have the flexibility to mix and match as you like.

How far in advance should I book my Northwest Side vacation?

Savvy travelers often reserve their seats early. You can generally look up international airfares on Expedia up to a year before your intended flight. If you're late to book, don't despair. Low prices occasionally become available just weeks prior to departure.

What does an Expedia Northwest Side travel package include?

Hotels, rental cars and flights, or any combination of the three — you decide! Whether you're headed to Northwest Side on a family road trip or traveling solo, there's a package to fit every budget and style. Once you've made your booking, why not add on some activities?

Can I choose my airline with a Northwest Side Expedia vacation package?

Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our vacation packages give you the flexibility to pick from available flights, hotels and activities that suit you.

If I'm not able to travel, can I cancel my Northwest Side vacation package?

Because we understand life is full of surprises, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.