Northwest Chicago Mountain Vacations
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Flight and Mountain hotel deals in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
CA $1,081
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Property was clean. Staff was so lovely. Asked if special occasion and sent some drinks up. Overall great location and convenient. On the downside - noisy location also and difficult to get rooftop seating. It is not a bar rooftop. Flew into O’Hare and took subway and from there walked to hotel w one carry on suitcase.
Reviewed on Sep 23, 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
CA $2,401
per person
Nov 14 - Nov 18
found 1 hour ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
The room was great and the roof top bar was a great time.
Reviewed on Sep 21, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,273
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 2026
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View all trips5* Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,273
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 2026
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View all trips3 Night Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
CA $1,216
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,077 reviews)
Outstanding room. I highly recommend. Be sure to check out the 6th floor and all the amenities!
Reviewed on Sep 23, 2026
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View all trips4 Night Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
CA $1,270
per person
Nov 14 - Nov 18
found 1 hour ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Great stay in an elegant mostly residential building. Smooth check in, but had to fill out a few forms. Very nice staff. Young building with lots of dogs yay!
Reviewed on Sep 24, 2026
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View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
