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.
Four Seasons Hotel Chicago
Downtown Chicago
Price was CA $2,517, price is now CA $1,767 per person
CA $1,767
per person
Oct 13 - Oct 16
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Late on room service. Forgot items requested, making room service even later.
Tv was not plugged in correctly and wasted my time. If i pay this much for a room for 2 nights I really expect these simple things to work the first time and me not have to waste my time trying to figure out why the tv isnt working.
Idk i think some of the staff is a little confused or lazy im not sure. Beautiful hotel and beautiful room with a great view.
Also the wings from room service could be SOO muchh better. Thanks for taking all my money tho!
Reviewed on Aug 4, 2026
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View all trips5* Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was CA $2,517, price is now CA $1,767 per person
CA $1,767
per person
Oct 13 - Oct 16
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Late on room service. Forgot items requested, making room service even later.
Tv was not plugged in correctly and wasted my time. If i pay this much for a room for 2 nights I really expect these simple things to work the first time and me not have to waste my time trying to figure out why the tv isnt working.
Idk i think some of the staff is a little confused or lazy im not sure. Beautiful hotel and beautiful room with a great view.
Also the wings from room service could be SOO muchh better. Thanks for taking all my money tho!
Reviewed on Aug 4, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,634, price is now CA $2,028 per person
CA $2,028
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Excellent hotel in the heart of Chicago on the river. The hotel staff are fabulous! We stayed on the club level and liked it very much. The club room has beverages and food items all day. The view over and down the river is spectacular. Highly recommend the hotel.
Reviewed on Aug 3, 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.
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View all trips4 Night Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,441, price is now CA $950 per person
CA $950
per person
Oct 26 - Oct 30
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (144 reviews)
This hotel was so unique. The decorations are so cool! Overall, the hotel was clean and well maintained. The restaurant/bar is excellent!
Reviewed on Aug 4, 2026
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See all available trips from Columbus to Northwest Chicago
View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Chicago By Night River and Lake Cruise
CA $70
per adult
92% of travellers recommend
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