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
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,001, price is now CA $2,200 per person
CA $2,200
per person
Dec 16 - Dec 21
found 5 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Very good service
Reviewed on Nov 9, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Chicago
View all trips5* Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,001, price is now CA $2,200 per person
CA $2,200
per person
Dec 16 - Dec 21
found 5 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Very good service
Reviewed on Nov 9, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Chicago
View all trips3 Night Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Chicago
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 $1,880, price is now CA $1,336 per person
CA $1,336
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
I’ve stayed at Talbott before and enjoyed it, but this time was pretty disappointing! Towel and amenity services were awful and the shower was very poor pressure.
Reviewed on Nov 8, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,388, price is now CA $1,037 per person
CA $1,037
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
Location is great. Room is small.
Reviewed on Nov 8, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Chicago
View all tripsThings to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% 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.
