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.
Arlo Chicago
Downtown Chicago
Price was CA $1,302, price is now CA $820 per person
CA $820
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,844 reviews)
This property was clean, lively and convenient to major attractions. The staff. Cleaning crew and front desk were exceptional
Reviewed on Sep. 7, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,903, price is now CA $1,148 per person
CA $1,148
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Location, cleanliness, and friendly staff
Reviewed on Sep. 7, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,352, price is now CA $827 per person
CA $827
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
The staff were very friendly and helpful, and the location in the city is excellent. My only complaint is that the walls are quite thin, so you can easily hear noise from the surrounding rooms.
Reviewed on Sep. 8, 2025
Level Chicago - River North
Downtown Chicago
Price was CA $1,759, price is now CA $1,142 per person
CA $1,142
per person
Oct 24 - Oct 29
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (679 reviews)
Rooms could be updated. Staff was under trained. Amenities very nice, used family room daily with our toddler. Pool deck very modern and new
Reviewed on Sep. 8, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,051, price is now CA $1,357 per person
CA $1,357
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
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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 $1,903, price is now CA $1,148 per person
CA $1,148
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Location, cleanliness, and friendly staff
Reviewed on Sep. 7, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,051, price is now CA $1,357 per person
CA $1,357
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,850, price is now CA $2,130 per person
CA $2,130
per person
Oct 12 - Oct 16
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
beautiful room and hotel great bar!
Reviewed on Sep. 7, 2025
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.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $854, price is now CA $550 per person
CA $550
per person
Nov 13 - Nov 16
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
The staff were very friendly and helpful, and the location in the city is excellent. My only complaint is that the walls are quite thin, so you can easily hear noise from the surrounding rooms.
Reviewed on Sep. 8, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,903, price is now CA $1,148 per person
CA $1,148
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Location, cleanliness, and friendly staff
Reviewed on Sep. 7, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,051, price is now CA $1,357 per person
CA $1,357
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
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 Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,352, price is now CA $827 per person
CA $827
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
The staff were very friendly and helpful, and the location in the city is excellent. My only complaint is that the walls are quite thin, so you can easily hear noise from the surrounding rooms.
Reviewed on Sep. 8, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,606, price is now CA $1,535 per person
CA $1,535
per person
Oct 29 - Nov 2
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Location, cleanliness, and friendly staff
Reviewed on Sep. 7, 2025
Don't see what you're looking for?
See all available trips from Columbus to Northwest Chicago
View all tripsMore vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
