Southern Wisconsin Mountain Vacations
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Flight and Mountain hotel deals in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,436
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is an elegant and high class facility with warm service and hospitality stuff
Centrally located on North River north bank.
The room is big and spacious overlooking the river.
We loved our stay.
The concierge gave us a great tips and services
Recommend by all means.
Reviewed on Oct 2, 2026
The Peninsula Chicago
Downtown Chicago
CA $2,564
per person
Dec 13 - Dec 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class
Reviewed on Oct 1, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,676
per person
Dec 13 - Dec 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 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
Level Chicago – Old Town
Downtown Chicago
CA $1,118
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
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View all trips5* Mountain holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,436
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is an elegant and high class facility with warm service and hospitality stuff
Centrally located on North River north bank.
The room is big and spacious overlooking the river.
We loved our stay.
The concierge gave us a great tips and services
Recommend by all means.
Reviewed on Oct 2, 2026
The Peninsula Chicago
Downtown Chicago
CA $2,564
per person
Dec 13 - Dec 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class
Reviewed on Oct 1, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,676
per person
Dec 13 - Dec 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 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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See all available trips from Columbus to Southern Wisconsin
View all trips3 Night Mountain holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,436
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is an elegant and high class facility with warm service and hospitality stuff
Centrally located on North River north bank.
The room is big and spacious overlooking the river.
We loved our stay.
The concierge gave us a great tips and services
Recommend by all means.
Reviewed on Oct 2, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,118
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips4 Night Mountain holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
CA $1,306
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
CA $1,639
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
I stayed in a room at the back, every morning at 5:30 am trucks and dumpsters were moved, noise so loud it woke me up.
Was charged an amenity fee and there were really mo amenities. Breakfast sucked both days in first floor restaurant. Won't stay again.
Reviewed on Oct 1, 2026
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See all available trips from Columbus to Southern Wisconsin
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