Southern Wisconsin Ski Vacations
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Top Ski vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥361,051
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) 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 Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
￥385,524
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) 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
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See all available trips from Osaka to Southern Wisconsin
View all trips5* Ski vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥361,051
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) 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
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips3 Night Ski vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥512,901
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kagoshima (KOJ) 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
Don't see what you're looking for?
See all available trips from Kagoshima to Southern Wisconsin
View all trips4 Night Ski vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥361,051
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) 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
Don't see what you're looking for?
See all available trips from Osaka to Southern Wisconsin
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
