Southern Wisconsin Mountain Vacations

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Top Mountain vacation packages in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥252,509
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious

Reviewed on Sep 23, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥321,148
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥252,717
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥279,525
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥751,216
per person
Nov 2 - Nov 7
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
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5* Mountain vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥321,148
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥498,178
per person
Nov 16 - Nov 20
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥751,216
per person
Nov 2 - Nov 7
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
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4 Night Mountain vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥252,509
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious

Reviewed on Sep 23, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥321,148
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥252,717
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Don't see what you're looking for?
See all available trips from Tokyo 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.