Southern Wisconsin Mountain Vacations

Book a Mountain Hotel + Flight or Car together to unlock savings

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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)
Muy bien ubicado y en muy buen estado el Hotel !!

Reviewed on Sep 22, 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)
Room was clean and view was amazing

Reviewed on Sep 22, 2026

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)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
￥258,428
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,839 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)
Room was clean and view was amazing

Reviewed on Sep 22, 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
￥363,336
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Staff was excellent.

Reviewed on Sep 17, 2026

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)
Muy bien ubicado y en muy buen estado el Hotel !!

Reviewed on Sep 22, 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)
Room was clean and view was amazing

Reviewed on Sep 22, 2026

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.