Southern Wisconsin Beach Vacations

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Top Beach vacation packages in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
￥230,988
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥266,662
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Excellent staff, excellent location, great resort style breakfast buffet

Reviewed on Oct 17, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
￥251,392
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Close to every things, great location

Reviewed on Oct 16, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
￥234,910
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
￥249,120
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,934 reviews)
Don't see what you're looking for?
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4 Night Beach vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
￥230,988
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥266,662
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Excellent staff, excellent location, great resort style breakfast buffet

Reviewed on Oct 17, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
￥251,392
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Close to every things, great location

Reviewed on Oct 16, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.