Southern Wisconsin Pet-friendly Vacations

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Top Pet-friendly 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
￥230,642
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Amables y todo cerca

Reviewed on Sep 30, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
￥270,104
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥343,518
per person
Nov 9 - Nov 13
just found
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
The parking wasn’t the best

Reviewed on Sep 29, 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
￥277,482
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,401 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
￥254,218
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,867 reviews)
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5* Pet-friendly vacations in Southern Wisconsin

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

Nobu Hotel Chicago

Downtown Chicago
￥356,482
per person
Nov 19 - Nov 23
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (922 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
￥422,594
per person
Nov 19 - Nov 23
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
￥526,716
per person
Nov 9 - Nov 13
just found
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
It is the greatest will be there again

Reviewed on Sep 29, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
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4 Night Pet-friendly 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
￥230,642
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Amables y todo cerca

Reviewed on Sep 30, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥342,510
per person
Nov 9 - Nov 13
found 20 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥343,518
per person
Nov 9 - Nov 13
just found
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
The parking wasn’t the best

Reviewed on Sep 29, 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.