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.
Eaglewood Resort and Spa

Eaglewood Resort and Spa

￥238,776
per person
Nov 11 - Nov 16
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,367 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥342,158
per person
Nov 10 - Nov 17
found 8 hours ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
It’s a great location, great staff, comfy rooms. Great breakfast.

Reviewed on Oct 8, 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
￥311,696
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,352 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
￥530,538
per person
Nov 9 - Nov 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
￥239,056
per person
Dec 30 - Jan 2
found 2 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
Functional and I got what I needed

Reviewed on Oct 8, 2026

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4 Night Pet-friendly vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
￥300,418
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,309 reviews)
Well appointed rooms, kind staff, and very responsive

Reviewed on Oct 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥370,062
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
￥311,696
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,352 reviews)
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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.