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.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
₩593,308
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
₩704,555
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
₩1,190,004
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Great property

Reviewed on Oct 24, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
₩611,938
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
₩771,580
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.2/10 Wonderful! (1,163 reviews)
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5* Pet-friendly 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
₩1,190,004
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Great property

Reviewed on Oct 24, 2026

Don't see what you're looking for?
See all available trips from Des Moines to Southern Wisconsin
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3 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
₩611,938
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
₩704,555
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
₩1,190,004
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Great property

Reviewed on Oct 24, 2026

Don't see what you're looking for?
See all available trips from Des Moines 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.