Southern Wisconsin Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,607
per person
Nov 20 - Nov 23
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Great hotel the staff was very helpful.
Very clean just overall a very impressive hotel and staff. Will definitely stay there again.
Reviewed on Sep 28, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,286
per person
Nov 15 - Nov 19
found 6 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
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View all trips5* Pet-friendly holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,607
per person
Nov 20 - Nov 23
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Great hotel the staff was very helpful.
Very clean just overall a very impressive hotel and staff. Will definitely stay there again.
Reviewed on Sep 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips3 Night Pet-friendly holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,607
per person
Nov 20 - Nov 23
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Great hotel the staff was very helpful.
Very clean just overall a very impressive hotel and staff. Will definitely stay there again.
Reviewed on Sep 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips4 Night Pet-friendly holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $2,132
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Great hotel the staff was very helpful.
Very clean just overall a very impressive hotel and staff. Will definitely stay there again.
Reviewed on Sep 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all tripsPet-friendly Hotels in Southern Wisconsin
Grand Geneva Resort & Spa
7036 Grand Geneva Wy Lake Geneva WI
- 2 hours drive from University of Wisconsin-Madison
Book a stay at this spa resort in Lake Geneva. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
- 3 hours drive from University of Wisconsin-Madison
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
- 3 hours drive from University of Wisconsin-Madison
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.
