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.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,339
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Front desk staff unfriendly and somewhat rude. We put sign to clean room and left in the morning and returned around 3:00 PM and room was still not clean. I called service desk and he apologized and said they’re just too busy and will come by 5:30PM. When they did show up we had to leave the room and wait for them to finish. Unacceptable!!!!!
Reviewed on Sep 11, 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 $1,383
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The view from the room was amazing. The staff was friendly and very helpful. Would highly recommend. Location was excellent.
Reviewed on Sep 11, 2026
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View all trips3 Night Pet-friendly holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,146
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
The hotel was amazing and it had the best view of Chicago skyline and lake views. The rooftop restaurant was beautiful and navy pier at your front door. I’m looking forward to returning soon.
Reviewed on Sep 11, 2026
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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 $1,544
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The view from the room was amazing. The staff was friendly and very helpful. Would highly recommend. Location was excellent.
Reviewed on Sep 11, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,339
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Front desk staff unfriendly and somewhat rude. We put sign to clean room and left in the morning and returned around 3:00 PM and room was still not clean. I called service desk and he apologized and said they’re just too busy and will come by 5:30PM. When they did show up we had to leave the room and wait for them to finish. Unacceptable!!!!!
Reviewed on Sep 11, 2026
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See all available trips from Columbus to Southern Wisconsin
View all tripsPet-friendly Hotels in Southern Wisconsin
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
- 7 min drive from American Family Field
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 ...
Grand Geneva Resort & Spa
7036 Grand Geneva Wy Lake Geneva WI
- 1 hour drive from American Family Field
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 ...
8.8/10 Excellent! (1,000 reviews)
"Nice staff everywhere. Bar, restaurants, front desk...one disturbing thing though...Asked 3-4 people at front desk if I could get the Milwaukee Brewer game on TV....they had no clue. I found a "Milwaukee" channel guide on the TV, which turned out was impossible to use....also no one knew about that. ..."
Reviewed on Sep 9, 2026
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
- 6 min drive from American Family Field
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 ...
8.6/10 Excellent! (1,446 reviews)
"I don't like any place where you have to pay for the parking."
Reviewed on Sep 11, 2026
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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