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.
Level Chicago Fulton Market
Downtown Chicago
CA $1,069
per person
Dec 10 - Dec 15
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.
Reviewed on Sep 26, 2026
The Emily Hotel
Downtown Chicago
CA $1,238
per person
Dec 10 - Dec 15
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Front desk staff was great as was housekeeping staff. Rooms were nothing special. Shower and bathroom floor had moldy grout. Bed was absolutely awful. Felt like sleeping on golfballs. Bar staff was awful. Wanted a quick drink while waiting for an Uber. Told them to charge to room. Bartender went MIA so we asked, what we assumed was a manager to ring us, he said ‘yep’ then went on to make some drinks, ignoring us. For the $$$ you can find much better hotels.
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.
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,814
per person
Oct 28 - Oct 31
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 2026
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View all trips3 Night Pet-friendly holidays in Southern Wisconsin
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View all trips4 Night Pet-friendly holidays in Southern Wisconsin
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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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