Title: Pet-friendly Vacations in Southern Wisconsin 2026 | Expedia.ca

![](https://images.trvl-media.com/place/2325/f29f5e3d-0eb0-45b8-94f1-06284f8af3d0.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# 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.

![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

CA $746

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,002 reviews)

It’s amazing historical property

Reviewed on Dec 15, 2025

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $1,902

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing

Reviewed on Dec 16, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,995

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Excellent stay. Loved everything about this hotel. Definitely coming back.

Reviewed on Dec 18, 2025

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $993

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $1,219

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Great location, clean room and friendly staff!

Reviewed on Dec 14, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southern Wisconsin

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Pet-friendly holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,543

per person

Mar 14 - Mar 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $1,902

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing

Reviewed on Dec 16, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,995

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Excellent stay. Loved everything about this hotel. Definitely coming back.

Reviewed on Dec 18, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southern Wisconsin

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Pet-friendly holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $724

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Excellent location to stay in the heart of the city.

Reviewed on Dec 17, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $971

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Excellent stay. Loved everything about this hotel. Definitely coming back.

Reviewed on Dec 18, 2025

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $1,150

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing

Reviewed on Dec 16, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southern Wisconsin

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Pet-friendly holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.

![Hyatt Place Chicago/ Schaumburg](https://images.trvl-media.com/lodging/1000000/90000/82300/82257/df623816_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Place Chicago/ Schaumburg

CA $469

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (1,000 reviews)

Everything was wonderful except those small square pillows, not sure who's idea that was

Reviewed on Dec 17, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,143

per person

Feb 17 - Feb 21

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Excellent stay. Loved everything about this hotel. Definitely coming back.

Reviewed on Dec 18, 2025

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $566

per person

Feb 17 - Feb 21

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southern Wisconsin

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Pet-friendly Hotels in Southern Wisconsin

![Polynesian Hotel & Suites Wisconsin Dells/Lake Delton](https://images.trvl-media.com/lodging/2000000/1220000/1216300/1216247/d2d04aa6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Polynesian Hotel & Suites Wisconsin Dells/Lake Delton

857 N Frontage Rd Wisconsin Dells WI

- 2 hours drive from University of Wisconsin-Madison

Book a stay at this family-friendly hotel in Wisconsin Dells. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...

5.8/10 (984 reviews)

They could work on cleaning better

Reviewed on Oct 26, 2025

[](https://expedia.ca/Wisconsin-Dells-Hotels-Polynesian-Water-Park-Resort.h1216247.Hotel-Information)

![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/fb616a0c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Madison Concourse Hotel and Governor's Club

1 W Dayton St Madison WI

- 5 min drive from University of Wisconsin-Madison

Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...

9.4/10 Exceptional! (3,375 reviews)

Room was very comfortable and well laid out. Perfect location.

Reviewed on Dec 15, 2025

[](https://expedia.ca/Madison-Hotels-The-Madison-Concourse-Hotel-And-Governors-Club.h28447.Hotel-Information)

![Drury Plaza Hotel Milwaukee Downtown](https://images.trvl-media.com/lodging/33000000/32510000/32501800/32501737/ac1d9528_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

- 3 hours drive from University of Wisconsin-Madison

Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...

9.6/10 Exceptional! (2,002 reviews)

Friendly staff, variety of breakfast food options.

Reviewed on Dec 14, 2025

[](https://expedia.ca/Milwaukee-Hotels-Drury-Plaza-Hotel-Milwaukee-Downtown.h32501737.Hotel-Information)

[See all 7,453 properties in Southern Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635975749457)

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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## More Vacations Ideas

[Flights to Southern Wisconsin

](https://expedia.ca/Cheap-Flights-To-Southern-Wisconsin.d553248635975749457.Travel-Guide-Flights)[

Southern Wisconsin Hotels

](https://expedia.ca/Southern-Wisconsin-Hotels.d553248635975749457.Travel-Guide-Hotels)[

Southern Wisconsin Vacation Rentals

](https://expedia.ca/Southern-Wisconsin-Vacation-Rentals.d553248635975749457.Travel-Guide-VacationRentals)[

Southern Wisconsin Car Rentals

](https://expedia.ca/Car-Rentals-In-Southern-Wisconsin.d553248635975749457.Car-Rental-Guide)[

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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.

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