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.

![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 $777

per person

Apr 16 - Apr 19

just found

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Banque Hotel

CA $956

per person

Apr 23 - Apr 28

found 1 hour ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (447 reviews)

Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $778

per person

Apr 16 - Apr 19

just found

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Amazing staff, very friendly, clean, comfortable, amazing breakfast.

Reviewed on Feb 1, 2026

![Central Loop Hotel](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/43ee742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Central Loop Hotel

Downtown Chicago

CA $920

per person

Apr 23 - Apr 28

found 1 hour ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

8.6/10 Excellent! (1,896 reviews)

I would not stay here again, unfortunately. The pictures make this hotel look a lot nicer than what we experienced. This hotel is on the older side, lobby was fine, but hallways smell like marijuana, and rooms are very small. Pay the extra money

Reviewed on Jan 30, 2026

![Hyatt Centric Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

CA $1,107

per person

Apr 23 - Apr 28

found 1 hour ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (1,034 reviews)

Yes, staff was great, hotel was great, the oat meal on the breakfast buffet was the best I have ever had. I crave it. Thank you for making our visit to Chicago wonderful!

Reviewed on Jan 21, 2026

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/2026-03-01/2026-03-08/?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.

![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 $1,032

per person

Apr 10 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

The room was boring thought it would be cleaner updated for the price best part was the view

Reviewed on Jan 24, 2026

![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 $1,521

per person

Mar 10 - Mar 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Chicago

Downtown Chicago

CA $1,526

per person

Mar 10 - Mar 15

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.8/10 Exceptional! (1,001 reviews)

Staff was wonderful.

Reviewed on Jan 25, 2026

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/2026-03-01/2026-03-08/?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 $777

per person

Apr 16 - Apr 19

just found

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $778

per person

Apr 16 - Apr 19

just found

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Amazing staff, very friendly, clean, comfortable, amazing breakfast.

Reviewed on Feb 1, 2026

![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 $1,060

per person

Mar 5 - Mar 8

found 4 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

The room was boring thought it would be cleaner updated for the price best part was the view

Reviewed on Jan 24, 2026

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/2026-03-01/2026-03-08/?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.

![Aloft Chicago Downtown River North](https://images.trvl-media.com/lodging/6000000/5470000/5461400/5461400/w4000h2662x0y0-8993d93f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Aloft Chicago Downtown River North

Downtown Chicago

CA $736

per person

Apr 9 - Apr 13

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (1,159 reviews)

Room and customer service was great!

Reviewed on Jan 20, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $820

per person

Apr 9 - Apr 13

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Amazing staff, very friendly, clean, comfortable, amazing breakfast.

Reviewed on Feb 1, 2026

![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 $895

per person

Apr 9 - Apr 13

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 2026

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/2026-03-01/2026-03-08/?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 (997 reviews)

Staff was very nice and the room was clean, furniture was very dated and well used. Beds were comfortable, bedding clean. Living room area was very dark with no windows. Shower/tub needs to be replaced. Refrigerator was adequate. Spacious, just needs a little updating.

Reviewed on Dec 31, 2025

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

![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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 ...

9.4/10 Exceptional! (1,927 reviews)

We felt like royalty!

Reviewed on Feb 1, 2026

[](https://expedia.ca/Milwaukee-Hotels-The-Pfister-Hotel.h19467.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! (3,478 reviews)

Everything was good.

Reviewed on Jan 30, 2026

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

[See all 7,403 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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[Flights to Southern Wisconsin

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

Southern Wisconsin Hotels

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