Title: Pet-friendly Vacations in Great Lakes 2026/2026 | Expedia.ca

![](https://images.trvl-media.com/place/4089/d972af62-8cc4-45b7-acc2-7d3d8f8eda5b.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Great Lakes Pet-friendly Vacations

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Photo by Leo Li

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## Flight and Pet-friendly hotel deals in Great Lakes

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

![Kimpton Gray Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13360000/13351500/13351499/14bf852a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kimpton Gray Hotel by IHG

Downtown Chicago

CA $482

per person

Feb 20 - Feb 22

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,003 reviews)

Spacious, beautifully decorated room. Beautiful architecture in the building. Great location close to lots of restaurants and shopping.

Reviewed on Nov 23, 2025

![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/2030b501_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Iron Horse Hotel

Fifth Ward

CA $988

per person

Feb 19 - Feb 22

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Milwaukee (MKE)

9.2/10 Wonderful! (1,008 reviews)

Walking in the place has a real warm feel. The folks that greeted me at the front desk were genuine, warm, and very kind. You can tell they love their work place. Customer Service was amazing!!! I had my dog and they had so many wonderful amenities for her from bowls, treats, a name board, a plush squeaky toy, and best of all a pink bandana! Spoiled rotten as was I. The food was good. The room was very clean and decorated beautifully. I loved the two days I stayed there and highly recommend it!

Reviewed on Dec 3, 2025

![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/eac2e31f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $823

per person

Feb 5 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Fredericton (YFC) to Chicago (ORD)

9.4/10 Exceptional! (1,003 reviews)

Perfect stay. Great location, lovely room with view of Marshall Fields State Street Christmas display. The people were just great.

Reviewed on Dec 3, 2025

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Chicago

Downtown Chicago

CA $854

per person

Feb 5 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Fredericton (YFC) to Chicago (ORD)

8.4/10 Very Good! (2,301 reviews)

We had a great stay and will be back again.

Reviewed on Dec 1, 2025

![Hilton Milwaukee](https://images.trvl-media.com/lodging/1000000/10000/6100/6090/cc399a7a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Milwaukee

Westown

CA $1,256

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

8.4/10 Very Good! (1,075 reviews)

Last minute booking and in a new part of town I usually stay. Very good hotel

Reviewed on Nov 29, 2025

Don't see what you're looking for?

See all available trips from Columbus to Great Lakes

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=null&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Pet-friendly holidays in Great Lakes

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

![Old Stone Inn Boutique Hotel](https://images.trvl-media.com/lodging/1000000/1000000/994200/994121/c13ec565_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Old Stone Inn Boutique Hotel

Fallsview

CA $486

per person

Feb 9 - Feb 12

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Toronto (YYZ)

7.8/10 Good! (1,455 reviews)

Everything was nice and welcoming

Reviewed on Dec 1, 2025

![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/2030b501_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Iron Horse Hotel

Fifth Ward

CA $988

per person

Feb 19 - Feb 22

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Milwaukee (MKE)

9.2/10 Wonderful! (1,008 reviews)

Walking in the place has a real warm feel. The folks that greeted me at the front desk were genuine, warm, and very kind. You can tell they love their work place. Customer Service was amazing!!! I had my dog and they had so many wonderful amenities for her from bowls, treats, a name board, a plush squeaky toy, and best of all a pink bandana! Spoiled rotten as was I. The food was good. The room was very clean and decorated beautifully. I loved the two days I stayed there and highly recommend it!

Reviewed on Dec 3, 2025

![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/eac2e31f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $823

per person

Feb 5 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Fredericton (YFC) to Chicago (ORD)

9.4/10 Exceptional! (1,003 reviews)

Perfect stay. Great location, lovely room with view of Marshall Fields State Street Christmas display. The people were just great.

Reviewed on Dec 3, 2025

Don't see what you're looking for?

See all available trips from Columbus to Great Lakes

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=null&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Pet-friendly holidays in Great Lakes

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

![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/eac2e31f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $596

per person

Feb 12 - Feb 16

found 14 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,003 reviews)

Perfect stay. Great location, lovely room with view of Marshall Fields State Street Christmas display. The people were just great.

Reviewed on Dec 3, 2025

![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 $632

per person

Feb 12 - Feb 16

found 14 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,159 reviews)

Modern vibes, a lot to see, eat and do at walking distance, spotless room and very comfy bed. Very friendly staff. Definitely would stay there again.

Reviewed on Nov 30, 2025

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Chicago

Downtown Chicago

CA $621

per person

Feb 12 - Feb 16

found 14 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very Good! (2,301 reviews)

We had a great stay and will be back again.

Reviewed on Dec 1, 2025

Don't see what you're looking for?

See all available trips from Columbus to Great Lakes

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=null&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Pet-friendly Hotels in Great Lakes

![Chelsea Hotel, Toronto](https://images.trvl-media.com/lodging/1000000/30000/28000/27994/c0edbb5d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Chelsea Hotel, Toronto

33 Gerrard St W Toronto ON

Book a stay at this family-friendly hotel in Toronto. Enjoy free WiFi, 2 indoor pools, and 2 restaurants. Our guests praise the pool and the restaurant in our ...

8.2/10 Very Good! (13,324 reviews)

Great location. Helpful staff

Reviewed on Nov 29, 2025

[](https://expedia.ca/Toronto-Hotels-Chelsea-Hotel.h27994.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

- 16 hours drive from Lake Superior

Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...

8.8/10 Excellent! (3,408 reviews)

Suite was roomy and spacious, the location wasn’t the best due to high traffic

Reviewed on Nov 29, 2025

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Great Canadian Casino Resort Toronto](https://images.trvl-media.com/lodging/95000000/94910000/94900100/94900038/4eef32ef_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Great Canadian Casino Resort Toronto

1133 Queens Plate Dr Toronto ON

Book a stay at this business-friendly hotel in Toronto. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the convenient parking ...

8.8/10 Excellent! (4,582 reviews)

Was quick check in. Busy place

Reviewed on Nov 29, 2025

[](https://expedia.ca/Toronto-Hotels-Great-Canadian-Casino-Resort-Toronto.h94900038.Hotel-Information)

[See all 79,245 properties in Great Lakes](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=6212870)

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 Great Lakes

](https://expedia.ca/Cheap-Flights-To-Great-Lakes.d6212870.Travel-Guide-Flights)[

Great Lakes Hotels

](https://expedia.ca/Great-Lakes-Hotels.d6212870.Travel-Guide-Hotels)[

Great Lakes Vacation Rentals

](https://expedia.ca/Great-Lakes-Vacation-Rentals.d6212870.Travel-Guide-VacationRentals)[

Great Lakes Car Rentals

](https://expedia.ca/Car-Rentals-In-Great-Lakes.d6212870.Car-Rental-Guide)[

Great Lakes Vacations

](https://expedia.ca/Great-Lakes.d6212870.Destination-Travel-Guides)[

Things to do in Great Lakes

](https://expedia.ca/Things-To-Do-In-Great-Lakes.d6212870.Travel-Guide-Activities)

\* 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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