Title: Pet-friendly Vacations in Northwest Side 2026 | Expedia.ca

![](https://images.trvl-media.com/place/829/2253d64b-0974-4770-85a9-32842b88f38f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Northwest Side Pet-friendly Vacations

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## Flight and Pet-friendly hotel deals in Northwest Side

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

![Eaglewood Resort and Spa](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/f931dcd0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eaglewood Resort and Spa

CA $557

per person

Mar 5 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

8.8/10 Excellent! (1,004 reviews)

Clean hotel, very friendly staff

Reviewed on Dec 9, 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 $873

per person

Jan 29 - Feb 1

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Amazing hotel, location, staff, and food!!

Reviewed on Dec 8, 2025

![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 $1,612

per person

Feb 23 - Feb 28

found 1 day ago

Roundtrip 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

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Chicago O'Hare Airport

O'Hare

CA $858

per person

Mar 5 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

8.2/10 Very Good! (2,158 reviews)

It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly.

Reviewed on Dec 6, 2025

![Sofitel Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/d0d24426_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sofitel Chicago Magnificent Mile

Downtown Chicago

CA $836

per person

Feb 23 - Feb 28

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (2,210 reviews)

I had an excellent stay at Sofitel. We were visiting for leisure. Prior to arriving, the concierge reached out to see if any accommodations were needed and the service was 10/10 from the moment we arrived to the time we checked out. Clean room, friendly staff, and in a convenient location for shopping. We also enjoyed dining during happy hour at Le Bar. I will definitely book Sofitel on my next visit to Chicago.

Reviewed on Dec 9, 2025

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Pet-friendly holidays in Northwest Side

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 $826

per person

Feb 19 - Feb 22

found 20 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Amazing hotel, location, staff, and food!!

Reviewed on Dec 8, 2025

![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 $1,612

per person

Feb 23 - Feb 28

found 1 day ago

Roundtrip 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 $1,183

per person

Feb 15 - Feb 18

found 6 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Excellent service throughout the hotel

Reviewed on Nov 29, 2025

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Pet-friendly holidays in Northwest Side

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

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Swissotel - Chicago

Downtown Chicago

CA $552

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,947 reviews)

The room is very clean, staff was great, the lobby bar and restaurant was very nice.

Reviewed on Dec 9, 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 $873

per person

Jan 29 - Feb 1

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Amazing hotel, location, staff, and food!!

Reviewed on Dec 8, 2025

![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 $580

per person

Jan 29 - Feb 1

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on Dec 4, 2025

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Pet-friendly holidays in Northwest Side

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

![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 $573

per person

Jan 29 - Feb 2

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Room was clean comfotable staff was super friendly. Complimentary breakfast was 5 star. Centrally located.Walking distance to many points of interest. Definitely would stay there again.

Reviewed on Dec 9, 2025

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Chicago O'Hare Airport

O'Hare

CA $858

per person

Mar 5 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

8.2/10 Very Good! (2,158 reviews)

It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly.

Reviewed on Dec 6, 2025

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Emily Hotel

Downtown Chicago

CA $812

per person

Jan 9 - Jan 13

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,264 reviews)

Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Pet-friendly Hotels in Northwest Side

![Quiet Area - Revamped Basement](https://images.trvl-media.com/lodging/95000000/94860000/94851600/94851534/659a4d05_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Quiet Area - Revamped Basement

 Chicago IL

- 18 min walk from Walt Disney House

Stay at this hotel in Chicago. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions United Center and Wrigley Field are located ...

9/10 Wonderful! (4 reviews)

We had a great stay here! The place was fantastic! Thanks!

Reviewed on Sep 11, 2025

[](https://expedia.ca/Chicago-Hotels-Quiet-Area-Revamped-Basement.h94851534.Hotel-Information)

![Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!](https://images.trvl-media.com/lodging/28000000/27140000/27138100/27138010/6dc56403_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

 Chicago IL

- 7 min drive from Walt Disney House

Book a stay at this family-friendly apartment in Chicago. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Portage Park and Copernicus Center ...

10/10 Exceptional! (112 reviews)

Jamie was an incredible host, she was very communicative and welcoming. The property is adorable and well appointed and in a great location!

Reviewed on Dec 3, 2025

[](https://expedia.ca/Chicago-Hotels-Cozy-Comfy-Clean-420-Compliant-FREE-Parking-QUIET-Neighborhood-A-GUEST-FAVORITE.h27138010.Hotel-Information)

![NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!](https://images.trvl-media.com/lodging/111000000/110770000/110760200/110760116/0de43d33_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!

 Chicago IL

- 6 min drive from Walt Disney House

Stay at this apartment in Chicago. Enjoy a garden, laundry facilities, and balconies. Popular attractions Wrigley Field and United Center are located ...

10/10 Exceptional! (11 reviews)

Everything was clean and well kept. Host was very accessible and friendly.

Reviewed on Oct 9, 2025

[](https://expedia.ca/Chicago-Hotels-ALL-NEW.h110760116.Hotel-Information)

[See all 5,131 properties in Northwest Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635976475367)

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 Northwest Side

](https://expedia.ca/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[

Northwest Side Hotels

](https://expedia.ca/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[

Northwest Side Vacation Rentals

](https://expedia.ca/Northwest-Side-Vacation-Rentals.d553248635976475367.Travel-Guide-VacationRentals)[

Northwest Side Car Rentals

](https://expedia.ca/Car-Rentals-In-Northwest-Side.d553248635976475367.Car-Rental-Guide)[

Northwest Side Vacations

](https://expedia.ca/Northwest-Side.d553248635976475367.Destination-Travel-Guides)

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