Title: Pet-friendly Vacations in Central Chicago 2026 | Expedia.ca

![](https://images.trvl-media.com/place/829/bd91735e-0c7e-4d0c-8152-a9d6fd38ff30.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Central Chicago Pet-friendly Vacations

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Photo by Phil Ostroff

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## Flight and Pet-friendly hotel deals in Central Chicago

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

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $762

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,229 reviews)

Great experience with no problems

Reviewed on Jan 27, 2026

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $1,000

per person

Mar 13 - Mar 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (766 reviews)

Great stay. Would come again.

Reviewed on Jan 19, 2026

![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 $980

per person

Mar 13 - Mar 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Clean room and amenities

Reviewed on Jan 8, 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 $1,116

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip non-stop 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

![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Virgin Hotels Chicago

Downtown Chicago

CA $1,088

per person

Mar 13 - Mar 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,404 reviews)

Staff was super friendly and rooms were clean. Definitely will come back

Reviewed on Jan 20, 2026

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Pet-friendly holidays in Central Chicago

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 $1,116

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip non-stop 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

![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 3 hours 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 3 hours 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 Central Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Pet-friendly holidays in Central Chicago

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

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $762

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,229 reviews)

Great experience with no problems

Reviewed on Jan 27, 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 $850

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Room was clean, comfortable and quiet.

Reviewed on Jan 30, 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 $1,116

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip non-stop 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 Central Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Pet-friendly holidays in Central Chicago

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 $813

per person

Mar 2 - Mar 6

found 15 hours ago

Roundtrip 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

![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 $997

per person

Mar 2 - Mar 6

found 15 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Clean room and amenities

Reviewed on Jan 8, 2026

![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $845

per person

Mar 2 - Mar 6

found 15 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9.2/10 Wonderful! (317 reviews)

Service was amazing and the location was perfect. Would definitely stay here again.

Reviewed on Jan 28, 2026

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Pet-friendly Hotels in Central Chicago

![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St Chicago IL

- 3 min walk from Michigan Avenue

Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...

8.6/10 Excellent! (2,267 reviews)

2nd time at hotel and will come again.

Reviewed on Jan 28, 2026

[](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago

720 S Michigan Ave Chicago IL

- 26 min walk from Michigan Avenue

Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...

8.4/10 Very Good! (2,584 reviews)

My stay was truly amazing. Thank you and appreciate the hotel hospitality

Reviewed on Jan 25, 2026

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.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

- 11 min walk from Michigan Avenue

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! (3,761 reviews)

Excellent

Reviewed on Jan 26, 2026

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

[See all 1,515 properties in Central Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635976475413)

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 Central Chicago

](https://expedia.ca/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights)[

Central Chicago Hotels

](https://expedia.ca/Central-Chicago-Hotels.d553248635976475413.Travel-Guide-Hotels)[

Central Chicago Vacation Rentals

](https://expedia.ca/Central-Chicago-Vacation-Rentals.d553248635976475413.Travel-Guide-VacationRentals)[

Central Chicago Car Rentals

](https://expedia.ca/Car-Rentals-In-Central-Chicago.d553248635976475413.Car-Rental-Guide)[

Central Chicago Vacations

](https://expedia.ca/Central-Chicago.d553248635976475413.Destination-Travel-Guides)[

Things to do in Central Chicago

](https://expedia.ca/Things-To-Do-In-Central-Chicago.d553248635976475413.Travel-Guide-Activities)

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