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

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

![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Orrington / Evanston

Downtown Evanston

CA $913

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

7.6/10 Good! (1,002 reviews)

Clean room, good service and great area.

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 $1,902

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

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $1,060

per person

Mar 14 - Mar 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (347 reviews)

While the staff was very nice and accommodating, the bathroom lock in my room was broken which resulted in me getting locked inside on my first night. It took maintenance/staff 45 minutes to get me out, which resulted in me being late for dinner reservations. I would like to say--Langston is the one who finally set me free and he was great and incredibly apologetic.

Reviewed on Dec 15, 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 $1,259

per person

Mar 1 - Mar 4

found 2 days ago

Roundtrip non-stop flight included

Montreal (YMQ) 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

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/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

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

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 $1,259

per person

Mar 1 - Mar 4

found 2 days ago

Roundtrip non-stop flight included

Montreal (YMQ) 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 Central Chicago

[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 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 $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 $1,201

per person

Mar 1 - Mar 4

found 2 days ago

Roundtrip non-stop flight included

Montreal (YMQ) 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

![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 $1,259

per person

Mar 1 - Mar 4

found 2 days ago

Roundtrip non-stop flight included

Montreal (YMQ) 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

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/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Pet-friendly holidays in Central Chicago

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 $1,317

per person

Mar 14 - Mar 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

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

Reviewed on Dec 18, 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 $986

per person

Mar 14 - Mar 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) 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 Central Chicago

[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 Central Chicago

![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! (3,498 reviews)

Great location! Nice view, good staff

Reviewed on Dec 17, 2025

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

![Homewood Suites by Hilton Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/2d5c8626_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Homewood Suites by Hilton Chicago Downtown South Loop

59 E. 11th Street Chicago IL

- 4 min drive from Michigan Avenue

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

8.6/10 Excellent! (2,131 reviews)

Cleanliness of the room

Reviewed on Dec 12, 2025

[](https://expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-South-Loop.h33387384.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

- 15 min walk from Michigan Avenue

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...

8.4/10 Very Good! (2,134 reviews)

Clean room. I didn’t mind the old door knobs I liked it. Smaller room than anticipated but it was nice and clean.

Reviewed on Dec 14, 2025

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

[See all 1,494 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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