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.
Level Chicago - River North
Downtown Chicago
Price was CA $1,361, price is now CA $948 per person
CA $948
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (984 reviews)
I loved it very nice staff and it’s close to all the big things
Reviewed on May 15, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,145, price is now CA $1,440 per person
CA $1,440
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
Amazing hotel. I would stay again.
Reviewed on May 15, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,584, price is now CA $1,066 per person
CA $1,066
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.
Reviewed on May 14, 2026
The Wade
Downtown Chicago
Price was CA $2,205, price is now CA $1,494 per person
CA $1,494
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.4/10 Very Good! (1,825 reviews)
Lovely hotel, very modern and clean. Had fantastic views from the top floor. We were on floor 28 and the skyline was great. Bed very comfortable and it was expected from a 4* hotel. Chicago is a business city, reminded me of a bar man set as its high rised buildings and slightly darker from the shadows of these buildings. Locally there was a few cafes and coffee shops for easy reach for breakfast
Reviewed on May 11, 2026
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View all trips5* Pet-friendly holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
The Langham, Chicago
Downtown Chicago
Price was CA $1,820, price is now CA $1,330 per person
CA $1,330
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Great accommodation and staff attention
Reviewed on May 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,772, price is now CA $1,991 per person
CA $1,991
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I LOVE THIS HOTEL!!!
Reviewed on May 13, 2026
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View all trips3 Night Pet-friendly holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was CA $1,355, price is now CA $903 per person
CA $903
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!
Reviewed on May 13, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,584, price is now CA $1,066 per person
CA $1,066
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.
Reviewed on May 14, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,501, price is now CA $1,017 per person
CA $1,017
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Staff was very good, attentive. The property itself is in a great location, but the room showed some wear and tear - exposed drywall screws holding on bathroom door trim with some paint slapped on it, smelly sink, water damage and peeling paint on inside window sill, visually boring interior that looks like it's from the 1990's
Reviewed on May 12, 2026
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View all trips4 Night Pet-friendly holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was CA $2,052, price is now CA $1,266 per person
CA $1,266
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!
Reviewed on May 13, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,145, price is now CA $1,440 per person
CA $1,440
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
Amazing hotel. I would stay again.
Reviewed on May 15, 2026
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View all tripsPet-friendly Hotels in Northwest Side
Quiet Area - Revamped Basement
Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, a water park, and an in-room coffeemaker. Popular attractions United Center and Wrigley Field are located ...
10/10 Exceptional! (1 review)
Excellent apartment very clean and comfortable.
Reviewed on Apr 6, 2026
Sleeps 18 • 8BR • Game Room • Gym • Theater
Chicago IL
Stay at this vacation home in Chicago. Enjoy a pool table, an in-room coffeemaker, and air conditioning. Popular attractions Wrigley Field and Portage Park are ...
10/10 Exceptional! (1 review)
The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded ...
Reviewed on Apr 5, 2026
Cheerful 3 bedroom. Feels like home.
Chicago IL
Stay at this vacation home in Chicago. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Portage Park and Copernicus Center are located ...
9.8/10 Exceptional! (24 reviews)
The door code didn’t work half the time and took about 10 minutes to get in. Also the code changed during stay. The interior of place was ok but outside not great.
Reviewed on May 2, 2026
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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