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 – 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
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! (3,319 reviews)
2 blocks off Michigan ave, 1 block to the river, and great views of Lake Michigan. Staff was very helpful and kind.
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! (2,505 reviews)
Amazing hotel. I would stay again.
Reviewed on May 15, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,809, price is now CA $1,239 per person
CA $1,239
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy.
My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.
Reviewed on May 12, 2026
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See all available trips from Columbus to Northwest Side
View all trips5* Pet-friendly holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
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.
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)
Suite was very nice! Clean and quiet and we got a free upgrade. 2 bedrooms, 2 full baths, a kitchen and living space. There was also laundry in our suite!
Reviewed on May 15, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,732, price is now CA $1,829 per person
CA $1,829
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,505 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
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
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! (3,319 reviews)
2 blocks off Michigan ave, 1 block to the river, and great views of Lake Michigan. Staff was very helpful and kind.
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! (2,505 reviews)
Amazing hotel. I would stay again.
Reviewed on May 15, 2026
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See all available trips from Columbus to Northwest Side
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
