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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,607
per person
Nov 20 - Nov 23
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Great hotel the staff was very helpful.
Very clean just overall a very impressive hotel and staff. Will definitely stay there again.
Reviewed on Sep 28, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,286
per person
Nov 15 - Nov 19
found 3 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,607
per person
Nov 20 - Nov 23
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Great hotel the staff was very helpful.
Very clean just overall a very impressive hotel and staff. Will definitely stay there again.
Reviewed on Sep 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips3 Night Pet-friendly holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,607
per person
Nov 20 - Nov 23
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Great hotel the staff was very helpful.
Very clean just overall a very impressive hotel and staff. Will definitely stay there again.
Reviewed on Sep 28, 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $2,132
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Great hotel the staff was very helpful.
Very clean just overall a very impressive hotel and staff. Will definitely stay there again.
Reviewed on Sep 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all tripsPet-friendly Hotels in Northwest Side
Sleeps 18 • 8BR • Game Room • Gym • Theater
Chicago IL
- 2 min walk from Portage Park
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! (9 reviews)
"Worked well for family visit thanks!"
Reviewed on Sep 14, 2026
Affordable Home- Near the 606
Chicago IL
- 7 min drive from Portage Park
Stay at this condo in Chicago. Enjoy free WiFi, laundry facilities, and patios. Popular attractions United Center and Wrigley Field are located nearby.
Theater • Game Room • Gym • Firepit • 4BR Home
Chicago IL
- 4 min drive from Portage Park
Stay at this vacation home in Chicago. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Portage Park and Frank Lloyd Wright ...
10/10 Exceptional! (7 reviews)
"We had a wonderful and relaxing stay, and we were able to get some much-needed rest. The place was beautiful, clean, and comfortable. The only thing I noticed is that it takes a while for the shower to get hot, and the hot water runs out pretty quickly. But overall, it was a great stay. We only wish ..."
Reviewed on Sep 28, 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.
Things to do
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
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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.
