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.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $639, price is now CA $425 per person
CA $425
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Our experience here was fantastic. We visited in August and the weather was superb. Everything was centralized. From shopping to dining and peace and quiet were abound. Just magnificent stay. The staff was friendly and informative. Thank you.
Reviewed on Sep. 4, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,093, price is now CA $1,377 per person
CA $1,377
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Québec (YQB) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was CA $1,004, price is now CA $674 per person
CA $674
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
8.2/10 Very Good! (2,121 reviews)
This hotel is everything anyone would ever need. While I was not fond of the price, it was a great choice and I also booked last minute, so the price is fair.
Reviewed on Sep. 5, 2025
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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 $2,093, price is now CA $1,377 per person
CA $1,377
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Québec (YQB) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
The Peninsula Chicago
Downtown Chicago
Price was CA $2,525, price is now CA $1,744 per person
CA $1,744
per person
Nov 27 - Dec 1
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,014 reviews)
Truly enjoyed our experience at this hotel. Staff very kind and helpful. Location was perfect because of its location on the Magnificent Mile and getting to other areas of interest in Chicago. The room was very comfortable and clean. Definitely recommend this hotel!
Reviewed on Sep. 4, 2025
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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.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was CA $894, price is now CA $580 per person
CA $580
per person
Nov 21 - Nov 24
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
Matthew at the front desk was great & he made our stay better than we could’ve expected. The food from the restaurant was amazing (highly recommend the wings) and the bartenders are wonderful! Our room was a dream! 100/10! ⭐️ We will definitely be returning for our next Chicago stay!
Reviewed on Sep. 5, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,093, price is now CA $1,377 per person
CA $1,377
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Québec (YQB) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
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.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,010, price is now CA $548 per person
CA $548
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Our experience here was fantastic. We visited in August and the weather was superb. Everything was centralized. From shopping to dining and peace and quiet were abound. Just magnificent stay. The staff was friendly and informative. Thank you.
Reviewed on Sep. 4, 2025
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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
Stay at this hotel in Chicago. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions United Center and Wrigley Field are located ...
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Chicago
Book a stay at this family-friendly vacation home in Chicago. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Wrigley Field and ...
Huge Projector and Designated Workspace - Near Wrigley!
Chicago
Stay at this condo in Chicago. Enjoy free WiFi, laundry facilities, and cable/satellite TV service. Popular attractions Wrigley Field and United Center are located ...
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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