
Far North Side Pet-friendly Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Flight and Pet-friendly hotel deals in Far North Side
Price found within the past 48 hours. Click for updated prices.


Park Hyatt Chicago
Downtown Chicago
Price was CA $3,871, price is now CA $2,284 per person
CA $2,284
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,354, price is now CA $817 per person
CA $817
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.
Reviewed on Aug. 17, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,851, price is now CA $1,121 per person
CA $1,121
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug. 19, 2025

The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,069, price is now CA $664 per person
CA $664
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Modern comfortable hotel in a good location close to downtown parks and museums Friendly helpful staff
Many good restaurants nearby
Reviewed on Aug. 19, 2025
Don't see what you're looking for?
See all available trips from Columbus to Far North Side
View all trips5* Pet-friendly holidays in Far North Side
Price found within the past 48 hours. Click for updated prices.


Park Hyatt Chicago
Downtown Chicago
Price was CA $3,871, price is now CA $2,284 per person
CA $2,284
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,851, price is now CA $1,121 per person
CA $1,121
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug. 19, 2025
Don't see what you're looking for?
See all available trips from Columbus to Far North Side
View all trips3 Night Pet-friendly holidays in Far North Side
Price found within the past 48 hours. Click for updated prices.

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,354, price is now CA $817 per person
CA $817
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.
Reviewed on Aug. 17, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,851, price is now CA $1,121 per person
CA $1,121
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug. 19, 2025

Park Hyatt Chicago
Downtown Chicago
Price was CA $1,656, price is now CA $1,018 per person
CA $1,018
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025
Don't see what you're looking for?
See all available trips from Columbus to Far North Side
View all trips4 Night Pet-friendly holidays in Far North Side
Price found within the past 48 hours. Click for updated prices.

Park Hyatt Chicago
Downtown Chicago
Price was CA $2,804, price is now CA $1,634 per person
CA $1,634
per person
Oct 20 - Oct 24
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $2,865, price is now CA $1,748 per person
CA $1,748
per person
Oct 9 - Oct 13
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!
Reviewed on Aug. 18, 2025

The Langham, Chicago
Downtown Chicago
Price was CA $3,125, price is now CA $1,932 per person
CA $1,932
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.8/10 Exceptional! (1,004 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 Far North Side
View all tripsPet-friendly Hotels in Far North Side

Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.2/10 Very Good! (2,096 reviews)
"The room was clean and the bed was comfortable. The staff was courteous and helpful."
Reviewed on Aug. 18, 2025

Holiday Inn Chicago O'Hare Area by IHG
5615 North Cumberland Avenue, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.6/10 Good! (1,002 reviews)
"Property is convenient near the airport. The hotel also has a shuttle to the airport. The rooms are clean. I stay there once a year for my business trip."
Reviewed on Aug. 16, 2025

The Rose Chicago, Tapestry Collection by Hilton
5200 Pearl Street, Rosemont, IL
Stay at this 4-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
9.2/10 Wonderful! (1,001 reviews)
"nice"
Reviewed on Aug. 16, 2025
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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.