Central Chicago Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,155, price is now CA $766 per person
CA $766
per person
Jun 8 - Jun 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was perfect. The staff are really friendly and helpful. Love it!!! Definitely I'll come back
Reviewed on Apr 1, 2026
Kinzie Hotel
Downtown Chicago
Price was CA $1,313, price is now CA $974 per person
CA $974
per person
May 5 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
The staff was really great and the room was fine, nothing exceptional but nothing bad. The walls were thin and we when our neighbors pulled up their shades it was so loud it woke us up. We got a call at 7a with nobody on the other end, that also woke us up. haha
Reviewed on Mar 29, 2026
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View all trips5* Pet-friendly holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,949, price is now CA $1,568 per person
CA $1,568
per person
Jun 3 - Jun 6
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
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View all trips3 Night Pet-friendly holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,543, price is now CA $1,017 per person
CA $1,017
per person
Jun 3 - Jun 6
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Comfortable, clean room, and you can't beat the view! My favorite thing is relaxing on the chaise lounge, watching the sun rise over Lake Michigan! The food at Lirica is awesome, too.
Reviewed on Apr 1, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,613, price is now CA $1,020 per person
CA $1,020
per person
Jun 3 - Jun 6
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was perfect. The staff are really friendly and helpful. Love it!!! Definitely I'll come back
Reviewed on Apr 1, 2026
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See all available trips from Columbus to Central Chicago
View all trips4 Night Pet-friendly holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,964, price is now CA $1,351 per person
CA $1,351
per person
Jun 27 - Jul 1
just found
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was perfect. The staff are really friendly and helpful. Love it!!! Definitely I'll come back
Reviewed on Apr 1, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,287, price is now CA $1,544 per person
CA $1,544
per person
Jun 27 - Jul 1
just found
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Comfortable, clean room, and you can't beat the view! My favorite thing is relaxing on the chaise lounge, watching the sun rise over Lake Michigan! The food at Lirica is awesome, too.
Reviewed on Apr 1, 2026
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View all tripsPet-friendly Hotels in Central Chicago
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,032 reviews)
Overall a great place. My only issue was that they charged us for 3 nights of valet @82.00, but we only had a car there for one night.
Reviewed on Apr 1, 2026
River Hotel
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,041 reviews)
I stayed in the kitchenette with convenient microwave and silverware and plates so I can have small meals with my family. The bed was very comfortable. I think the sofa bed was OK. The hotel location is very convenient. Very close to all the destinations we planned my stay included parking in a self ...
Reviewed on Mar 31, 2026
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
8.8/10 Excellent! (2,388 reviews)
The place is nice. Didn’t experience the whole sta due to early check out.
Reviewed on Apr 1, 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.
