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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,075
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 2026
The Peninsula Chicago
Downtown Chicago
CA $2,564
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class
Reviewed on Oct 1, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
CA $1,199
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
I stayed in a room at the back, every morning at 5:30 am trucks and dumpsters were moved, noise so loud it woke me up.
Was charged an amenity fee and there were really mo amenities. Breakfast sucked both days in first floor restaurant. Won't stay again.
Reviewed on Oct 1, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,676
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 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
CA $1,075
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 2026
The Peninsula Chicago
Downtown Chicago
CA $2,564
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class
Reviewed on Oct 1, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,676
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,487
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,892
per person
Nov 8 - Nov 12
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 2026
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See all available trips from Columbus to Central Chicago
View all tripsPet-friendly Hotels in Central Chicago
River Hotel
75 East Wacker Drive Chicago IL
- 6 min drive from McCormick Place
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 ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
- 9 min drive from McCormick Place
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very good! (2,398 reviews)
"I did not like this hotel despite being in a great neighborhood. Noisy, you can hear your neighbors, decor insipid in beige/gray, marijuana smoke coming from emergency stairwell into room, no water in room nor any coffee or room service."
Reviewed on Oct 3, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
- 8 min drive from McCormick Place
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very good! (2,297 reviews)
"The room was very spacious. The location of the hotel was great. The breakfast was delicious. We will definitely stay here again!"
Reviewed on Oct 3, 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.
