Chicago Pet-friendly Vacations
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Top Pet-friendly vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Downtown Chicago
per person
Aug 18 - Aug 25
found 20 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.4/10 Very Good! (1,950 reviews)
The property was very nice until we got to the room. The room seemed more dark and dingy. Very expensive for the quality of the room. Staff were extremely nice and the hotel was more central to different parks and modes of transportation.
Reviewed on 2025/7/2
Virgin Hotels Chicago
Downtown Chicago
per person
Aug 18 - Aug 25
found 20 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (1,333 reviews)
We really enjoyed our stay but felt the price was too high for the size of the room, and the lack of places to sit in the room. Only one chair.
Reviewed on 2025/7/1
The Royal Sonesta Chicago River North
Downtown Chicago
per person
Aug 18 - Aug 25
found 20 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (1,822 reviews)
Advertised a pool and breakfast was included. The pool was closed and there was no breakfast. I was offered a credit for breakfast at the restaurant, used it, and then was billed for it.
Reviewed on 2025/7/1
Top Pet-friendly Chicago Hotels
The Royal Sonesta Chicago River North
505 N State Street, Chicago, IL
Dogs and cats are welcome (fees apply) at this luxury hotel offering pet-friendly amenities, like food and water bowls. If you need a walk during your stay, ...
9/10 Wonderful! (1,848 reviews)
Great place to Stay
"Most amazing fun here in the Resort. Loved all the Amenities 😃"
Reviewed on 2025/7/2
Virgin Hotels Chicago
203 N Wabash Ave, Chicago, IL
Four-legged friends stay free at this luxury, city-center hotel, which offers pet-friendly amenities, like food and water bowls. While you're here, visit nearby ...
9/10 Wonderful! (1,340 reviews)
"Love the Virgin brand. However, Loading and unloading was terribly managed and spaces in front of hotel were taken by valet of Vip vehicles. Also, there were so many no guests that were attending a roof top club that elecators were all full. Didnt seem very sade nor well managed."
Reviewed on 2025/6/28
Hilton Chicago
720 S Michigan Ave, Chicago, IL
A city-center getaway awaits at this historic hotel, where pets are welcome (fees apply). Need a walk during your pet-friendly stay? Stretch your legs at nearby ...
8.4/10 Very Good! (1,971 reviews)
"The hotel was clean and had nice amenities, and we appreciated the location. It was very easy to walk to the water front or museums, and there are bus and metro stops nearby for longer journeys. Our biggest gripe was that there was no way to access streaming services through the in-room TV, but that’s ..."
Reviewed on 2025/7/1
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.