
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
Price was $287, price is now $225 per person
$225
per person
Dec 25 - Dec 27
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
8.4/10 Very Good! (2,261 reviews)
Could use some thicker walls! Felt like the dinosaur kids next door were in my room!
Reviewed on Oct 24, 2025

The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,378, price is now $629 per person
$629
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
Hotel in great location, would stay again
Reviewed on Oct 19, 2025

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,197, price is now $815 per person
$815
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025

Kimpton Gray Hotel by IHG
Downtown Chicago
Price was $707, price is now $519 per person
$519
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (1,008 reviews)
I was not impressed overall and honestly expected much more from a 4.5-star hotel in Chicago.
Check-in with the concierge was smooth, and the staff was polite and efficient, which I appreciated. However, the condition of the common areas left a lot to be desired. The hallways and entrance carpets looked unclean, and the elevators also did not feel particularly clean. The lighting in the entrance area was poor and gave off a rather uninviting vibe.
Service was inconsistent: I requested a blanket one night, and it took nearly an hour to arrive. Access to water was inconvenient—only two bottles were provided, and there weren’t enough fountains. Offering reusable bottles for guests to refill would be a much better experience.
The in-room amenities were disappointing. Towels looked worn and old, the shower had weak water pressure and limited flow, and it was unclear what room service was available, if any.
Overall, while the staff was professional, the property itself did not live up to the standard I was expecting. Definitely not on par with what a 4.5-star rating suggests. Will not return and certainly do not reccomend.
Reviewed on Sep 28, 2025

Kinzie Hotel
Downtown Chicago
Price was $531, price is now $427 per person
$427
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Kansas City (MCI) to Chicago (ORD)
9.2/10 Wonderful! (1,936 reviews)
There’s nothing really special about this hotel honestly. I’ve stayed in better hotels for other chains and would prefer those over this one.
Our floor reeked of weed every day we were there, and none of the staff seemed to care or do anything about it even after being notified.
Overall, nothing to write home about. It’s super loud outside between cars, and emergency vehicles driving by every 5-10 minutes. If I knew this prior, I wouldn’t have stayed here
Reviewed on Oct 24, 2025
5* Pet-friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,197, price is now $815 per person
$815
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
3 Night Pet-friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.


Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,197, price is now $815 per person
$815
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025

4 Night Pet-friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.


The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,378, price is now $629 per person
$629
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
Hotel in great location, would stay again
Reviewed on Oct 19, 2025

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,298, price is now $788 per person
$788
per person
Dec 25 - Dec 29
found 2 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
Top Pet-friendly Chicago Hotels

Freehand Chicago
19 East Ohio Street, Chicago, IL
This pet-friendly, city-center hotel welcomes dogs for an additional fee. Nearby Millennium Park is a good place to stretch your legs if you need a walk.
7.8/10 Good! (2,524 reviews)
Everything was great
Reviewed on Oct 24, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Dogs and cats are welcome (fees apply) at this pet-friendly, city-center hotel. If you'd like to stretch your legs, look no further than nearby Lincoln ...
8.8/10 Excellent! (3,145 reviews)
Hotel was everything i needed for a work trip
Reviewed on Oct 25, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
This pet-friendly, city-center hotel welcomes dogs and cats for an additional fee. Nearby Millennium Park is a good place to stretch your legs if you need a ...
8.4/10 Very Good! (4,105 reviews)
Pleasant comfortable stay
Reviewed on Oct 25, 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.
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