
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 ¥105,332, price is now ¥75,812 per person
¥75,812
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
8.4/10 Very Good! (2,261 reviews)
Location is really great but building needs a lot of updating. Didn’t get the room serviced the whole 3 nights but perhaps we had to call for them to do it. I had picked a room facing out and they changed it to one facing a wall. We didn’t bother complaining since we spent most of the time exploring the city. Breakfast buffet was very expensive but not really worth it.
Reviewed on Oct 22, 2025

21c Museum Hotel Chicago
Downtown Chicago
Price was ¥110,637, price is now ¥83,820 per person
¥83,820
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
8.8/10 Excellent! (1,626 reviews)
The staff was great, the rooms comfortable. My only complaint was the espresso machines did not work well at all. Very confusing first, then the machine would crush the pods so we used 6 pods to get 2 cups of coffee, not very efficient.
Reviewed on Oct 21, 2025

Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ¥235,763, price is now ¥203,670 per person
¥203,670
per person
Nov 27 - Dec 2
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) 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 ¥235,317, price is now ¥204,538 per person
¥204,538
per person
Nov 27 - Dec 2
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,936 reviews)
Hotel is conveniently located near main tourist attractions downtown. Room was spacious and comfortable. It's a little noisy, but not unexpected for inner city. Staff was very friendly and helpful.
Reviewed on Oct 20, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥213,296, price is now ¥191,220 per person
¥191,220
per person
Nov 27 - Dec 2
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,137 reviews)
The room I was in was smaller than expected but was clean and well furnished. All of the staff that I interacted with were polite, courteous and professional at all times. Most things in Chicago are within walking distance from this hotel so it is well located in this respect. A couple of theatres are very close, one next-door, so handy in this respect. A good hotel with great staff.
Reviewed on Oct 22, 2025
4 Night Pet-friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.

The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Price was ¥205,747, price is now ¥196,340 per person
¥196,340
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (3,657 reviews)
The location was very good. The included breakfast was good and appreciated. The only complaint was the noisy aircon in the room.
Reviewed on Oct 22, 2025

Hilton Chicago
Downtown Chicago
Price was ¥227,426, price is now ¥209,668 per person
¥209,668
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,261 reviews)
Location is really great but building needs a lot of updating. Didn’t get the room serviced the whole 3 nights but perhaps we had to call for them to do it. I had picked a room facing out and they changed it to one facing a wall. We didn’t bother complaining since we spent most of the time exploring the city. Breakfast buffet was very expensive but not really worth it.
Reviewed on Oct 22, 2025

Kinzie Hotel
Downtown Chicago
Price was ¥213,268, price is now ¥201,548 per person
¥201,548
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,936 reviews)
Hotel is conveniently located near main tourist attractions downtown. Room was spacious and comfortable. It's a little noisy, but not unexpected for inner city. Staff was very friendly and helpful.
Reviewed on Oct 20, 2025
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! (2,200 reviews)
It was a short stay for me, but I wished I could have stayed longer. Very clean and the staff were super friendly. The lobby is small and very cozy. The whole vibe is just so inviting. The location is also very central.
Reviewed on Oct 19, 2025

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! (1,385 reviews)
Great stay and location
Reviewed on Oct 15, 2025

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! (2,276 reviews)
Just one complaint, the rooms can use a makeover, especially the carpet.
Reviewed on Oct 19, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.