Chicago Pet-friendly Holidays
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Top flight + Pet-friendly hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
per person
15 Aug - 18 Aug
found 6 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
This hotel is gorgeous. I love Kimpton properties and this one didn't disappoint. The restaurants are always good and the staff are always kind. The gym is fantastic, especially for a hotel! And the rooms are beautiful. I will come again for sure.
Reviewed on 30 Jun. 2025
Hilton Chicago
Downtown Chicago
per person
15 Aug - 18 Aug
found 6 hours ago
Return direct flight included
Auckland (AKL) 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 2 Jul. 2025
The Westin Michigan Avenue Chicago
Downtown Chicago
per person
15 Aug - 18 Aug
found 6 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
The staff were great, friendly and helpful! The area was great for walking to the lake, shopping. The only thing that was a disappointment, was that the bed was not very comfortable.
Reviewed on 2 Jul. 2025
5* Pet-friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
4 Night Pet-friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
per person
15 Aug - 18 Aug
found 6 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
This hotel is gorgeous. I love Kimpton properties and this one didn't disappoint. The restaurants are always good and the staff are always kind. The gym is fantastic, especially for a hotel! And the rooms are beautiful. I will come again for sure.
Reviewed on 30 Jun. 2025
Top Pet-friendly Chicago Hotels
The Royal Sonesta Chicago River North
505 N State Street, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant ...
9/10 Wonderful! (1,845 reviews)
Great place to Stay
"Most amazing fun here in the Resort. Loved all the Amenities 😃"
Reviewed on 2 Jul. 2025
Virgin Hotels Chicago
203 N Wabash Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. ...
9/10 Wonderful! (1,342 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 1 Jul. 2025
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,974 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 2 Jul. 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.