Chicago Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,214, price is now CA $953 per person
CA $953
per person
Jun 1 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Hotel was clean. Staff was friendly. Breakfast from hotel wasn’t bad but pricey. We had an issue with the AC in our room and had to move rooms mid stay. Staff took care of the issue but didn’t do anything to compensate for the inconvenience. I wish they had coffee makers or better coffee options within the hotel.
Reviewed on Mar 27, 2026
Hotel Arista
Price was CA $1,425, price is now CA $1,058 per person
CA $1,058
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
Our room was spacious, clean and well appointed. I love a bathroom with good lighting and the tv in the vanity mirror was fantastic to catch the morning news as we got ready!!
The staff was exceptional. From check in, to drinks at the bar, to room service, everyone was incredibly friendly and professional. I highly recommend Hotel Arista.
Reviewed on Mar 24, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $2,127, price is now CA $1,601 per person
CA $1,601
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
Great property, so many cute details in this historic hotel. The staff was friendly, the property was pristine, and it’s close to so many things to visit and do in Chicago. A close walk to Millennium Park, and many shops.
Reviewed on Mar 27, 2026
Hilton Chicago
Downtown Chicago
Price was CA $3,098, price is now CA $2,706 per person
CA $2,706
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
The breakfast was great.
Rooms were spotless and the double room had two bathrooms that was great when sharing with a friend
Reviewed on Mar 27, 2026
5* Pet-friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
3 Night Pet-friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,214, price is now CA $953 per person
CA $953
per person
Jun 1 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Hotel was clean. Staff was friendly. Breakfast from hotel wasn’t bad but pricey. We had an issue with the AC in our room and had to move rooms mid stay. Staff took care of the issue but didn’t do anything to compensate for the inconvenience. I wish they had coffee makers or better coffee options within the hotel.
Reviewed on Mar 27, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $2,127, price is now CA $1,601 per person
CA $1,601
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
Great property, so many cute details in this historic hotel. The staff was friendly, the property was pristine, and it’s close to so many things to visit and do in Chicago. A close walk to Millennium Park, and many shops.
Reviewed on Mar 27, 2026
4 Night Pet-friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $2,479, price is now CA $2,061 per person
CA $2,061
per person
May 14 - May 18
found 2 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
Hotel 55 Chicago Downtown
Downtown Chicago
Price was CA $2,066, price is now CA $1,791 per person
CA $1,791
per person
May 15 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (1,580 reviews)
Great hotel, Great staff, Great environment! Only complaint I have is $80 for parking is too high but I would definitely stay again and recommend it to others
Reviewed on Mar 23, 2026
Pet-friendly Hotels in Chicago
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (3,996 reviews)
We stayed 5 days our room was cleaned each day! We had a great stay!
Reviewed on Mar 28, 2026
River Hotel
75 East Wacker Drive Chicago IL
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 ...
8.8/10 Excellent! (5,032 reviews)
I didn’t use them.
Reviewed on Mar 27, 2026
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
8.8/10 Excellent! (2,379 reviews)
Everything was good except for not having access to the outdoor space. When we were booking the hotel the outdoor area was one of the reasons the pulled us to stay there. It was not stated that it was unavailable for the season. The pool being closed i get it, but the rest that was featured in the ...
Reviewed on Mar 26, 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.
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