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.
Hotel 55 Chicago Downtown
Downtown Chicago
Price was CA $877, price is now CA $712 per person
CA $712
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,580 reviews)
Great experience right price walking distance to get everything. If you ever wanted to visit the leaning tower of Pisa or spend your day like you are a superhero either going with gravity of fighting gravity up and downhill this is absolutely the place for you no joke your calf muscles will be insane from walking uphill from the door to the bed truly truly a great experience just got stronger leg muscles and a great view to boot
Reviewed on Mar 8, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $1,231, price is now CA $959 per person
CA $959
per person
Apr 16 - Apr 19
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
This was my first time ever staying at the Kimpton and it was absolutely amazing
Reviewed on Mar 8, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,516, price is now CA $2,061 per person
CA $2,061
per person
May 14 - May 17
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
The room was a little dated. I was surprised that you didn’t have CNBC as a TV choice, I thought the gym was dated and the WiFi was inadequate
Reviewed on Feb 28, 2026
Hotel Arista
Price was CA $913, price is now CA $751 per person
CA $751
per person
May 14 - May 17
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Room was clean, staff was friendly and parking was really easy. Very comfortable stay.
Reviewed on Mar 5, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,089, price is now CA $908 per person
CA $908
per person
Apr 16 - Apr 19
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
5* Pet-friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,516, price is now CA $2,061 per person
CA $2,061
per person
May 14 - May 17
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
The room was a little dated. I was surprised that you didn’t have CNBC as a TV choice, I thought the gym was dated and the WiFi was inadequate
Reviewed on Feb 28, 2026
3 Night Pet-friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $955, price is now CA $744 per person
CA $744
per person
Apr 16 - Apr 19
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,476 reviews)
The rooms are a bit small
The beds are super high.
The hotel is chic and modern.
Reviewed on Mar 12, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $1,231, price is now CA $959 per person
CA $959
per person
Apr 16 - Apr 19
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
This was my first time ever staying at the Kimpton and it was absolutely amazing
Reviewed on Mar 8, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,464, price is now CA $1,163 per person
CA $1,163
per person
May 14 - May 17
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,016 reviews)
Exceptional hotel perfectly located. Theaters and museums within blocks as well as the iconic Bean and Lakeshore Trail. The hotel has historic charm with pineapple touches that make you smile. The guest services is exceptional. They made my birthday extra special. I appreciate the free coffee every morning. Cannot beat the 12:00 checkout and it's pet friendly.
Reviewed on Mar 13, 2026
4 Night Pet-friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel 55 Chicago Downtown
Downtown Chicago
Price was CA $877, price is now CA $712 per person
CA $712
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,580 reviews)
Great experience right price walking distance to get everything. If you ever wanted to visit the leaning tower of Pisa or spend your day like you are a superhero either going with gravity of fighting gravity up and downhill this is absolutely the place for you no joke your calf muscles will be insane from walking uphill from the door to the bed truly truly a great experience just got stronger leg muscles and a great view to boot
Reviewed on Mar 8, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $2,220, price is now CA $1,751 per person
CA $1,751
per person
May 14 - May 18
found 22 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,016 reviews)
Exceptional hotel perfectly located. Theaters and museums within blocks as well as the iconic Bean and Lakeshore Trail. The hotel has historic charm with pineapple touches that make you smile. The guest services is exceptional. They made my birthday extra special. I appreciate the free coffee every morning. Cannot beat the 12:00 checkout and it's pet friendly.
Reviewed on Mar 13, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $2,348, price is now CA $1,896 per person
CA $1,896
per person
May 14 - May 18
found 22 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
Pet-friendly Hotels in Chicago
Hilton Chicago
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,675 reviews)
The location was great we walked to the Shedd aquarium in no time. The hotel was nice, we found it really irritating that we were constantly asked to join Hilton rewards by the staff standing at the elevators. Also you can not control the room temperature it was so hot and their solution was to open ...
Reviewed on Mar 13, 2026
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! (3,909 reviews)
location and room met expectations
Reviewed on Mar 13, 2026
Aloft Chicago Mag Mile
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,136 reviews)
Good location and value for the price
Reviewed on Mar 12, 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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