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 Arista
Price was CA $1,079, price is now CA $820 per person
CA $820
per person
May 5 - May 9
found 24 hours ago
Roundtrip flight included
New York (NYC) 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
Hotel 55 Chicago Downtown
Downtown Chicago
Price was CA $1,454, price is now CA $1,131 per person
CA $1,131
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (1,580 reviews)
Clean room, great location! Walked just about every where. Shower was amazing and room lights were on dimmers which is great for night time with children. I would definitely stay at this location again. Great price for a big city and location!
Reviewed on Mar 29, 2026
Hotel Lincoln
Lincoln Park
Price was CA $1,007, price is now CA $836 per person
CA $836
per person
May 5 - May 9
found 24 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
7.8/10 Good! (1,083 reviews)
Stayed at Hotel Lincoln and had a great experience overall! The location is fantastic—close to everything and perfect for exploring the area. The staff were incredibly friendly and welcoming, which really made the stay more enjoyable. The rooms were clean and comfortable. While the bathroom could use some updating, it didn’t take away from the overall positive experience. I’d definitely consider staying here again!
Reviewed on Mar 29, 2026
Hilton Chicago
Downtown Chicago
Price was CA $1,197, price is now CA $1,024 per person
CA $1,024
per person
May 1 - May 3
found 17 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
Room was clean but small. Extremely loud throughout the night hard to sleep not well insulated. Temperature fluctuates consistently throughout the day. High price on hidden charges and lost items using valet. Out dated elevators that need maintenance. Otherwise was good location to the heart of the city and very kind staff.
Reviewed on Mar 31, 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.
Hotel Arista
Price was CA $933, price is now CA $764 per person
CA $764
per person
Jun 5 - Jun 8
found 7 hours ago
Roundtrip flight included
Montreal (YMQ) 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
Hotel 55 Chicago Downtown
Downtown Chicago
Price was CA $1,454, price is now CA $1,131 per person
CA $1,131
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (1,580 reviews)
Clean room, great location! Walked just about every where. Shower was amazing and room lights were on dimmers which is great for night time with children. I would definitely stay at this location again. Great price for a big city and location!
Reviewed on Mar 29, 2026
Kinzie Hotel
Downtown Chicago
Price was CA $1,310, price is now CA $1,028 per person
CA $1,028
per person
May 1 - May 4
found 18 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
The staff was really great and the room was fine, nothing exceptional but nothing bad. The walls were thin and we when our neighbors pulled up their shades it was so loud it woke us up. We got a call at 7a with nobody on the other end, that also woke us up. haha
Reviewed on Mar 29, 2026
4 Night Pet-friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Downtown Chicago
Price was CA $927, price is now CA $696 per person
CA $696
per person
May 5 - May 9
found 24 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
The staff was really great and the room was fine, nothing exceptional but nothing bad. The walls were thin and we when our neighbors pulled up their shades it was so loud it woke us up. We got a call at 7a with nobody on the other end, that also woke us up. haha
Reviewed on Mar 29, 2026
Hotel 55 Chicago Downtown
Downtown Chicago
Price was CA $1,030, price is now CA $750 per person
CA $750
per person
May 5 - May 9
found 24 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (1,580 reviews)
Clean room, great location! Walked just about every where. Shower was amazing and room lights were on dimmers which is great for night time with children. I would definitely stay at this location again. Great price for a big city and location!
Reviewed on Mar 29, 2026
Hotel Arista
Price was CA $1,079, price is now CA $820 per person
CA $820
per person
May 5 - May 9
found 24 hours ago
Roundtrip flight included
New York (NYC) 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
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! (4,018 reviews)
My neck and my back are killing me and the staff forgot to give me my breakfast vouchers until my 3rd day. Then they refused to compensate me instead told me to go to complain to "Expedia". Cool. Great service. The lobby restaurant is decent. The staff there was cool. Sit at the bar and have a ...
Reviewed on Mar 31, 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! (5,051 reviews)
I stayed in the kitchenette with convenient microwave and silverware and plates so I can have small meals with my family. The bed was very comfortable. I think the sofa bed was OK. The hotel location is very convenient. Very close to all the destinations we planned my stay included parking in a self ...
Reviewed on Mar 31, 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! (2,388 reviews)
In the heart of Chicago could use more amenities, but of course space is limited
Reviewed on Mar 31, 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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