Great Lakes Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,812, price is now CA $1,419 per person
CA $1,419
per person
Jun 8 - Jun 12
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Wonderful hotel. Great location at a great price.
Reviewed on Apr 1, 2026
The Iron Horse Hotel
Fifth Ward
Price was CA $1,667, price is now CA $1,385 per person
CA $1,385
per person
Jun 21 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.2/10 Wonderful! (1,046 reviews)
Great location, spacious room and friendly staff! Would definitely come back
Reviewed on Apr 6, 2026
Hilton Milwaukee
Westown
Price was CA $1,351, price is now CA $1,166 per person
CA $1,166
per person
May 15 - May 17
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
8.6/10 Excellent! (1,131 reviews)
Excellent hotel, beautiful rooms and great restaurants on site and nearby.
Reviewed on Apr 5, 2026
Hilton Chicago
Downtown Chicago
Price was CA $1,165, price is now CA $1,018 per person
CA $1,018
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.6/10 Excellent! (2,718 reviews)
I love the location. People always s friendly and allow pets. Unfortunately, we never received room cleaning in 4 nights! And the swimming pool was too dirty
Reviewed on Apr 6, 2026
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See all available trips from Columbus to Great Lakes
View all trips3 Night Pet-friendly holidays in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Downtown Chicago
Price was CA $1,034, price is now CA $851 per person
CA $851
per person
May 12 - May 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,718 reviews)
I love the location. People always s friendly and allow pets. Unfortunately, we never received room cleaning in 4 nights! And the swimming pool was too dirty
Reviewed on Apr 6, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,323, price is now CA $1,093 per person
CA $1,093
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Wonderful hotel. Great location at a great price.
Reviewed on Apr 1, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Lakes
View all trips4 Night Pet-friendly holidays in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,812, price is now CA $1,419 per person
CA $1,419
per person
Jun 8 - Jun 12
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Wonderful hotel. Great location at a great price.
Reviewed on Apr 1, 2026
Hilton Chicago
Downtown Chicago
Price was CA $1,499, price is now CA $1,240 per person
CA $1,240
per person
May 12 - May 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
8.6/10 Excellent! (2,718 reviews)
I love the location. People always s friendly and allow pets. Unfortunately, we never received room cleaning in 4 nights! And the swimming pool was too dirty
Reviewed on Apr 6, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Lakes
View all tripsPet-friendly Hotels in Great Lakes
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! (4,077 reviews)
Didn’t like the bed so much and the couch wasn’t comfy but overall I would stay again
Reviewed on Apr 7, 2026
Chelsea Hotel, Toronto
33 Gerrard St W Toronto ON
Book a stay at this family-friendly hotel in Toronto. Enjoy free WiFi, 2 indoor pools, and 2 restaurants. Our guests praise the pool and the restaurant in our ...
8.4/10 Very Good! (14,411 reviews)
Property is looking rough and old. Definitely not the "delta" chelsea of the old days. good location to everything though.
Reviewed on Apr 7, 2026
One King West Hotel & Residence
1 King Street West Toronto ON
Book a stay at this business-friendly hotel in Toronto. Enjoy free WiFi, room service, and a fitness center. Our guests praise the restaurant and the helpful ...
9.4/10 Exceptional! (7,456 reviews)
No
Reviewed on Apr 7, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
