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Flight and Pet-friendly hotel deals in Great Lakes

Price found within the past 48 hours. Click for updated prices.

Hilton Milwaukee

Westown

CA $1,166

per person

May 15 - May 17

found 1 day 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

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $1,389

per person

Jun 7 - Jun 10

found 3 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) 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

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

L7 Chicago by LOTTE

Downtown Chicago

CA $2,033

per person

Jun 7 - Jun 10

found 3 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

9.6/10 Exceptional! (3,846 reviews)

Very clean hotel. Staff was helpful and friendly.

Reviewed on Apr 6, 2026

Kimpton Gray Hotel by IHG

Downtown Chicago

CA $1,322

per person

May 22 - May 25

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

9.4/10 Exceptional! (1,001 reviews)

The room was clean, comfortable, and well organized The location was perfect, close to restaurants and attractions

Reviewed on Mar 15, 2026

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3 Night Pet-friendly holidays in Great Lakes

Price found within the past 48 hours. Click for updated prices.

Hilton Chicago

Downtown Chicago

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

CA $1,389

per person

Jun 7 - Jun 10

found 3 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

9.4/10 Exceptional! (1,026 reviews)

Wonderful hotel. Great location at a great price.

Reviewed on Apr 1, 2026

L7 Chicago by LOTTE

Downtown Chicago

CA $2,033

per person

Jun 7 - Jun 10

found 3 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

9.6/10 Exceptional! (3,846 reviews)

Very clean hotel. Staff was helpful and friendly.

Reviewed on Apr 6, 2026

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4 Night Pet-friendly holidays in Great Lakes

Price found within the past 48 hours. Click for updated prices.

Sports Illustrated Resorts Chicago

Downtown Chicago

CA $1,027

per person

May 12 - May 16

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Chicago (ORD)

9.2/10 Wonderful! (1,409 reviews)

Very friendly staff, great location.

Reviewed on Apr 6, 2026

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $1,505

per person

May 12 - May 16

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Chicago (ORD)

9.4/10 Exceptional! (1,026 reviews)

Wonderful hotel. Great location at a great price.

Reviewed on Apr 1, 2026

L7 Chicago by LOTTE

Downtown Chicago

CA $1,180

per person

May 12 - May 16

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Chicago (ORD)

9.6/10 Exceptional! (3,846 reviews)

Very clean hotel. Staff was helpful and friendly.

Reviewed on Apr 6, 2026

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See all available trips from Columbus to Great Lakes

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Pet-friendly Hotels in Great Lakes

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

16 hours drive from Lake Superior

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! (4,083 reviews)

Great location for a great

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! (14,417 reviews)

The Hotel is really showing it's age. Cumbling concrete and peeling wall paper in the bathroom. However, this hotel is really close to the Toronto General Hospital.

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! (7,465 reviews)

Excellent restaurant.

Reviewed on Apr 7, 2026

See all 80,600 properties in Great Lakes

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.