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Flight and Pet-friendly hotel deals in Southeast Wisconsin

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

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Avenues West

CA $1,049

per person

Jun 15 - Jun 17

found 22 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Milwaukee (MKE)

9/10 Wonderful! (1,329 reviews)

Room was great. Bed was very comfortable and great view

Reviewed on Apr 27, 2026

The Pfister Hotel

Downtown Milwaukee

CA $1,587

per person

Jun 18 - Jun 21

found 14 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Milwaukee (MKE)

9.6/10 Exceptional! (2,083 reviews)

Beautiful and elegant. Great food. Fun rooftop bar. Wonderful spa experience, both pedicure and massage. I’ll definitely be back. We’re already planning our next visit here.

Reviewed on Apr 22, 2026

The Iron Horse Hotel

Fifth Ward

CA $1,468

per person

Jun 18 - Jun 21

found 14 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Milwaukee (MKE)

9.2/10 Wonderful! (1,067 reviews)

Staff was very nice and helpful. They need more snack options to quickly buy.

Reviewed on Apr 24, 2026

Kimpton Journeyman Hotel by IHG

Downtown Milwaukee

CA $1,755

per person

Jun 18 - Jun 21

found 14 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Milwaukee (MKE)

9.4/10 Exceptional! (979 reviews)

Great place and stay. Walking distance to so much fun places.

Reviewed on Apr 3, 2026

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3 Night Pet-friendly holidays in Southeast Wisconsin

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

The Iron Horse Hotel

Fifth Ward

CA $1,468

per person

Jun 18 - Jun 21

found 14 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Milwaukee (MKE)

9.2/10 Wonderful! (1,067 reviews)

Staff was very nice and helpful. They need more snack options to quickly buy.

Reviewed on Apr 24, 2026

The Pfister Hotel

Downtown Milwaukee

CA $1,587

per person

Jun 18 - Jun 21

found 14 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Milwaukee (MKE)

9.6/10 Exceptional! (2,083 reviews)

Beautiful and elegant. Great food. Fun rooftop bar. Wonderful spa experience, both pedicure and massage. I’ll definitely be back. We’re already planning our next visit here.

Reviewed on Apr 22, 2026

Kimpton Journeyman Hotel by IHG

Downtown Milwaukee

CA $1,755

per person

Jun 18 - Jun 21

found 14 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Milwaukee (MKE)

9.4/10 Exceptional! (979 reviews)

Great place and stay. Walking distance to so much fun places.

Reviewed on Apr 3, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southeast Wisconsin

View all trips

Pet-friendly Hotels in Southeast Wisconsin

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

6 min drive from American Family Field

Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...

9.6/10 Exceptional! (2,186 reviews)

Clean. Quiet. Check in was quick. Parking was ready. Drinks in the bar were great. The staff is awesome. Have stayed here several times and stay again!

Reviewed on Apr 27, 2026

The Iron Horse Hotel

500 W Florida Street Milwaukee WI

5 min drive from American Family Field

Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

9.2/10 Wonderful! (1,076 reviews)

My room was not clean when I arrived at 10:30pm. The receptionist and bar staff were amazing, but because the hotel was sold out we were sent to another hotel. That hotel room was much smaller, smelled like sewage, and had maintenance issues. The staff were amazing, but if management thinks that ...

Reviewed on Apr 25, 2026

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

7 min drive from American Family Field

Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...

9.6/10 Exceptional! (2,080 reviews)

The pool

Reviewed on Apr 25, 2026

See all 2,436 properties in Southeast Wisconsin

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.