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Flight and Cheap hotel deals in Southeast Wisconsin

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

The Ingleside Hotel

CA $881

per person

Jun 15 - Jun 18

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Milwaukee (MKE)

8.6/10 Excellent! (792 reviews)

Wonderful hotel and perfect room. I loved staying there.

Reviewed on May 5, 2026

Saint Kate - The Arts Hotel

Downtown Milwaukee

CA $1,657

per person

Jul 1 - Jul 4

found 1 day ago

Roundtrip flight included

Charlottetown (YYG) to Milwaukee (MKE)

9.8/10 Exceptional! (2,639 reviews)

Enjoyed our stay! Room was wonderful, clean and very comfortable. We had an event at the Pabst theater and we were able to get there without leaving the building. Many restaurants around either walking distance or short Uber ride away. Would definitely stay again.

Reviewed on May 8, 2026

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Avenues West

CA $1,347

per person

Jun 15 - Jun 18

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Milwaukee (MKE)

9/10 Wonderful! (1,322 reviews)

The hotel staff was very friendly and welcoming. We enjoyed the charm of the hotel and our room!

Reviewed on May 9, 2026

The Iron Horse Hotel

Fifth Ward

CA $1,268

per person

Jun 23 - Jun 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.2/10 Wonderful! (1,099 reviews)

We loved our stay .. everything was great. The staff was amazing. The bar and food was wonderful. Would go back again and refer to family & friends

Reviewed on May 8, 2026

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3 Night Cheap holidays in Southeast Wisconsin

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

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Avenues West

CA $1,347

per person

Jun 15 - Jun 18

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Milwaukee (MKE)

9/10 Wonderful! (1,322 reviews)

The hotel staff was very friendly and welcoming. We enjoyed the charm of the hotel and our room!

Reviewed on May 9, 2026

Saint Kate - The Arts Hotel

Downtown Milwaukee

CA $1,657

per person

Jul 1 - Jul 4

found 1 day ago

Roundtrip flight included

Charlottetown (YYG) to Milwaukee (MKE)

9.8/10 Exceptional! (2,639 reviews)

Enjoyed our stay! Room was wonderful, clean and very comfortable. We had an event at the Pabst theater and we were able to get there without leaving the building. Many restaurants around either walking distance or short Uber ride away. Would definitely stay again.

Reviewed on May 8, 2026

The Iron Horse Hotel

Fifth Ward

CA $1,645

per person

Jul 1 - Jul 4

found 1 day ago

Roundtrip flight included

Charlottetown (YYG) to Milwaukee (MKE)

9.2/10 Wonderful! (1,099 reviews)

We loved our stay .. everything was great. The staff was amazing. The bar and food was wonderful. Would go back again and refer to family & friends

Reviewed on May 8, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southeast Wisconsin

View all trips

Cheap Hotels in Southeast Wisconsin

Sleep Inn & Suites Milwaukee Airport

4600 S 6th St Milwaukee WI

12 min drive from American Family Field

Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...

8.4/10 Very Good! (1,221 reviews)

The property was clean

Reviewed on May 4, 2026

Best Western Plus Milwaukee Airport Hotel & Conference Ctr

5105 S Howell Avenue Milwaukee WI

14 min drive from American Family Field

Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff ...

7.6/10 Good! (1,102 reviews)

Loved the pool and the breakfast buffet, room was very clean and environmentally friendly.

Reviewed on May 8, 2026

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! (2,207 reviews)

We found this hotel had very helpful staff. Our room was out of kleenex, I mentioned this to someone at the front desk and they resolved the problem very quickly. They had free meals, which were good. We ate dinner and breakfast. We were not familiar with the downtown Milwaukee area, so thanks to ...

Reviewed on May 10, 2026

See all 2,440 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.