Southern Wisconsin Vacation Packages 2026 from $664

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A rocky cliff with a clear sky and a body of water.

The Latest Southern Wisconsin Vacation Packages

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

Oct 2 - Oct 5
The Iron Horse Hotel + Flight
Fifth Ward
3 nights
4.0 star property
9.2/10 - Wonderful (1,252 reviews)
"Clean , spacious room. Fun lobby with cool original rock & roll art. (With an artist creating new art in the lobby.) great outdoor patio, The Yard, to enjoy Wisconsin’’a finest cheese curds and a Spotted Cow on tap."
Reviewed July 30, 2026
Roundtrip • Dallas (DFW) - Milwaukee (MKE)
DFW - MKE • Nonstop MKE - DAL • Nonstop
~~$860~~
$664
per traveler
found 1 day ago
The Iron Horse Hotel
Oct 9 - Oct 12
The Pfister Hotel + Flight
Downtown Milwaukee
3 nights
4.5 star property
9.6/10 - Exceptional (2,179 reviews)
"This is a beautiful historic hotel and will always be a jewel in Milwaukee. The rooms were well appointed common areas were beautiful. I especially liked the café in the hotel. The food is excellent and the staff could not be more gracious. I do not believe the people working at the reception area are customer service oriented enough for this beautiful and historic hotel."
Reviewed July 29, 2026
Roundtrip • Dallas (DFW) - Milwaukee (MKE)
DAL - MKE • Nonstop MKE - DFW • 1 stop
Save 100% on your flight
~~$1,655~~
$988
per traveler
found 4 hours ago
The Pfister Hotel
Sep 30 - Oct 4
Graduate by Hilton Madison + Flight
Downtown Madison
4 nights
4.0 star property
9.0/10 - Wonderful (1,001 reviews)
Roundtrip • Chicago (CHI) - Madison (MSN)
ORD - MSN • Nonstop MSN - ORD • Nonstop
Save 100% on your flight
~~$1,921~~
$1,475
per traveler
found 1 day ago
Graduate by Hilton Madison
Sep 24 - Sep 27
Kinn Guesthouse Downtown + Flight
Downtown Milwaukee
3 nights
4.5 star property
9.4/10 - Exceptional (390 reviews)
"Great location to the Third District. Felt very safe. Had a little issue with our code working the elevator, but it was corrected. Parking was a little confusing at first, but was in a great location and felt very secured. We had a great time and will be back; wouldn't hesitate to stay again. The only other thing it would have been nice to have a refrigerator in the room, since you are so close to the public market."
Reviewed July 29, 2026
Roundtrip • Dallas (DFW) - Milwaukee (MKE)
DFW - MKE • Nonstop MKE - DFW • 1 stop
~~$1,198~~
$970
per traveler
found 9 hours ago
Kinn Guesthouse Downtown
Sep 30 - Oct 4
Fairfield Inn & Suites by Marriott Madison East + Flight
Madison
4 nights
3.0 star property
9.2/10 - Wonderful (1,000 reviews)
Roundtrip • Chicago (CHI) - Madison (MSN)
ORD - MSN • Nonstop MSN - ORD • Nonstop
~~$993~~
$811
per traveler
found 1 day ago
Fairfield Inn & Suites by Marriott Madison East

Discover the most popular places to visit in Southern Wisconsin

A baseball game in a stadium with a person holding a hot dog and a drink.

American Family Field

9.0/10 (2,832 reviews)

Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.