Whitefish Bay Vacation Packages 2026 from $581

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The Latest Whitefish Bay Vacation Packages

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

Oct 23 - Oct 25
The Iron Horse Hotel + Flight
Fifth Ward
2 nights
4.0 star property
9.2/10 - Wonderful (1,271 reviews)
"The outdoor bar is glorious! Comfy beds, nice staff!"
Reviewed August 5, 2026
Roundtrip • Boston (BOS) - Milwaukee (MKE)
BOS - MKE • Nonstop MKE - BOS • 1 stop
~~$723~~
$606
per traveler
found 1 day ago
The Iron Horse Hotel
Sep 25 - Sep 28
Saint Kate - The Arts Hotel + Flight
Downtown Milwaukee
3 nights
4.0 star property
9.8/10 - Exceptional (2,659 reviews)
Roundtrip • Atlanta (ATL) - Milwaukee (MKE)
ATL - MKE • Nonstop MKE - ATL • Nonstop
Save 100% on your flight
~~$1,466~~
$1,045
per traveler
found 7 hours ago
Saint Kate - The Arts Hotel
Oct 28 - Nov 1
The Pfister Hotel + Flight
Downtown Milwaukee
4 nights
4.5 star property
9.6/10 - Exceptional (2,204 reviews)
Roundtrip • Atlanta (ATL) - Milwaukee (MKE)
ATL - MKE • Nonstop MKE - ATL • Nonstop
~~$1,078~~
$790
per traveler
found 17 hours ago
The Pfister Hotel
Oct 16 - Oct 19
Kinn Guesthouse Downtown + Flight
Downtown Milwaukee
2 nights
4.5 star property
9.4/10 - Exceptional (391 reviews)
"Great place, first impression I wasn’t sure if I was in the right place since it was booked for me. Beautiful building, built in the 1800s. Rooms are amazing. Since it is in downtown Milwaukee, it does get a little loud but it’s to be expected. We’ll definitely stay here again."
Reviewed July 30, 2026
Roundtrip • Los Angeles (LAX) - Milwaukee (MKE)
LAX - MKE • 1 stop MKE - LAX • 1 stop
~~$877~~
$731
per traveler
found 1 hour ago
Kinn Guesthouse Downtown
Oct 28 - Nov 1
Landing Apartments at Mayfair Collection + Flight
Wauwatosa
4 nights
4.0 star property
10/10 - Exceptional (4 reviews)
"Instructions to find the Serenity apartments at Wauwatosa Wisconsin weren't great but once we found the actual apartment, it exceeded our expectations. It was truly a home away from home, as it was immaculately clean and had everything needed for a fuss free stay. Shops and restaurants witin walking distance. We highly recommend staying here and will definitely be returning for a longer extended stay!"
Reviewed May 21, 2026
Roundtrip • Atlanta (ATL) - Milwaukee (MKE)
ATL - MKE • Nonstop MKE - ATL • Nonstop
~~$944~~
$805
per traveler
found 4 hours ago
Landing Apartments at Mayfair Collection