To save up to 78% on this flight, we recommend booking at least 57 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Milwaukee to New Windsor from $191 1-2 weeks out and tickets from $346 for flights departing within the next 72 hours.
Due to multiple factors, expect to potentially pay more when booking in November. For low rates, January can be a great choice for travel to New Windsor. Flights to New Windsor from Milwaukee in January are about $208 on average during January, but can be found for as low as $77.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Milwaukee to New Windsor as you normally would.
Fly from
Fly to
Budget
$404 - $497
Route
Depart
Return
Price
Milwaukee-MitchellNew Windsor Stewart
MKE - SWF
MKESWF
Milwaukee-Mitchell
Thu 7/4
2 stops10h 17m
New Windsor Stewart
Thu 7/11
2 stops26h 38m
Milwaukee-MitchellNew Windsor Stewart
MKE - SWF
MKESWF
Milwaukee-Mitchell
Thu 7/4
2 stops10h 17m
New Windsor Stewart
Thu 7/11
1 stop14h 32m
Milwaukee-MitchellNew Windsor Stewart
MKE - SWF
MKESWF
Milwaukee-Mitchell
Thu 7/4
2 stops10h 17m
New Windsor Stewart
Thu 7/11
3 stops32h 15m