Fly from
Fly to
Route
Depart
Return
Price
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 12/11
8:20 am-6:50 pm
1 stop9h 30m
New Windsor Stewart
Fri 12/13
12:55 pm-9:07 pm
1 stop9h 12m
MinneapolisNew Windsor
MSP - SWF
MSPSWF
Minneapolis St Paul
Sun 12/8
1:02 pm-12:05 pm
2 stops22h 03m
New Windsor Stewart
Sun 12/15
6:30 pm-11:57 am
2 stops18h 27m
MilwaukeeNew Windsor
MKE - SWF
MKESWF
Milwaukee-Mitchell
Mon 12/30
5:00 am-5:37 pm
1 stop11h 37m
New Windsor Stewart
Sat 1/4
7:30 pm-9:39 am
1 stop15h 09m
ChicagoNew Windsor
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 12/11
8:20 am-6:50 pm
1 stop9h 30m
MilwaukeeNew Windsor
MKE - SWF
MKESWF
Milwaukee-Mitchell
Mon 12/23
5:00 am-5:37 pm
1 stop11h 37m
MinneapolisNew Windsor
MSP - SWF
MSPSWF
Minneapolis St Paul
Mon 2/10
5:54 am-6:50 pm
1 stop11h 56m
MadisonNew Windsor
MSN - SWF
MSNSWF
Madison Truax Field
Wed 12/18
6:05 pm-5:49 pm
3 stops22h 44m
Currently, October is the cheapest month in which you can book a flight from Wisconsin to New Windsor (average of $109). Flying from Wisconsin to New Windsor in December is currently the most expensive (average of $197). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.