When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 57 days in advance, which can save you up to 67% on flights from Wisconsin to New Windsor compared to booking the week you need them. Waiting 57 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $191. For sooner than that we have options available in the next 3 days from $353.
Our data shows that January tends to be the cheapest month to fly to New Windsor from Wisconsin. Users have commonly found prices around $206 for the month, but tickets can be as low as $77. Due to multiple factors, prepare for potentially higher prices in November.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Wisconsin to New Windsor as you normally would.
Fly from
Fly to
Budget
$341 - $385
Route
Depart
Return
Price
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 6/6
3 stops26h 39m
New Windsor Stewart
Sun 6/9
2 stops24h 36m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 5/31
1 stop9h 23m
New Windsor Stewart
Sun 6/2
1 stop12h 47m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 6/6
3 stops29h 46m
New Windsor Stewart
Sun 6/9
3 stops32h 47m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 6/6
2 stops15h 02m
New Windsor Stewart
Sun 6/9
2 stops24h 36m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 5/31
1 stop9h 23m
New Windsor Stewart
Sun 6/2
1 stop12h 47m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 6/7
1 stop9h 47m
New Windsor Stewart
Sun 6/9
2 stops24h 36m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 5/31
1 stop9h 23m
New Windsor Stewart
Sun 6/2
2 stops25h 43m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 5/31
1 stop9h 23m
New Windsor Stewart
Sun 6/2
3 stops25h 43m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 6/7
1 stop9h 47m
New Windsor Stewart
Sun 6/9
3 stops32h 47m
No data available for this route at this time. Please check back soon.
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