To save up to 123% on this flight, we recommend booking at least 54 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago O'Hare Intl Airport to New Windsor from $276 1-2 weeks out and tickets from $368 for flights departing within the next 72 hours.
The best pricing can be found in the month of February. Prices to New Windsor from Chicago O'Hare Intl Airport average $228. You can even find prices in February for less than $228, as users have found deals to New Windsor from as low as $74. The month of June appears to be one of the more expensive times to travel to New Windsor from Chicago O'Hare Intl Airport. Flying in the targeted month can save you up to 30%.
When flying from Chicago O'Hare Intl Airport to New Windsor, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$432 - $562
Route
Depart
Return
Price
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 6/1
2 stops14h 05m
New Windsor Stewart
Sun 6/30
2 stops26h 58m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 6/1
1 stop13h 38m
New Windsor Stewart
Sun 6/30
2 stops26h 58m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 5/24
1 stop12h 30m
New Windsor Stewart
Mon 5/27
2 stops21h 05m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 6/1
2 stops14h 05m
New Windsor Stewart
Sun 6/30
3 stops34h 18m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 5/24
1 stop12h 30m
New Windsor Stewart
Mon 5/27
1 stop7h 08m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 6/1
3 stops25h 15m
New Windsor Stewart
Sun 6/30
3 stops34h 18m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 6/1
1 stop13h 38m
New Windsor Stewart
Sun 6/30
1 stop13h 56m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 5/16
3 stops28h 06m
New Windsor Stewart
Sun 5/19
2 stops25h 43m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 5/16
3 stops28h 06m
New Windsor Stewart
Sun 5/19
3 stops25h 43m
No data available for this route at this time. Please check back soon.
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