To save up to 100% 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 $236 1-2 weeks out and tickets from $355 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 $211. You can even find prices in February for less than $211, as users have found deals to New Windsor from as low as $73. The month of November 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 18%.
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
$239 - $441
Route
Depart
Return
Price
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 9/26
2 stops20h 49m
New Windsor Stewart
Mon 9/30
2 stops25h 41m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 9/26
1 stop22h 13m
New Windsor Stewart
Mon 9/30
2 stops25h 41m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 10/3
2 stops23h 15m
New Windsor Stewart
Mon 10/7
2 stops11h 54m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 10/3
3 stops36h 16m
New Windsor Stewart
Mon 10/7
2 stops11h 54m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 8/7
2 stops17h 03m
New Windsor Stewart
Fri 8/9
1 stop7h 15m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 8/7
3 stops22h 45m
New Windsor Stewart
Fri 8/9
1 stop7h 15m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 8/9
2 stops18h 54m
New Windsor Stewart
Mon 8/12
1 stop7h 15m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 8/7
2 stops17h 03m
New Windsor Stewart
Fri 8/9
3 stops28h 07m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 8/7
3 stops20h 31m
New Windsor Stewart
Fri 8/9
3 stops28h 07m
No data available for this route at this time. Please check back soon.