Round-trip from | $214 |
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One-way from | $138 |
Thursday is generally a great day to depart. Flying on this day could help you save up to 238%.
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 54 days in advance, which can save you up to 109% on flights from Chicago to New Windsor compared to booking the week you need them. Waiting 54 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 $266. For sooner than that we have options available in the next 3 days from $381.
The best pricing can be found in the month of January. Prices to New Windsor from Chicago average $235. You can even find prices in January for less than $235, as users have found deals to New Windsor from as low as $108. The month of June appears to be one of the more expensive times to travel to New Windsor from Chicago. Flying in the targeted month can save you up to 31%.
Unlike in the morning, when flights are generally more expensive, you can save up to 75% on flights from Chicago to New Windsor by exploring options for tickets at noon.
Fly from
Fly to
Budget
$319 - $484
Route
Depart
Return
Price
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 4/12
1 stop10h 34m
New Windsor Stewart
Sun 4/14
1 stop24h 27m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 4/12
1 stop10h 34m
New Windsor Stewart
Sun 4/14
1 stop24h 27m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 4/10
2 stops22h 12m
New Windsor Stewart
Fri 4/12
2 stops11h 20m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 4/10
3 stops20h 40m
New Windsor Stewart
Fri 4/12
2 stops11h 20m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 4/10
3 stops20h 40m
New Windsor Stewart
Fri 4/12
3 stops30h 57m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 4/12
1 stop12h 50m
New Windsor Stewart
Sun 4/14
3 stops27h 29m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 4/12
1 stop12h 50m
New Windsor Stewart
Sun 4/14
2 stops15h 47m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 4/12
1 stop12h 50m
New Windsor Stewart
Sun 4/14
2 stops15h 47m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Wed 4/10
1 stop15h 00m
New Windsor Stewart
Fri 4/12
2 stops11h 20m
Currently, January is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $125). Flying from Chicago to New Windsor in July is currently the most expensive (average of $186). 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.
January
$125
February
$149
March
$163
April
$149
May
$149
June
$180
July
$186
August
$177
September
$148
October
$159
November
$136
December
$170
NYC Temperature | 33.8 - 77 °F |
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Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Delayed because of crew missing stuck on tarmac at arrival for a full hour this delayed my trip 8 hours this caused me to miss my rental car they were closed for the day when I got there worst flight experience of my life
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Delayed because of crew missing stuck on tarmac at arrival for a full hour this delayed my trip 8 hours this caused me to miss my rental car they were closed for the day when I got there worst flight experience of my life
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