Round-trip from | $214 |
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One-way from | $131 |
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 123% 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 $276. For sooner than that we have options available in the next 3 days from $368.
The best pricing can be found in the month of February. Prices to New Windsor from Chicago average $227. You can even find prices in February for less than $227, 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. Flying in the targeted month can save you up to 27%.
Unlike in the morning, when flights are generally more expensive, you can save up to 9% on flights from Chicago to New Windsor by exploring options for tickets at noon.
Fly from
Fly to
Budget
$375 - $618
Route
Depart
Return
Price
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Mon 6/10
1 stop9h 47m
New Windsor Stewart
Mon 6/17
2 stops20h 48m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Mon 6/10
1 stop9h 47m
New Windsor Stewart
Mon 6/17
3 stops29h 54m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sun 5/26
2 stops24h 08m
New Windsor Stewart
Sun 6/2
1 stop10h 20m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sun 5/26
2 stops24h 08m
New Windsor Stewart
Sun 6/2
2 stops24h 30m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sun 5/26
2 stops24h 08m
New Windsor Stewart
Sun 6/2
3 stops25h 43m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sun 5/26
3 stops27h 36m
New Windsor Stewart
Sun 6/2
3 stops25h 43m
No data available for this route at this time. Please check back soon.
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 $188). 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
$163
May
$146
June
$173
July
$188
August
$158
September
$148
October
$165
November
$136
December
$170
NYC Temperature | 33.8 - 77 °F |
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Overall
Entertainment
Boarding
Comfort
Crew
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
Overall
Entertainment
Boarding
Comfort
Crew
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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