Round-trip from | $214 |
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One-way from | $99 |
Monday is generally a great day to depart. Flying on this day could help you save up to 35%.
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 120% 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 $270. For sooner than that we have options available in the next 3 days from $373.
The best pricing can be found in the month of February. Prices to New Windsor from Chicago average $225. You can even find prices in February for less than $225, 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 23%.
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
$294 - $586
Route
Depart
Return
Price
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Fri 6/28
1 stop9h 47m
New Windsor Stewart
Fri 7/5
1 stop7h 13m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 7/18
1 stop7h 59m
New Windsor Stewart
Mon 7/22
1 stop7h 15m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 7/25
1 stop7h 59m
New Windsor Stewart
Mon 7/29
1 stop7h 15m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 7/6
1 stop9h 09m
New Windsor Stewart
Fri 7/12
1 stop7h 15m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 7/6
1 stop9h 09m
New Windsor Stewart
Fri 7/12
2 stops22h 15m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Thu 7/25
2 stops9h 57m
New Windsor Stewart
Mon 7/29
1 stop7h 15m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 7/6
1 stop9h 09m
New Windsor Stewart
Fri 7/12
3 stops33h 40m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sat 7/6
2 stops18h 38m
New Windsor Stewart
Fri 7/12
3 stops33h 40m
Chicago O'Hare IntlNew Windsor Stewart
ORD - SWF
ORDSWF
Chicago O'Hare Intl
Sun 10/6
1 stop9h 32m
New Windsor Stewart
Sun 10/13
2 stops13h 39m
No data available for this route at this time. Please check back soon.
NYC Temperature | 33.8 - 77 °F |
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Crew
Entertainment
Food
Comfort
Boarding
Overall
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
Crew
Entertainment
Food
Comfort
Boarding
Overall
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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