Round-trip from | $223 |
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One-way from | $114 |
Users have found that booking a flight from New Windsor to Chicago at least 56 days early can save you up to 98% on average compared to booking a flight this week. If booking 56 days before your flight isn’t an option for you, users have found flights from New Windsor to Chicago for as little as $278 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $423 for flights departing within the next 3 days.
February can be a great time to fly to Chicago from New Windsor with a flight ticket averaging about $261. Cheapflights users have found deals in the month of February for as cheap as $81. The most expensive prices can be found in the month of June.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Windsor to Chicago as you normally would.
Fly from
Fly to
Budget
$424 - $631
Route
Depart
Return
Price
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Sun 6/9
1 stop13h 56m
Chicago O'Hare Intl
Mon 6/10
1 stop9h 47m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Sun 6/9
2 stops11h 22m
Chicago O'Hare Intl
Mon 6/10
1 stop9h 47m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/16
1 stop12h 47m
Chicago O'Hare Intl
Sun 5/19
3 stops24h 08m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/16
2 stops25h 43m
Chicago O'Hare Intl
Sun 5/19
3 stops24h 08m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/16
1 stop12h 47m
Chicago O'Hare Intl
Sun 5/19
2 stops16h 32m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/16
1 stop12h 47m
Chicago O'Hare Intl
Sun 5/19
1 stop16h 40m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/16
3 stops29h 46m
Chicago O'Hare Intl
Sun 5/19
3 stops24h 08m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/16
1 stop12h 47m
Chicago O'Hare Intl
Mon 5/20
2 stops9h 54m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/23
1 stop12h 47m
Chicago O'Hare Intl
Sun 5/26
2 stops22h 40m
No data available for this route at this time. Please check back soon.
Currently, February is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $244). Flying from New Windsor to Chicago in June is currently the most expensive (average of $342). 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
$248
February
$244
March
$280
April
$258
May
$278
June
$342
July
$327
August
$274
September
$258
October
$248
November
$270
December
$248
CHI Temperature | 23 - 73.4 °F |
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Crew
Food
Comfort
Boarding
Entertainment
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
Food
Comfort
Boarding
Entertainment
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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Yes, Cheapflights offers price alerts on Stewart to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.