When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 56 days in advance, which can save you up to 96% on flights from New Windsor to Illinois compared to booking the week you need them. Waiting 56 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 $281. For sooner than that we have options available in the next 3 days from $423.
The best pricing can be found in the month of January. Prices to Illinois from New Windsor average $258. You can even find prices in January for less than $258, as users have found deals to Illinois from as low as $86. The month of June appears to be one of the more expensive times to travel to Illinois from New Windsor. Flying in the targeted month can save you up to 24%.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Windsor to Illinois as you normally would.
Fly from
Fly to
Budget
$344 - $430
Route
Depart
Return
Price
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 7/26
1 stop7h 15m
Chicago O'Hare Intl
Sun 7/28
1 stop7h 59m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 7/19
1 stop7h 15m
Chicago O'Hare Intl
Sun 7/21
1 stop7h 59m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 7/26
1 stop7h 15m
Chicago O'Hare Intl
Sun 7/28
2 stops8h 47m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 7/12
1 stop7h 15m
Chicago O'Hare Intl
Sun 7/14
1 stop7h 59m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Sun 6/16
1 stop9h 40m
Chicago O'Hare Intl
Wed 6/19
2 stops15h 00m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 7/5
1 stop7h 13m
Chicago O'Hare Intl
Sun 7/7
1 stop7h 59m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 7/5
1 stop7h 13m
Chicago O'Hare Intl
Sun 7/7
1 stop7h 59m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 7/19
1 stop7h 15m
Chicago O'Hare Intl
Sun 7/21
2 stops8h 47m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 7/12
1 stop7h 15m
Chicago O'Hare Intl
Sun 7/14
2 stops8h 47m
No data available for this route at this time. Please check back soon.
Food
Boarding
Comfort
Overall
Crew
Entertainment
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
Food
Boarding
Comfort
Overall
Crew
Entertainment
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