When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 48 days in advance, which can save you up to 76% on flights from New Windsor to Illinois compared to booking the week you need them. Waiting 48 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 $302. For sooner than that we have options available in the next 3 days from $415.
The best pricing can be found in the month of February. Prices to Illinois from New Windsor average $268. You can even find prices in February for less than $268, as users have found deals to Illinois from as low as $107. 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 34%.
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
$325 - $443
Route
Depart
Return
Price
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/30
1 stop12h 47m
Chicago O'Hare Intl
Sun 6/2
2 stops24h 08m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 6/6
1 stop11h 16m
Chicago O'Hare Intl
Sun 6/9
2 stops17h 48m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 5/17
1 stop8h 42m
Chicago O'Hare Intl
Sun 5/19
2 stops24h 08m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/30
2 stops25h 43m
Chicago O'Hare Intl
Sun 6/2
2 stops24h 08m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 6/6
2 stops26h 58m
Chicago O'Hare Intl
Sun 6/9
2 stops24h 04m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/30
3 stops25h 43m
Chicago O'Hare Intl
Sun 6/2
2 stops24h 08m
New Windsor StewartLambert-St Louis
SWF - STL
SWFSTL
New Windsor Stewart
Sun 5/12
1 stop9h 15m
Lambert-St Louis
Sat 5/18
2 stops15h 30m
New Windsor StewartLambert-St Louis
SWF - STL
SWFSTL
New Windsor Stewart
Sun 5/12
1 stop9h 15m
Lambert-St Louis
Sat 5/18
1 stop21h 06m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Thu 5/30
3 stops25h 43m
Chicago O'Hare Intl
Sun 6/2
3 stops29h 21m
No data available for this route at this time. Please check back soon.
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