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 98% 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 $278. 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 February. Prices to Illinois from New Windsor average $261. You can even find prices in February for less than $261, as users have found deals to Illinois from as low as $81. 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 33%.
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
$246 - $686
Route
Depart
Return
Price
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Mon 6/3
2 stops35h 43m
Chicago O'Hare Intl
Wed 6/12
2 stops21h 44m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Mon 6/3
1 stop26h 41m
Chicago O'Hare Intl
Wed 6/12
2 stops21h 44m
New Windsor StewartLambert-St Louis
SWF - STL
SWFSTL
New Windsor Stewart
Fri 5/31
3 stops16h 45m
Lambert-St Louis
Sun 6/2
1 stop13h 18m
New Windsor StewartLambert-St Louis
SWF - STL
SWFSTL
New Windsor Stewart
Fri 5/31
3 stops16h 45m
Lambert-St Louis
Sun 6/2
2 stops14h 29m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Mon 6/3
1 stop26h 41m
Chicago O'Hare Intl
Wed 6/12
1 stop14h 29m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 6/21
3 stops38h 29m
Chicago O'Hare Intl
Fri 6/28
1 stop9h 47m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Sat 6/15
1 stop12h 45m
Chicago O'Hare Intl
Sat 6/22
1 stop9h 13m
New Windsor StewartChicago O'Hare Intl
SWF - ORD
SWFORD
New Windsor Stewart
Fri 6/21
3 stops29h 26m
Chicago O'Hare Intl
Fri 6/28
2 stops19h 21m
New Windsor StewartChicago Greater Rockford
SWF - RFD
SWFRFD
New Windsor Stewart
Sun 5/26
1 stop23h 25m
Chicago Greater Rockford
Wed 5/29
1 stop21h 11m
No data available for this route at this time. Please check back soon.
Crew
Boarding
Comfort
Food
Overall
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
Crew
Boarding
Comfort
Food
Overall
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
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