Cheap flights from Illinois to New York from $122

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to New York departing on 8/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

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5:16 pm - 10:12 amORD-SWF
15h 56m1 stop
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5:36 pm - 10:31 amSWF-ORD
17h 55m1 stop
Sun, Aug 24 - Mon, Aug 25
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5:05 am - 6:47 pmORD-SWF
12h 42m1 stop
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7:37 pm - 10:31 amSWF-ORD
15h 54m1 stop
Fri, Aug 15 - Mon, Aug 18
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5:16 pm - 10:13 amORD-SWF
15h 57m1 stop
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7:37 pm - 10:31 amSWF-ORD
15h 54m1 stop
Fri, Aug 15 - Mon, Aug 18
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5:05 am - 4:46 pmORD-SWF
10h 41m1 stop
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5:36 pm - 10:31 amSWF-ORD
17h 55m1 stop
Fri, Aug 22 - Mon, Aug 25
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5:05 am - 6:47 pmORD-SWF
12h 42m1 stop
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7:37 pm - 10:31 amSWF-ORD
15h 54m1 stop
Fri, Aug 15 - Mon, Aug 18
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10:26 am - 6:47 pmORD-SWF
7h 21m1 stop
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7:37 pm - 4:10 pmSWF-ORD
21h 33m2 stops
Fri, Aug 15 - Mon, Aug 18
Allegiant Air Logo
9:32 am - 6:47 pmPIA-SWF
8h 15m1 stop
Allegiant Air Logo
11:02 am - 6:09 pmSWF-PIA
8h 07m1 stop
$276Allegiant Air
Find Deal
Fri, Aug 22 - Mon, Aug 25
Allegiant Air Logo
9:32 am - 6:47 pmPIA-SWF
8h 15m1 stop
Allegiant Air Logo
10:57 am - 6:09 pmSWF-PIA
8h 12m1 stop
$291Allegiant Air
Find Deal
Fri, Aug 22 - Fri, Aug 29
Allegiant Air Logo
2:54 pm - 10:13 amMDW-SWF
18h 19m2 stops
Allegiant Air Logo
8:33 pm - 6:17 pmSWF-MDW
22h 44m2 stops
$393Allegiant Air
Find Deal
Fri, Aug 15 - Sun, Aug 17
Breeze Airways Logo
7:19 pm - 11:56 amEVV-SWF
15h 37m1 stop
Breeze Airways Logo
7:52 pm - 6:39 pmSWF-EVV
23h 47m1 stop
$592Breeze Airways
Find Deal
Mon, Aug 18 - Thu, Aug 28

Allegiant Air flights from Illinois to New Windsor

Our best Allegiant Air deals on Illinois to New Windsor flight tickets
Allegiant Air
Aug 22
PIA9:32 amGreater Peoria
8h 15m
1 stop
SWF6:47 pmNew Windsor Stewart
Aug 25
SWF11:02 amNew Windsor Stewart
8h 07m
1 stop
PIA6:09 pmGreater Peoria
Allegiant Air
Aug 22
PIA9:32 amGreater Peoria
8h 15m
1 stop
SWF6:47 pmNew Windsor Stewart
Aug 29
SWF10:57 amNew Windsor Stewart
8h 12m
1 stop
PIA6:09 pmGreater Peoria
Allegiant Air
Aug 15
MDW2:54 pmChicago Midway
18h 19m
2 stops
SWF10:13 amNew Windsor Stewart
Aug 17
SWF8:33 pmNew Windsor Stewart
22h 44m
2 stops
MDW6:17 pmChicago Midway

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to New Windsor that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Illinois to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 8/24

5:16 pm-10:12 am

1 stop15h 56m

New Windsor Stewart

Mon 8/25

5:36 pm-10:31 am

1 stop17h 55m

$212

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 8/15

5:05 am-6:47 pm

1 stop12h 42m

New Windsor Stewart

Mon 8/18

7:37 pm-10:31 am

1 stop15h 54m

$222

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 8/15

5:16 pm-10:13 am

1 stop15h 57m

New Windsor Stewart

Mon 8/18

7:37 pm-10:31 am

1 stop15h 54m

$228

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 8/22

5:05 am-4:46 pm

1 stop10h 41m

New Windsor Stewart

Mon 8/25

5:36 pm-10:31 am

1 stop17h 55m

$230

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 8/15

5:05 am-6:47 pm

1 stop12h 42m

New Windsor Stewart

Mon 8/18

7:37 pm-10:31 am

1 stop15h 54m

$239

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 8/15

10:26 am-6:47 pm

1 stop7h 21m

New Windsor Stewart

Mon 8/18

7:37 pm-4:10 pm

2 stops21h 33m

$248

PeoriaNew Windsor

PIA - SWF

PIASWF

Greater Peoria

Fri 8/22

9:32 am-6:47 pm

1 stop8h 15m

New Windsor Stewart

Mon 8/25

11:02 am-6:09 pm

1 stop8h 07m

$276

PeoriaNew Windsor

PIA - SWF

PIASWF

Greater Peoria

Fri 8/22

9:32 am-6:47 pm

1 stop8h 15m

New Windsor Stewart

Fri 8/29

10:57 am-6:09 pm

1 stop8h 12m

$291

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 8/15

2:54 pm-10:13 am

2 stops18h 19m

New Windsor Stewart

Sun 8/17

8:33 pm-6:17 pm

2 stops22h 44m

$393

EvansvilleNew Windsor

EVV - SWF

EVVSWF

Evansville Dress Regional

Mon 8/18

7:19 pm-11:56 am

1 stop15h 37m

New Windsor Stewart

Thu 8/28

7:52 pm-6:39 pm

1 stop23h 47m

$592

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to New York from

How to get the cheapest flight ticket from Illinois to New Windsor

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to New Windsor?

On average, the least expensive day to fly to New Windsor from Illinois is on a Thursday. momondo users have found tickets for Thursday departures for as low as $119. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Illinois to New Windsor on a Friday will generally be more expensive and average around $287. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to New Windsor?

According to our data, the cheapest time of day to fly to New Windsor is in the afternoon. momondo users have found flights departing from Illinois to New Windsor in the afternoon for as low as $170. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to New Windsor are more costly in the morning, with an average ticket price of $180. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

Cheap Illinois to New Windsor flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to New Windsor

Best Price Found

$122

Fastest flight time

6h 48m

Direct flights

None

Airports in New Windsor

1 airport
The best one-way flight to New Windsor from Illinois in the past 72 hours is $122. The best round-trip flight deal from Illinois to New Windsor found on momondo in the last 72 hours is $212.
The fastest flight from Illinois to New Windsor takes 6h 48m
There are no direct flights from Illinois to New Windsor. Popular non-direct routes for this connection are Chicago O'Hare Intl Airport - New Windsor Stewart Airport, Chicago Midway Airport - New Windsor Stewart Airport and Lambert-St Louis Airport - New Windsor Stewart Airport.
There is 1 airport near New Windsor: New Windsor Stewart (SWF)

  • When did momondo last update prices for flights from Illinois to New Windsor Stewart Airport?

    Prices for flights from Illinois to New Windsor Stewart Airport are updated daily.

  • How old do you have to be to fly from Illinois to New Windsor Stewart Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to New Windsor Stewart Airport.

  • What documentation or ID do you need to fly to New Windsor Stewart Airport?

    The required travel and health documents for your New Windsor Stewart Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at New Windsor Stewart Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.


Traveling to a place near New York?

Book flights to New York if you plan to visit one of these locations
Newburgh
Kingston
Woodstock
Saugerties

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to New Windsor?

It is quick and easy to find Illinois to New Windsor flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to New Windsor that suits you.

Can I find flights from Illinois to New Windsor with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Illinois to New Windsor flights to just show those with flexible booking policies.

How can momondo help me find flights from Illinois to New Windsor?

Once you have performed a search for Illinois to New Windsor flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Illinois to New Windsor right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Illinois to New Windsor flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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1 adult
Tue 8/5
Tue 8/12

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