What airlines fly to New Windsor?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to New Windsor from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to New Windsor. Keep in mind that there are 6 different airlines that fly to New Windsor on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to New Windsor Stewart Airport?

Prices for flights from Chicago O'Hare Intl Airport to New Windsor Stewart Airport are refreshed on a daily basis.

How old do you have to be to fly from Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport to New Windsor Stewart Airport.

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

The travel and health documents required for your trip to New Windsor Stewart Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at New Windsor Stewart Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$104 Cheap Flights from Chicago O'Hare Intl Airport to New Windsor in 2025/26

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0 bags

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Find the cheapest flights from Chicago O'Hare Intl Airport to New York

Round-trip

One-way

Last minute

Cheap round-trip flights

7:49 pm - 6:40 pmORD-SWF

21h 51m1 stop

12:27 pm - 9:00 pmSWF-ORD

9h 33m1 stop

$213Multiple Airlines

Find Deal

Thu, Dec 11 - Mon, Dec 15

5:59 pm - 10:41 amORD-SWF

15h 42m1 stop

12:01 pm - 9:00 pmSWF-ORD

9h 59m1 stop

$214Multiple Airlines

Find Deal

Thu, Nov 6 - Mon, Nov 10

6:44 pm - 11:21 amORD-SWF

15h 37m1 stop

11:01 am - 11:45 pmSWF-ORD

13h 44m1 stop

$219Multiple Airlines

Find Deal

Thu, Oct 2 - Mon, Oct 6

6:44 pm - 11:21 amORD-SWF

15h 37m1 stop

11:01 am - 11:45 pmSWF-ORD

13h 44m1 stop

$220Multiple Airlines

Find Deal

Thu, Oct 2 - Mon, Oct 6

10:05 pm - 6:40 pmORD-SWF

19h 35m2 stops

12:27 pm - 9:00 pmSWF-ORD

9h 33m1 stop

$250Multiple Airlines

Find Deal

Thu, Dec 11 - Mon, Dec 15

10:18 am - 11:03 amORD-SWF

23h 45m1 stop

6:28 pm - 9:00 pmSWF-ORD

27h 32m2 stops

$362Multiple Airlines

Find Deal

Wed, Dec 10 - Thu, Dec 11

5:17 pm - 11:03 amORD-SWF

16h 46m1 stop

11:43 am - 9:33 pmSWF-ORD

10h 50m1 stop

$399Multiple Airlines

Find Deal

Wed, Oct 1 - Sun, Oct 5

11:57 am - 4:55 pmORD-SWF

27h 58m2 stops

11:43 am - 9:33 pmSWF-ORD

10h 50m1 stop

$431Multiple Airlines

Find Deal

Wed, Oct 1 - Sun, Oct 5

7:43 pm - 11:03 amORD-SWF

14h 20m1 stop

12:24 pm - 9:33 pmSWF-ORD

10h 09m2 stops

$520Multiple Airlines

Find Deal

Sat, Oct 25 - Mon, Oct 27

7:43 pm - 11:03 amORD-SWF

14h 20m1 stop

12:24 pm - 9:33 pmSWF-ORD

10h 09m2 stops

$556Multiple Airlines

Find Deal

Sat, Oct 11 - Fri, Oct 17

momondo Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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

Thu 12/11

7:49 pm-6:40 pm

1 stop21h 51m

New Windsor Stewart

Mon 12/15

12:27 pm-9:00 pm

1 stop9h 33m

$213

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/6

5:59 pm-10:41 am

1 stop15h 42m

New Windsor Stewart

Mon 11/10

12:01 pm-9:00 pm

1 stop9h 59m

$214

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/2

6:44 pm-11:21 am

1 stop15h 37m

New Windsor Stewart

Mon 10/6

11:01 am-11:45 pm

1 stop13h 44m

$219

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/2

6:44 pm-11:21 am

1 stop15h 37m

New Windsor Stewart

Mon 10/6

11:01 am-11:45 pm

1 stop13h 44m

$220

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/11

10:05 pm-6:40 pm

2 stops19h 35m

New Windsor Stewart

Mon 12/15

12:27 pm-9:00 pm

1 stop9h 33m

$250

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/10

10:18 am-11:03 am

1 stop23h 45m

New Windsor Stewart

Thu 12/11

6:28 pm-9:00 pm

2 stops27h 32m

$362

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 10/1

5:17 pm-11:03 am

1 stop16h 46m

New Windsor Stewart

Sun 10/5

11:43 am-9:33 pm

1 stop10h 50m

$399

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 10/1

11:57 am-4:55 pm

2 stops27h 58m

New Windsor Stewart

Sun 10/5

11:43 am-9:33 pm

1 stop10h 50m

$431

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 10/25

7:43 pm-11:03 am

1 stop14h 20m

New Windsor Stewart

Mon 10/27

12:24 pm-9:33 pm

2 stops10h 09m

$520

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 10/11

7:43 pm-11:03 am

1 stop14h 20m

New Windsor Stewart

Fri 10/17

12:24 pm-9:33 pm

2 stops10h 09m

$556

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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

Prices

Airlines

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 Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport 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.

When to book flights from Chicago O'Hare Intl Airport to New Windsor

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to New Windsor according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to New Windsor (ORD to SWF) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to New Windsor

Direct flights	None

There are no direct flights from Chicago O'Hare Intl Airport to New Windsor. There are no popular flight routes from Chicago O'Hare Intl Airport to New Windsor.

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How far is Chicago O'Hare Intl to New Windsor Stewart by plane?
The straight-line distance from Chicago O'Hare Intl to New Windsor Stewart is 715.3 mi. Flights usually cover this in 13h 38m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to New Windsor Stewart Airport?
Prices for flights from Chicago O'Hare Intl Airport to New Windsor Stewart Airport are refreshed on a daily basis.
How old do you have to be to fly from Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport to New Windsor Stewart Airport.
What documentation or ID do you need to fly to New Windsor Stewart Airport?
The travel and health documents required for your trip to New Windsor Stewart Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at New Windsor Stewart Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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Why use momondo?

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

Finding the right flight to New Windsor from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to New Windsor quick and easy, saving you time and money.

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

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

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to New Windsor.

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

Yes. momondo can track prices for Chicago 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.