What airlines fly to New Windsor?

United Airlines, American 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. United Airlines is the first choice among our users, with 35% 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.

$84 Cheap Flights from Chicago O'Hare Intl Airport to New Windsor in 2025/26

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:44 am - 11:37 amORD-SWF

22h 53m2 stops

11:43 am - 1:16 pmSWF-ORD

26h 33m1 stop

$220Multiple Airlines

Find Deal

Thu, Dec 4 - Thu, Dec 11

2:26 pm - 11:03 amORD-SWF

19h 37m1 stop

11:43 am - 1:16 pmSWF-ORD

26h 33m1 stop

$230Multiple Airlines

Find Deal

Sat, Dec 6 - Thu, Dec 11

2:26 pm - 11:03 amORD-SWF

19h 37m1 stop

12:27 pm - 11:08 amSWF-ORD

23h 41m1 stop

$232Multiple Airlines

Find Deal

Sat, Dec 6 - Mon, Dec 8

8:00 am - 11:03 amORD-SWF

26h 03m2 stops

12:27 pm - 8:01 pmSWF-ORD

8h 34m1 stop

$239Multiple Airlines

Find Deal

Wed, Dec 3 - Fri, Dec 5

8:00 am - 11:03 amORD-SWF

26h 03m2 stops

11:43 am - 1:16 pmSWF-ORD

26h 33m1 stop

$242Multiple Airlines

Find Deal

Wed, Dec 3 - Thu, Dec 11

4:21 pm - 11:37 amORD-SWF

18h 16m1 stop

11:43 am - 1:16 pmSWF-ORD

26h 33m1 stop

$244Multiple Airlines

Find Deal

Thu, Dec 4 - Thu, Dec 11

8:00 am - 11:03 amORD-SWF

26h 03m2 stops

12:27 pm - 11:08 amSWF-ORD

23h 41m1 stop

$245Multiple Airlines

Find Deal

Wed, Dec 3 - Mon, Dec 8

4:21 pm - 11:37 amORD-SWF

18h 16m1 stop

12:27 pm - 11:08 amSWF-ORD

23h 41m1 stop

$246Multiple Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

6:48 am - 11:03 amORD-SWF

27h 15m1 stop

12:27 pm - 8:01 pmSWF-ORD

8h 34m1 stop

$250Multiple Airlines

Find Deal

Wed, Dec 3 - Fri, Dec 5

6:48 am - 11:03 amORD-SWF

27h 15m1 stop

11:43 am - 1:16 pmSWF-ORD

26h 33m1 stop

$254Multiple Airlines

Find Deal

Wed, Dec 3 - Thu, Dec 11

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 12/4

11:44 am-11:37 am

2 stops22h 53m

New Windsor Stewart

Thu 12/11

11:43 am-1:16 pm

1 stop26h 33m

$220

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 12/6

2:26 pm-11:03 am

1 stop19h 37m

New Windsor Stewart

Thu 12/11

11:43 am-1:16 pm

1 stop26h 33m

$230

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 12/6

2:26 pm-11:03 am

1 stop19h 37m

New Windsor Stewart

Mon 12/8

12:27 pm-11:08 am

1 stop23h 41m

$232

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/3

8:00 am-11:03 am

2 stops26h 03m

New Windsor Stewart

Fri 12/5

12:27 pm-8:01 pm

1 stop8h 34m

$239

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/3

8:00 am-11:03 am

2 stops26h 03m

New Windsor Stewart

Thu 12/11

11:43 am-1:16 pm

1 stop26h 33m

$242

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/4

4:21 pm-11:37 am

1 stop18h 16m

New Windsor Stewart

Thu 12/11

11:43 am-1:16 pm

1 stop26h 33m

$244

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/3

8:00 am-11:03 am

2 stops26h 03m

New Windsor Stewart

Mon 12/8

12:27 pm-11:08 am

1 stop23h 41m

$245

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/4

4:21 pm-11:37 am

1 stop18h 16m

New Windsor Stewart

Mon 12/8

12:27 pm-11:08 am

1 stop23h 41m

$246

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/3

6:48 am-11:03 am

1 stop27h 15m

New Windsor Stewart

Fri 12/5

12:27 pm-8:01 pm

1 stop8h 34m

$250

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/3

6:48 am-11:03 am

1 stop27h 15m

New Windsor Stewart

Thu 12/11

11:43 am-1:16 pm

1 stop26h 33m

$254

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.

Search flight deals

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 9h 36m, 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.

Newburgh

Kingston

Woodstock

Saugerties

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.