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 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 7 different airlines that fly to New Windsor on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to New Windsor Stewart?

Allegiant Air is the most popular carrier operating from Chicago to New Windsor Stewart

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

Prices for flights from Chicago to New Windsor Stewart Airport were last updated today.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago 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.

$97 Cheap Flights from Chicago to New Windsor (CHI-SWF) in 2025

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Find the cheapest flights from Chicago to New York (CHI-SWF)

Round-trip

One-way

Last minute

Cheap round-trip flights

7:29 pm - 10:41 amORD-SWF

14h 12m1 stop

12:01 pm - 1:03 amSWF-ORD

14h 02m1 stop

$244

Find Deal

Thu, Oct 30 - Mon, Nov 3

10:12 am - 6:00 pmORD-SWF

6h 48m1 stop

2:04 pm - 9:58 pmSWF-ORD

8h 54m2 stops

$349

Find Deal

Sun, Aug 31 - Thu, Sep 4

10:12 am - 6:00 pmORD-SWF

6h 48m1 stop

2:04 pm - 10:52 amSWF-ORD

21h 48m3 stops

$411

Find Deal

Sun, Aug 31 - Thu, Sep 4

7:29 pm - 11:03 amORD-SWF

38h 34m2 stops

11:01 am - 11:45 pmSWF-ORD

13h 44m1 stop

$441

Find Deal

Fri, Oct 10 - Mon, Oct 13

8:49 pm - 11:44 amORD-SWF

13h 55m2 stops

11:43 am - 7:44 pmSWF-ORD

9h 01m1 stop

$451

Find Deal

Sun, Sep 14 - Thu, Sep 18

10:12 am - 1:05 pmORD-SWF

25h 53m3 stops

2:04 pm - 9:58 pmSWF-ORD

8h 54m2 stops

$465

Find Deal

Sun, Aug 31 - Thu, Sep 4

7:43 pm - 11:03 amORD-SWF

14h 20m1 stop

11:43 am - 9:33 pmSWF-ORD

10h 50m1 stop

$502

Find Deal

Sat, Oct 18 - Sun, Oct 26

8:49 pm - 11:44 amORD-SWF

13h 55m2 stops

11:43 am - 9:33 pmSWF-ORD

10h 50m1 stop

$518

Find Deal

Sun, Oct 5 - Sun, Oct 12

10:12 am - 1:05 pmORD-SWF

25h 53m3 stops

2:04 pm - 10:52 amSWF-ORD

21h 48m3 stops

$527

Find Deal

Sun, Aug 31 - Thu, Sep 4

10:12 am - 6:00 pmORD-SWF

6h 48m1 stop

12:17 pm - 11:59 pmSWF-ORD

12h 42m2 stops

$543

Find Deal

Thu, Aug 28 - Mon, Sep 1

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/30

7:29 pm-10:41 am

1 stop14h 12m

New Windsor Stewart

Mon 11/3

12:01 pm-1:03 am

1 stop14h 02m

$244

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 8/31

10:12 am-6:00 pm

1 stop6h 48m

New Windsor Stewart

Thu 9/4

2:04 pm-9:58 pm

2 stops8h 54m

$349

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 8/31

10:12 am-6:00 pm

1 stop6h 48m

New Windsor Stewart

Thu 9/4

2:04 pm-10:52 am

3 stops21h 48m

$411

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 10/10

7:29 pm-11:03 am

2 stops38h 34m

New Windsor Stewart

Mon 10/13

11:01 am-11:45 pm

1 stop13h 44m

$441

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 9/14

8:49 pm-11:44 am

2 stops13h 55m

New Windsor Stewart

Thu 9/18

11:43 am-7:44 pm

1 stop9h 01m

$451

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 8/31

10:12 am-1:05 pm

3 stops25h 53m

New Windsor Stewart

Thu 9/4

2:04 pm-9:58 pm

2 stops8h 54m

$465

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 10/18

7:43 pm-11:03 am

1 stop14h 20m

New Windsor Stewart

Sun 10/26

11:43 am-9:33 pm

1 stop10h 50m

$502

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 10/5

8:49 pm-11:44 am

2 stops13h 55m

New Windsor Stewart

Sun 10/12

11:43 am-9:33 pm

1 stop10h 50m

$518

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 8/31

10:12 am-1:05 pm

3 stops25h 53m

New Windsor Stewart

Thu 9/4

2:04 pm-10:52 am

3 stops21h 48m

$527

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 8/28

10:12 am-6:00 pm

1 stop6h 48m

New Windsor Stewart

Mon 9/1

12:17 pm-11:59 pm

2 stops12h 42m

$543

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 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 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 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 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 to New Windsor

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

Estimated round-trip price

Cheap Chicago to New Windsor (CHI to SWF) flight deals and tips

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

Best Price Found	$99
Fastest flight time	6h 48m
Direct flights	None
Airports in New Windsor	1 airport

The best one-way flight to New Windsor from Chicago in the past 72 hours is $99. The best round-trip flight deal from Chicago to New Windsor found on momondo in the last 72 hours is $244.

The fastest flight from Chicago to New Windsor takes 6h 48m

There are no direct flights from Chicago to New Windsor. Popular non-direct routes for this connection are Chicago O'Hare Intl Airport - New Windsor Stewart Airport and Chicago Midway Airport - New Windsor Stewart Airport.

There is 1 airport near New Windsor: New Windsor Stewart (SWF)

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How far is Chicago to New Windsor Stewart by plane?
There are 701.4 mi between Chicago and New Windsor Stewart. Typically, this will take 6h 48m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to New Windsor Stewart Airport?
Prices for flights from Chicago to New Windsor Stewart Airport were last updated today.
How old do you have to be to fly from Chicago to New Windsor Stewart Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago 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 should I use momondo to find a flight deal from Chicago to New Windsor?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to New Windsor for you.

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

All flight searches from Chicago to New Windsor on momondo can be filtered to show those which offer flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to New Windsor from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to New Windsor from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.