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 according to our data. United Airlines is the first choice among our users, with 37% 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.

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.

$89 Cheap Flights from Chicago to New Windsor in 2025/26

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0 bags

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Cheap round-trip flights

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8:43 pm - 10:19 am

ORD

SWF

12h 36m1 stop

12:13 pm - 7:41 pm

SWF

ORD

8h 28m1 stop

$211Multiple Airlines

Thu, Jan 15 - Thu, Jan 22

8:51 pm - 6:43 pm

ORD

SWF

20h 52m1 stop

12:13 pm - 10:35 am

SWF

ORD

23h 22m1 stop

$237Multiple Airlines

Sun, Jan 18 - Thu, Jan 22

5:15 am - 10:19 am

ORD

SWF

28h 04m1 stop

12:13 pm - 11:46 pm

SWF

ORD

12h 33m2 stops

$241Multiple Airlines

Thu, Jan 15 - Thu, Jan 22

8:51 pm - 6:43 pm

ORD

SWF

20h 52m1 stop

12:13 pm - 11:46 pm

SWF

ORD

12h 33m2 stops

$267Multiple Airlines

Sun, Jan 18 - Thu, Jan 22

6:12 am - 11:03 am

MDW

SWF

27h 51m2 stops

12:13 pm - 7:52 pm

SWF

MDW

8h 39m1 stop

$358Multiple Airlines

Wed, Dec 31 - Sun, Feb 1

3:10 pm - 11:03 am

MDW

SWF

18h 53m1 stop

12:13 pm - 7:52 pm

SWF

MDW

8h 39m1 stop

$360Multiple Airlines

Wed, Dec 31 - Sun, Feb 1

7:41 pm - 11:39 am

ORD

SWF

14h 58m1 stop

10:29 am - 11:41 pm

SWF

ORD

14h 12m1 stop

$416Multiple Airlines

Sat, Mar 14 - Sun, Mar 22

8:43 pm - 10:19 am

ORD

SWF

12h 36m1 stop

11:42 am - 9:13 pm

SWF

ORD

10h 31m1 stop

$431Multiple Airlines

Sun, Feb 8 - Sun, Feb 15

7:41 pm - 9:39 am

ORD

SWF

12h 58m1 stop

10:29 am - 11:41 pm

SWF

ORD

14h 12m1 stop

$499Multiple Airlines

Wed, Mar 18 - Sun, Mar 22

8:09 pm - 11:44 am

ORD

SWF

14h 35m2 stops

12:13 pm - 7:41 pm

SWF

ORD

8h 28m1 stop

$533Multiple Airlines

Sun, Jan 4 - Thu, Jan 8

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Thu 1/22

12:13 pm-7:41 pm

1 stop8h 28m

$211

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/18

8:51 pm-6:43 pm

1 stop20h 52m

New Windsor Stewart

Thu 1/22

12:13 pm-10:35 am

1 stop23h 22m

$237

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

5:15 am-10:19 am

1 stop28h 04m

New Windsor Stewart

Thu 1/22

12:13 pm-11:46 pm

2 stops12h 33m

$241

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/18

8:51 pm-6:43 pm

1 stop20h 52m

New Windsor Stewart

Thu 1/22

12:13 pm-11:46 pm

2 stops12h 33m

$267

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 12/31

6:12 am-11:03 am

2 stops27h 51m

New Windsor Stewart

Sun 2/1

12:13 pm-7:52 pm

1 stop8h 39m

$358

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 12/31

3:10 pm-11:03 am

1 stop18h 53m

New Windsor Stewart

Sun 2/1

12:13 pm-7:52 pm

1 stop8h 39m

$360

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/14

7:41 pm-11:39 am

1 stop14h 58m

New Windsor Stewart

Sun 3/22

10:29 am-11:41 pm

1 stop14h 12m

$416

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 2/8

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Sun 2/15

11:42 am-9:13 pm

1 stop10h 31m

$431

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 3/18

7:41 pm-9:39 am

1 stop12h 58m

New Windsor Stewart

Sun 3/22

10:29 am-11:41 pm

1 stop14h 12m

$499

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/4

8:09 pm-11:44 am

2 stops14h 35m

New Windsor Stewart

Thu 1/8

12:13 pm-7:41 pm

1 stop8h 28m

$533

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

Fastest flight time	12h 36m
Direct flights	None

The fastest flight from Chicago to New Windsor takes 12h 36m

There are no direct flights from Chicago to New Windsor. There are no popular flight routes from Chicago to New Windsor.

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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 12h 36m 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 use momondo?

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.