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 35% 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.

$86 Cheap Flights from Chicago to New Windsor in 2025/26

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0 bags

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4:49 pm - 11:37 amORD-SWF

17h 48m2 stops

12:27 pm - 12:09 amSWF-ORD

12h 42m1 stop

$221Multiple Airlines

Find Deal

Thu, Dec 11 - Mon, Dec 15

4:21 pm - 11:37 amORD-SWF

18h 16m1 stop

12:27 pm - 12:09 amSWF-ORD

12h 42m1 stop

$229Multiple Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

8:22 pm - 10:19 amORD-SWF

12h 57m1 stop

11:09 am - 11:46 pmSWF-ORD

13h 37m1 stop

$319Multiple Airlines

Find Deal

Thu, Jan 15 - Mon, Jan 19

5:32 pm - 10:19 amORD-SWF

15h 47m1 stop

11:09 am - 7:17 pmSWF-ORD

9h 08m1 stop

$323Multiple Airlines

Find Deal

Thu, Jan 15 - Mon, Jan 19

8:22 pm - 10:19 amORD-SWF

12h 57m1 stop

11:09 am - 7:17 pmSWF-ORD

9h 08m1 stop

$326Multiple Airlines

Find Deal

Thu, Jan 15 - Mon, Jan 19

8:22 pm - 10:19 amORD-SWF

12h 57m1 stop

11:09 am - 8:54 pmSWF-ORD

10h 45m1 stop

$328Multiple Airlines

Find Deal

Thu, Jan 15 - Mon, Jan 19

7:57 pm - 6:06 pmORD-SWF

21h 09m2 stops

8:25 pm - 11:14 amSWF-ORD

15h 49m1 stop

$347Multiple Airlines

Find Deal

Thu, Dec 18 - Mon, Dec 22

6:33 pm - 6:06 pmMDW-SWF

22h 33m2 stops

11:43 am - 9:04 pmSWF-MDW

10h 21m1 stop

$354Multiple Airlines

Find Deal

Thu, Dec 18 - Sun, Dec 21

7:57 pm - 6:06 pmORD-SWF

21h 09m2 stops

8:25 pm - 11:14 amSWF-ORD

15h 49m1 stop

$356Multiple Airlines

Find Deal

Thu, Dec 18 - Mon, Dec 22

3:26 pm - 10:07 amORD-SWF

17h 41m1 stop

12:17 pm - 11:13 pmSWF-ORD

11h 56m1 stop

$385Multiple Airlines

Find Deal

Sun, Nov 23 - Wed, Nov 26

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/11

4:49 pm-11:37 am

2 stops17h 48m

New Windsor Stewart

Mon 12/15

12:27 pm-12:09 am

1 stop12h 42m

$221

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-12:09 am

1 stop12h 42m

$229

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 1/19

11:09 am-11:46 pm

1 stop13h 37m

$319

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

5:32 pm-10:19 am

1 stop15h 47m

New Windsor Stewart

Mon 1/19

11:09 am-7:17 pm

1 stop9h 08m

$323

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 1/19

11:09 am-7:17 pm

1 stop9h 08m

$326

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 1/19

11:09 am-8:54 pm

1 stop10h 45m

$328

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/18

7:57 pm-6:06 pm

2 stops21h 09m

New Windsor Stewart

Mon 12/22

8:25 pm-11:14 am

1 stop15h 49m

$347

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 12/18

6:33 pm-6:06 pm

2 stops22h 33m

New Windsor Stewart

Sun 12/21

11:43 am-9:04 pm

1 stop10h 21m

$354

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/18

7:57 pm-6:06 pm

2 stops21h 09m

New Windsor Stewart

Mon 12/22

8:25 pm-11:14 am

1 stop15h 49m

$356

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 11/23

3:26 pm-10:07 am

1 stop17h 41m

New Windsor Stewart

Wed 11/26

12:17 pm-11:13 pm

1 stop11h 56m

$385

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

Direct flights	None

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 10h 20m 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.