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 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.

$88 Cheap Flights from Chicago to New Windsor in 2025/26

1 adult

0 bags

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4:21 pm - 11:37 amORD-SWF

18h 16m1 stop

12:27 pm - 8:01 pmSWF-ORD

8h 34m1 stop

$215Multiple Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

1:26 pm - 10:41 amORD-SWF

20h 15m2 stops

12:01 pm - 12:27 amSWF-ORD

13h 26m1 stop

$236Multiple Airlines

Find Deal

Thu, Oct 30 - Mon, Nov 3

12:29 pm - 11:37 amORD-SWF

22h 08m2 stops

12:27 pm - 8:01 pmSWF-ORD

8h 34m1 stop

$254Multiple Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

11:48 am - 10:07 amORD-SWF

21h 19m1 stop

12:17 pm - 4:25 pmSWF-ORD

29h 08m1 stop

$304Multiple Airlines

Find Deal

Sun, Nov 23 - Wed, Nov 26

12:32 pm - 10:07 amORD-SWF

20h 35m2 stops

12:17 pm - 4:25 pmSWF-ORD

29h 08m1 stop

$307Multiple Airlines

Find Deal

Sun, Nov 23 - Wed, Nov 26

4:21 pm - 11:37 amORD-SWF

18h 16m1 stop

6:56 pm - 11:14 amSWF-ORD

17h 18m1 stop

$341Multiple Airlines

Find Deal

Thu, Dec 4 - Fri, Dec 19

10:52 am - 10:41 amORD-SWF

22h 49m1 stop

11:43 am - 10:41 amSWF-ORD

23h 58m2 stops

$357Multiple Airlines

Find Deal

Thu, Nov 6 - Sun, Nov 9

8:20 am - 10:07 amORD-SWF

24h 47m2 stops

12:17 pm - 11:06 pmSWF-ORD

11h 49m2 stops

$362Multiple Airlines

Find Deal

Sun, Nov 23 - Wed, Nov 26

4:12 pm - 10:26 amMDW-SWF

17h 14m2 stops

7:28 pm - 9:32 amSWF-MDW

15h 04m1 stop

$386Allegiant Air

Find Deal

Mon, Nov 17 - Mon, Nov 24

4:58 pm - 8:53 amORD-SWF

14h 55m1 stop

5:49 pm - 8:27 pmSWF-ORD

27h 38m2 stops

$387Multiple Airlines

Find Deal

Mon, Nov 24 - Mon, Dec 1

Fly from

Fly to

Route

Depart

Return

Price

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-8:01 pm

1 stop8h 34m

$215

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/30

1:26 pm-10:41 am

2 stops20h 15m

New Windsor Stewart

Mon 11/3

12:01 pm-12:27 am

1 stop13h 26m

$236

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/4

12:29 pm-11:37 am

2 stops22h 08m

New Windsor Stewart

Mon 12/8

12:27 pm-8:01 pm

1 stop8h 34m

$254

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 11/23

11:48 am-10:07 am

1 stop21h 19m

New Windsor Stewart

Wed 11/26

12:17 pm-4:25 pm

1 stop29h 08m

$304

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 11/23

12:32 pm-10:07 am

2 stops20h 35m

New Windsor Stewart

Wed 11/26

12:17 pm-4:25 pm

1 stop29h 08m

$307

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/4

4:21 pm-11:37 am

1 stop18h 16m

New Windsor Stewart

Fri 12/19

6:56 pm-11:14 am

1 stop17h 18m

$341

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/6

10:52 am-10:41 am

1 stop22h 49m

New Windsor Stewart

Sun 11/9

11:43 am-10:41 am

2 stops23h 58m

$357

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 11/23

8:20 am-10:07 am

2 stops24h 47m

New Windsor Stewart

Wed 11/26

12:17 pm-11:06 pm

2 stops11h 49m

$362

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Mon 11/17

4:12 pm-10:26 am

2 stops17h 14m

New Windsor Stewart

Mon 11/24

7:28 pm-9:32 am

1 stop15h 04m

$386

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 11/24

4:58 pm-8:53 am

1 stop14h 55m

New Windsor Stewart

Mon 12/1

5:49 pm-8:27 pm

2 stops27h 38m

$387

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 9h 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 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.