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Stewart

$133+ Cheap flights from Connecticut to New Windsor (SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SWF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Connecticut to Stewart

Keep the following information in mind while searching for Connecticut to Stewart flight deals. Data was last updated September 11, 2025.

Round-trip from

$341
(Kiwi.com)

One-way from

$133
(Kiwi.com)

Popular in

April

Cheapest in

May

Average price

$317
From Connecticut to New Windsor Stewart
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One-way flight from Connecticut to New Windsor Stewart
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Highest demand for flights based on searches. 12% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 14% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Connecticut to Stewart

Cheapest flights from Connecticut to Stewart
Explore the most affordable flight options available from Connecticut to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/126:05 amPVD - SWF
1 stop10h 50mMultiple Airlines
Mon 10/138:21 pmSWF - PVD
1 stop20h 30mMultiple Airlines
Deal found 9/11$341
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:14 pmPVD - SWF
1 stop23h 17mMultiple Airlines
Thu 10/167:11 pmSWF - PVD
1 stop26h 56mMultiple Airlines
Deal found 9/11$449
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/113:42 pmPVD - SWF
1 stop19h 21mMultiple Airlines
Fri 10/1012:24 pmSWF - PVD
1 stop11h 06mMultiple Airlines
Deal found 9/9$521
This FlightHub deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/253:45 pmPVD - SWF
1 stop19h 59mBreeze Airways
Mon 9/2912:24 pmSWF - PVD
1 stop11h 06mBreeze Airways
Deal found 9/9$574
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/113:45 pmPVD - SWF
1 stop19h 59mBreeze Airways
Fri 10/1012:24 pmSWF - PVD
1 stop11h 06mBreeze Airways
Deal found 9/9$730
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/93:00 pmBDL - SWF
1 stop20h 44mBreeze Airways
Thu 10/1611:43 amSWF - BDL
2 stops11h 23mBreeze Airways
Deal found 9/11$767

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Connecticut to New Windsor that are best for you.

Fly from

Connecticut

Fly to

Stewart

Route

Depart

Return

Price

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sun 10/12

6:05 am-4:55 pm

1 stop10h 50m

New Windsor Stewart

Mon 10/13

8:21 pm-4:51 pm

1 stop20h 30m

$341

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 10/9

8:14 pm-7:31 pm

1 stop23h 17m

New Windsor Stewart

Thu 10/16

7:11 pm-10:07 pm

1 stop26h 56m

$449

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 9/25

3:45 pm-11:44 am

1 stop19h 59m

New Windsor Stewart

Mon 9/29

12:24 pm-11:30 pm

1 stop11h 06m

$574

HartfordNew Windsor

BDL - SWF

BDLSWF

Hartford Bradley Intl

Thu 10/9

3:00 pm-11:44 am

1 stop20h 44m

New Windsor Stewart

Thu 10/16

11:43 am-11:06 pm

2 stops11h 23m

$767

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sun 10/26

8:14 pm-7:16 pm

1 stop23h 02m

$133

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 10/23

6:05 am-4:55 pm

1 stop10h 50m

$153

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 11/6

6:05 am-12:42 pm

1 stop6h 37m

$155

HartfordNew Windsor

BDL - SWF

BDLSWF

Hartford Bradley Intl

Thu 10/30

3:00 pm-11:44 am

1 stop20h 44m

$160

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sun 9/21

3:42 pm-11:03 am

1 stop19h 21m

$174

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sun 10/19

8:14 pm-7:31 pm

1 stop23h 17m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 13 results
1
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Best time to book a flight from Connecticut to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Connecticut with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Connecticut to New Windsor
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Connecticut?

    If you book a flight to New Windsor from Connecticut, you will be flying to Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor.

  • How long is the flight from Connecticut to New Windsor?

    A quick flight from Connecticut to New Windsor can take about 20h 44m. Breeze Airways provides one of the quickest options available for as low as $767. There are 79 mi between Connecticut and New Windsor.

  • Can I find deals for flights from Connecticut to Stewart that include hotel bookings?

    Yes. In addition to deals on Connecticut to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Stewart.

  • Can I find deals for business class flights from Connecticut to Stewart?

    Yes. Cheapflights offers flight deals from Connecticut to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Connecticut to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Connecticut to New Windsor (average of $109). Flying from Connecticut to New Windsor in December is currently the most expensive (average of $202). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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