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Stewart

$148+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SWF
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Round-trip from

$292
(Kiwi.com)

One-way from

$148
(Kiwi.com)

Popular in

April

Cheapest in

May

Average price

$251
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. 24% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 18% potential price decrease ($43 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/48:10 pmPVD - SWF
1 stop20h 44mMultiple Airlines
Sun 12/76:28 pmSWF - PVD
1 stop28h 20mMultiple Airlines
Deal found 11/1$285
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/136:05 amPVD - SWF
1 stop6h 37mMultiple Airlines
Mon 11/1712:01 pmSWF - PVD
2 stops11h 29mMultiple Airlines
Deal found 11/1$328
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/166:05 amPVD - SWF
1 stop6h 37mMultiple Airlines
Thu 11/206:23 pmSWF - PVD
1 stop28h 25mMultiple Airlines
Deal found 11/1$481
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Mon 12/110:51 amPVD - SWF
1 stop8h 40mMultiple Airlines
Mon 12/812:24 pmSWF - PVD
1 stop10h 51mMultiple Airlines
Deal found 11/2$505
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/29:14 pmPVD - SWF
1 stop22h 02mMultiple Airlines
Sun 12/76:28 pmSWF - PVD
1 stop28h 20mMultiple Airlines
Deal found 11/2$613
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Tue 11/2511:11 amPVD - SWF
1 stop22h 40mMultiple Airlines
Sun 11/306:04 pmSWF - PVD
1 stop28h 44mMultiple Airlines
Deal found 11/2$621
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/286:05 amPVD - SWF
1 stop11h 33mMultiple Airlines
Thu 1/111:43 amSWF - PVD
2 stops11h 28mMultiple Airlines
Deal found 11/2$643

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 November 3, 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

Thu 12/4

8:10 pm-4:54 pm

1 stop20h 44m

New Windsor Stewart

Sun 12/7

6:28 pm-10:48 pm

1 stop28h 20m

$285

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 11/13

6:05 am-12:42 pm

1 stop6h 37m

New Windsor Stewart

Mon 11/17

12:01 pm-11:30 pm

2 stops11h 29m

$328

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sun 11/16

6:05 am-12:42 pm

1 stop6h 37m

New Windsor Stewart

Thu 11/20

6:23 pm-10:48 pm

1 stop28h 25m

$481

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Mon 12/1

10:51 am-7:31 pm

1 stop8h 40m

New Windsor Stewart

Mon 12/8

12:24 pm-11:15 pm

1 stop10h 51m

$505

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Tue 11/25

11:11 am-9:51 am

1 stop22h 40m

New Windsor Stewart

Sun 11/30

6:04 pm-10:48 pm

1 stop28h 44m

$621

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sun 12/28

6:05 am-5:38 pm

1 stop11h 33m

New Windsor Stewart

Thu 1/1

11:43 am-11:11 pm

2 stops11h 28m

$643

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 11/6

6:05 am-12:42 pm

1 stop6h 37m

New Windsor Stewart

Sun 11/9

6:14 pm-10:07 pm

1 stop27h 53m

$729

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Wed 11/19

6:00 am-10:22 am

2 stops52h 22m

$148

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sat 12/6

8:00 am-11:03 am

1 stop27h 03m

$171

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Wed 12/10

12:26 pm-11:37 am

3 stops47h 11m

$173

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 17 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.

  • 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.

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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