HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$145+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SWF
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Connecticut to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 12, 2026.

Round-trip from

$586
(Kiwi.com)

One-way from

$145
(Kiwi.com)

Popular in

April

Cheapest in

December
From Connecticut to New Windsor Stewart
Search Deals
One-way flight from Connecticut to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 44% potential increase in price ($210 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 46% potential price decrease ($86 potential savings vs. average RT price).
Search Deals

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 January 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Wed 8/196:15 am
PVD
-
SWF
1 stop5h 10m
Breeze Airways
Wed 8/2612:05 pm
SWF
-
PVD
2 stops10h 52m
Breeze Airways
Deal found 1/10$312
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Wed 8/126:15 am
PVD
-
SWF
1 stop5h 10m
Breeze Airways
Wed 8/1912:05 pm
SWF
-
PVD
2 stops10h 52m
Breeze Airways
Deal found 1/10$327
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Sat 8/226:15 am
PVD
-
SWF
1 stop5h 10m
Breeze Airways
Wed 8/2612:05 pm
SWF
-
PVD
2 stops10h 52m
Breeze Airways
Deal found 1/10$334
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Wed 8/126:15 am
PVD
-
SWF
1 stop5h 10m
Breeze Airways
Mon 8/1712:15 pm
SWF
-
PVD
1 stop11h 28m
Breeze Airways
Deal found 1/10$353
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 1/228:00 am
PVD
-
SWF
1 stop27h 31m
Multiple Airlines
Sun 1/256:49 pm
SWF
-
PVD
1 stop22h 01m
Multiple Airlines
Deal found 1/12$366
This Kiwi.com deal was found by Cheapflights users on 1/12. 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.
Sat 1/243:42 pm
PVD
-
SWF
1 stop19h 51m
Multiple Airlines
Sun 1/256:49 pm
SWF
-
PVD
1 stop22h 01m
Multiple Airlines
Deal found 1/12$375
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Sat 8/156:15 am
PVD
-
SWF
1 stop5h 10m
Breeze Airways
Wed 8/1912:05 pm
SWF
-
PVD
2 stops10h 52m
Breeze Airways
Deal found 1/10$444
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Sat 8/156:15 am
PVD
-
SWF
1 stop5h 10m
Breeze Airways
Mon 8/1712:15 pm
SWF
-
PVD
1 stop11h 28m
Breeze Airways
Deal found 1/10$471
This Kiwi.com deal was found by Cheapflights users on 1/11. 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.
Mon 2/96:00 am
PVD
-
SWF
1 stop12h 43m
Multiple Airlines
Mon 2/1612:11 pm
SWF
-
PVD
1 stop11h 25m
Multiple Airlines
Deal found 1/11$602
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Sat 2/73:42 pm
PVD
-
SWF
1 stop19h 26m
Multiple Airlines
Sat 2/145:59 pm
SWF
-
PVD
1 stop17h 28m
Multiple Airlines
Deal found 1/10$621

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 January 12, 2026.
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 1/22

8:00 am-11:31 am

1 stop27h 31m

New Windsor Stewart

Sun 1/25

6:49 pm-4:50 pm

1 stop22h 01m

$366

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sat 1/24

3:42 pm-11:33 am

1 stop19h 51m

New Windsor Stewart

Sun 1/25

6:49 pm-4:50 pm

1 stop22h 01m

$375

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Mon 2/9

6:00 am-6:43 pm

1 stop12h 43m

New Windsor Stewart

Mon 2/16

12:11 pm-11:36 pm

1 stop11h 25m

$602

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sat 2/7

3:42 pm-11:08 am

1 stop19h 26m

New Windsor Stewart

Sat 2/14

5:59 pm-11:27 am

1 stop17h 28m

$621

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sat 2/14

6:50 pm-11:08 am

1 stop16h 18m

New Windsor Stewart

Fri 2/20

12:11 pm-11:36 pm

1 stop11h 25m

$793

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 2/5

8:05 am-10:19 am

2 stops26h 14m

$145

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Sun 1/25

8:00 am-11:31 am

1 stop27h 31m

$154

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 2/5

7:10 am-11:31 am

1 stop28h 21m

$165

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 3/5

7:10 am-10:12 am

2 stops27h 02m

$187

ProvidenceNew Windsor

PVD - SWF

PVDSWF

Providence-TFGreen

Thu 2/12

8:05 am-11:31 am

2 stops27h 26m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 12 results
1
2

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

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

Currently, August is the cheapest month in which you can book a flight from Connecticut to New Windsor (average of $57). Flying from Connecticut to New Windsor in February is currently the most expensive (average of $415). 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.

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.

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

    Currently, August is the cheapest month in which you can book a flight from Connecticut to New Windsor (average of $57). Flying from Connecticut to New Windsor in February is currently the most expensive (average of $415). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Connecticut to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
San Francisco to John F Kennedy Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
O'Hare Intl to John F Kennedy Intl flights
San Francisco to Newark flights
Orlando to John F Kennedy Intl flights
Los Angeles to Newark flights
Fort Lauderdale to John F Kennedy Intl flights
Atlanta to LaGuardia flights
Los Angeles to LaGuardia flights
Hobby to LaGuardia flights
Dallas/Fort Worth to Newark flights
Hobby to John F Kennedy Intl flights
Atlanta to John F Kennedy Intl flights
Miami to LaGuardia flights
Tampa to John F Kennedy Intl flights
Fort Lauderdale to LaGuardia flights
O'Hare Intl to LaGuardia flights
Fort Lauderdale to Newark flights
Miami to John F Kennedy Intl flights
O'Hare Intl to Newark flights
Hobby to Newark flights
San Francisco to LaGuardia flights
Tampa to LaGuardia flights
Atlanta to Newark flights
Miami to Newark flights
Seattle to John F Kennedy Intl flights
Charlotte to John F Kennedy Intl flights
Denver to John F Kennedy Intl flights
Seattle to Newark flights
George Bush Intcntl to John F Kennedy Intl flights
Tampa to Newark flights
Orlando to Newark flights
West Palm Beach to Newark flights
George Bush Intcntl to LaGuardia flights
Orlando to LaGuardia flights
Denver to LaGuardia flights
Minneapolis to John F Kennedy Intl flights
Denver to Newark flights
Raleigh to LaGuardia flights
Sky Harbor Intl to John F Kennedy Intl flights
George Bush Intcntl to Newark flights
Cincinnati to John F Kennedy Intl flights
West Palm Beach to John F Kennedy Intl flights
Minneapolis to LaGuardia flights
Austin to John F Kennedy Intl flights
Charlotte to LaGuardia flights
Seattle to LaGuardia flights
Raleigh to John F Kennedy Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.