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Westchester County

$105+ Cheap flights from Connecticut to Westchester County

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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — HPN
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Connecticut to Westchester County

Keep the following information in mind while searching for Connecticut to Westchester County flight deals. Data was last updated September 17, 2025.

Round-trip from

$223
(JetBlue)

One-way from

$105
(Kiwi.com)
From Connecticut to Westchester County
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One-way flight from Connecticut to Westchester County
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Find flight deals from Connecticut to Westchester County

Cheapest flights from Connecticut to Westchester County
Explore the most affordable flight options available from Connecticut to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:29 amLGA - HPN
1 stop7h 37mJetBlue
Wed 11/191:00 pmHPN - LGA
1 stop7h 30mJetBlue
Deal found 9/14$223
This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/43:30 pmJFK - HPN
1 stop7h 52mJetBlue
Wed 11/191:00 pmHPN - JFK
1 stop10h 36mJetBlue
Deal found 9/14$223
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/38:00 pmEWR - HPN
1 stop14h 06mJetBlue
Mon 10/68:55 pmHPN - EWR
1 stop13h 04mJetBlue
Deal found 9/15$253
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1411:00 amEWR - HPN
1 stop8h 03mJetBlue
Wed 10/157:30 amHPN - EWR
1 stop9h 12mJetBlue
Deal found 9/16$273
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/142:59 pmLGA - HPN
1 stop8h 21mJetBlue
Tue 10/217:30 amHPN - LGA
1 stop7h 30mJetBlue
Deal found 9/15$278
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/13:00 pmEWR - HPN
1 stop7h 06mJetBlue
Sat 10/47:30 amHPN - EWR
1 stop9h 28mJetBlue
Deal found 9/15$278
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/144:35 pmJFK - HPN
1 stop6h 45mJetBlue
Tue 10/211:00 pmHPN - JFK
1 stop9h 56mJetBlue
Deal found 9/16$283
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1410:55 amLGA - HPN
1 stop8h 08mJetBlue
Wed 10/157:30 amHPN - LGA
1 stop7h 30mJetBlue
Deal found 9/16$293
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/144:35 pmJFK - HPN
1 stop6h 45mJetBlue
Wed 10/157:30 amHPN - JFK
1 stop9h 19mJetBlue
Deal found 9/16$298
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/36:45 amEWR - HPN
1 stop4h 43mMultiple Airlines
Sun 10/58:00 amHPN - EWR
2 stops26h 10mMultiple Airlines
Deal found 9/15$324
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 9/289:59 amLGA - HPN
2 stops25h 29mMultiple Airlines
Wed 10/11:14 pmHPN - LGA
1 stop26h 54mMultiple Airlines
Deal found 9/15$333
This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/232:57 pmLGA - HPN
1 stop8h 09mJetBlue
Sat 9/277:30 amHPN - LGA
1 stop6h 33mJetBlue
Deal found 9/14$348

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Westchester County 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 17, 2025.
Use the filters below to find and compare flights from Connecticut to Westchester County that are best for you.

Fly from

Connecticut

Fly to

Westchester County

Route

Depart

Return

Price

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Tue 11/4

6:29 am-2:06 pm

1 stop7h 37m

White Plains Westchester County

Wed 11/19

1:00 pm-8:30 pm

1 stop7h 30m

$223

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Tue 11/4

3:30 pm-11:22 pm

1 stop7h 52m

White Plains Westchester County

Wed 11/19

1:00 pm-11:36 pm

1 stop10h 36m

$223

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Fri 10/3

8:00 pm-10:06 am

1 stop14h 06m

White Plains Westchester County

Mon 10/6

8:55 pm-9:59 am

1 stop13h 04m

$253

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Tue 10/14

11:00 am-7:03 pm

1 stop8h 03m

White Plains Westchester County

Wed 10/15

7:30 am-4:42 pm

1 stop9h 12m

$273

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Tue 10/14

2:59 pm-11:20 pm

1 stop8h 21m

White Plains Westchester County

Tue 10/21

7:30 am-3:00 pm

1 stop7h 30m

$278

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Wed 10/1

3:00 pm-10:06 pm

1 stop7h 06m

White Plains Westchester County

Sat 10/4

7:30 am-4:58 pm

1 stop9h 28m

$278

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Tue 10/14

4:35 pm-11:20 pm

1 stop6h 45m

White Plains Westchester County

Tue 10/21

1:00 pm-10:56 pm

1 stop9h 56m

$283

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Tue 10/14

10:55 am-7:03 pm

1 stop8h 08m

White Plains Westchester County

Wed 10/15

7:30 am-3:00 pm

1 stop7h 30m

$293

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Tue 10/14

4:35 pm-11:20 pm

1 stop6h 45m

White Plains Westchester County

Wed 10/15

7:30 am-4:49 pm

1 stop9h 19m

$298

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Sun 9/28

9:59 am-11:28 am

2 stops25h 29m

White Plains Westchester County

Wed 10/1

1:14 pm-4:08 pm

1 stop26h 54m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 59 results
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Best time to book a flight from Connecticut to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County 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 Westchester County
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 Westchester County. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Connecticut to Westchester County?

    For as low as $223, JetBlue can have you in Westchester County from Connecticut in 7h 37m. The distance between Connecticut and Westchester County is about 22 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

  • How can I find direct flights from Connecticut to Westchester County?

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

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

    Yes. Cheapflights offers flight deals from Connecticut to Westchester County 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 Westchester County?

    Currently, January is the cheapest month in which you can book a flight from Connecticut to Westchester County (average of $276). Flying from Connecticut to Westchester County in March is currently the most expensive (average of $338). 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

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Alternative routes for Connecticut to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
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