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Westchester County

$97+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — HPN
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
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 November 19, 2025.

Round-trip from

$265
(JetBlue)

One-way from

$97
(Kiwi.com)

Popular in

April

Cheapest in

May

Average price

$133
From Connecticut to Westchester County
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One-way flight from Connecticut to Westchester County
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Highest demand for flights based on searches. 39% potential increase in price ($189 potential increase over avg. RT price).
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Cheapest flight prices on average. 40% potential price decrease ($83 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 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 November 19, 2025.

This JetBlue deal was found by Cheapflights users on 11/18. 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.
Sat 12/612:08 pmBDL - HPN
1 stop7h 22mJetBlue
Wed 12/101:00 pmHPN - BDL
1 stop10h 59mJetBlue
Deal found 11/18$265
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/157:00 amLGA - HPN
1 stop13h 45mMultiple Airlines
Mon 12/228:00 amHPN - LGA
1 stop12h 59mMultiple Airlines
Deal found 11/17$274
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/156:07 amEWR - HPN
1 stop14h 38mMultiple Airlines
Mon 12/228:00 amHPN - EWR
1 stop23h 56mMultiple Airlines
Deal found 11/17$312
This Delta deal was found by Cheapflights users on 11/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:00 amJFK - HPN
1 stop16h 09mDelta
Wed 12/1012:45 pmHPN - JFK
1 stop12h 22mDelta
Deal found 11/17$323
This JetBlue deal was found by Cheapflights users on 11/18. 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 12/106:00 amPVD - HPN
1 stop7h 35mJetBlue
Sat 12/132:30 pmHPN - PVD
1 stop6h 59mJetBlue
Deal found 11/18$338
This Expedia deal was found by Cheapflights users on 11/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/166:30 amJFK - HPN
1 stop7h 05mJetBlue
Tue 12/239:20 pmHPN - JFK
1 stop12h 19mJetBlue
Deal found 11/16$411
This Expedia deal was found by Cheapflights users on 11/18. 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.
Wed 12/177:30 amJFK - HPN
1 stop6h 44mJetBlue
Sat 12/202:25 pmHPN - JFK
1 stop8h 49mJetBlue
Deal found 11/18$418
This Expedia deal was found by Cheapflights users on 11/18. 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.
Wed 12/177:30 amLGA - HPN
1 stop11h 26mJetBlue
Sat 12/202:25 pmHPN - LGA
1 stop7h 07mJetBlue
Deal found 11/18$423
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 11/204:51 pmLGA - HPN
1 stop18h 37mMultiple Airlines
Thu 11/2712:09 pmHPN - LGA
2 stops20h 51mMultiple Airlines
Deal found 11/19$434
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/177:55 pmLGA - HPN
1 stop16h 44mMultiple Airlines
Sat 12/208:00 amHPN - LGA
2 stops11h 30mMultiple Airlines
Deal found 11/18$445
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 11/2012:00 pmEWR - HPN
1 stop23h 28mMultiple Airlines
Thu 11/2712:09 pmHPN - EWR
1 stop22h 21mMultiple Airlines
Deal found 11/19$447
This Expedia deal was found by Cheapflights users on 11/18. 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.
Wed 12/1710:45 amEWR - HPN
1 stop8h 11mJetBlue
Sat 12/202:25 pmHPN - EWR
1 stop9h 57mJetBlue
Deal found 11/18$458

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 November 19, 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

HartfordWhite Plains

BDL - HPN

BDLHPN

Hartford Bradley Intl

Sat 12/6

12:08 pm-7:30 pm

1 stop7h 22m

White Plains Westchester County

Wed 12/10

1:00 pm-11:59 pm

1 stop10h 59m

$265

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Sat 1/31

1:35 pm-11:00 pm

1 stop9h 25m

White Plains Westchester County

Wed 2/4

2:00 pm-11:36 pm

1 stop9h 36m

$273

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Mon 12/15

7:00 am-8:45 pm

1 stop13h 45m

White Plains Westchester County

Mon 12/22

8:00 am-8:59 pm

1 stop12h 59m

$274

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Sat 1/31

6:00 am-6:00 pm

1 stop12h 00m

White Plains Westchester County

Wed 2/4

10:29 am-11:55 pm

1 stop13h 26m

$303

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Mon 12/15

6:07 am-8:45 pm

1 stop14h 38m

White Plains Westchester County

Mon 12/22

8:00 am-7:56 am

1 stop23h 56m

$312

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Sat 12/6

6:00 am-10:09 pm

1 stop16h 09m

White Plains Westchester County

Wed 12/10

12:45 pm-1:07 am

1 stop12h 22m

$323

ProvidenceWhite Plains

PVD - HPN

PVDHPN

Providence-TFGreen

Wed 12/10

6:00 am-1:35 pm

1 stop7h 35m

White Plains Westchester County

Sat 12/13

2:30 pm-9:29 pm

1 stop6h 59m

$338

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Sat 1/10

8:30 pm-12:06 pm

1 stop15h 36m

White Plains Westchester County

Fri 4/17

6:40 pm-10:18 pm

1 stop27h 38m

$353

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Thu 1/8

12:25 pm-10:00 pm

1 stop9h 35m

White Plains Westchester County

Mon 4/13

6:00 am-10:18 pm

1 stop16h 18m

$376

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Tue 1/6

7:00 am-6:00 pm

1 stop11h 00m

White Plains Westchester County

Fri 4/17

6:40 pm-10:18 pm

1 stop27h 38m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 60 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 $265, JetBlue can have you in Westchester County from Connecticut in 7h 22m. The distance between Connecticut and Westchester County is about 80 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.

See more FAQs

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