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Westchester County

$111+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — HPN
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Thu 12/187:30 amPVD - HPN
1 stop11h 30mBreeze Airways
Fri 12/191:20 pmHPN - PVD
1 stop22h 21mBreeze Airways
Deal found 12/17$551
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/188:29 pmJFK - HPN
1 stop45h 54mAmerican Airlines
Sat 1/36:30 amHPN - JFK
1 stop48h 55mAmerican Airlines
Deal found 12/16$622
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:45 amLGA - HPN
1 stop12h 21mAmerican Airlines
Wed 12/246:30 amHPN - LGA
1 stop49h 57mAmerican Airlines
Deal found 12/16$665
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/178:25 amJFK - HPN
1 stop9h 44mAmerican Airlines
Wed 12/246:30 amHPN - JFK
1 stop8h 44mAmerican Airlines
Deal found 12/16$715
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 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
Wed 12/248:00 amHPN - LGA
2 stops11h 30mMultiple Airlines
Deal found 12/16$720
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:52 pmLGA - HPN
1 stop7h 35mAmerican Airlines
Sat 1/35:16 pmHPN - LGA
1 stop29h 08mAmerican Airlines
Deal found 12/16$743
This Expedia deal was found by Cheapflights users on 12/16. 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.
Wed 12/176:30 amJFK - HPN
2 stops10h 16mMultiple Airlines
Wed 12/249:23 amHPN - JFK
2 stops12h 07mMultiple Airlines
Deal found 12/16$748
This JetBlue deal was found by Cheapflights users on 12/16. 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.
Wed 12/311:55 pmBDL - HPN
1 stop9h 09mJetBlue
Sun 1/41:00 pmHPN - BDL
1 stop10h 56mJetBlue
Deal found 12/16$815
This Expedia deal was found by Cheapflights users on 12/16. 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.
Wed 12/176:00 amEWR - HPN
1 stop7h 35mJetBlue
Wed 12/242:25 pmHPN - EWR
1 stop9h 23mJetBlue
Deal found 12/16$846
This KAYAK deal was found by Cheapflights users on 12/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:45 amLGA - HPN
1 stop12h 40mJetBlue
Fri 12/192:25 pmHPN - LGA
1 stop20h 32mJetBlue
Deal found 12/16$887
This JetBlue deal was found by Cheapflights users on 12/16. 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.
Sun 12/211:55 pmBDL - HPN
1 stop9h 09mJetBlue
Sun 12/281:00 pmHPN - BDL
1 stop10h 56mJetBlue
Deal found 12/16$935
This Delta deal was found by Cheapflights users on 12/17. 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.
Fri 12/266:00 amBDL - HPN
1 stop16h 09mDelta
Mon 12/296:03 amHPN - BDL
1 stop11h 57mDelta
Deal found 12/17$1,011

Find 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 December 18, 2025.

Round-trip from

$204
(Kiwi.com)

One-way from

$111
(JetBlue)

Popular in

April

Cheapest in

December

Average price

$104
From Connecticut to Westchester County
Search Deals
One-way flight from Connecticut to Westchester County
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
Average for round-trip flights in December 2025
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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 December 18, 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

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Mon 1/12

6:00 pm-11:28 am

2 stops17h 28m

White Plains Westchester County

Mon 1/19

8:00 am-6:59 pm

1 stop10h 59m

$204

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Fri 1/30

2:59 pm-10:30 pm

1 stop7h 31m

White Plains Westchester County

Mon 3/2

3:05 pm-11:54 pm

1 stop8h 49m

$211

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Mon 1/12

12:30 pm-11:28 am

2 stops22h 58m

White Plains Westchester County

Mon 1/19

12:08 pm-7:33 pm

1 stop7h 25m

$227

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Sat 2/7

8:25 am-4:28 pm

1 stop8h 03m

White Plains Westchester County

Mon 2/9

7:00 am-9:41 am

1 stop26h 41m

$228

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Wed 1/28

7:29 am-5:42 pm

1 stop10h 13m

White Plains Westchester County

Tue 3/3

3:05 pm-11:54 pm

1 stop8h 49m

$239

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Sat 1/31

6:59 am-5:42 pm

1 stop10h 43m

White Plains Westchester County

Tue 3/3

3:05 pm-11:54 pm

1 stop8h 49m

$239

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Wed 1/14

12:45 pm-12:40 pm

1 stop23h 55m

White Plains Westchester County

Wed 1/21

1:17 pm-11:27 pm

2 stops10h 10m

$244

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Sat 2/7

3:59 pm-10:50 am

1 stop18h 51m

White Plains Westchester County

Mon 2/9

7:30 pm-10:57 am

1 stop15h 27m

$249

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Tue 2/3

11:30 am-10:30 pm

1 stop11h 00m

White Plains Westchester County

Tue 3/3

3:05 pm-10:57 pm

1 stop7h 52m

$254

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Tue 2/3

11:30 am-10:30 pm

1 stop11h 00m

White Plains Westchester County

Mon 3/2

3:05 pm-11:54 pm

1 stop8h 49m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 43 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 $211, JetBlue can have you in Westchester County from Connecticut in 7h 31m. The distance between Connecticut and Westchester County is about 30 mi.

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