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Westchester County

$90+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — HPN
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
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 January 20, 2026.

This JetBlue deal was found by Cheapflights users on 1/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/311:35 pm
LGA
-
HPN
1 stop9h 26m
JetBlue
Tue 2/37:00 am
HPN
-
LGA
1 stop6h 20m
JetBlue
Deal found 1/17$293
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Sat 2/1410:00 pm
EWR
-
HPN
1 stop14h 40m
Multiple Airlines
Sun 2/221:20 pm
HPN
-
EWR
1 stop18h 39m
Multiple Airlines
Deal found 1/18$324
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Wed 4/11:59 pm
EWR
-
HPN
1 stop21h 29m
Multiple Airlines
Mon 4/612:08 pm
HPN
-
EWR
1 stop7h 52m
Multiple Airlines
Deal found 1/19$349
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Fri 2/278:00 am
LGA
-
HPN
2 stops12h 59m
Multiple Airlines
Sun 3/11:20 pm
HPN
-
LGA
1 stop10h 18m
Multiple Airlines
Deal found 1/18$358
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Sat 2/146:39 pm
LGA
-
HPN
1 stop18h 01m
Multiple Airlines
Sun 2/221:20 pm
HPN
-
LGA
1 stop10h 18m
Multiple Airlines
Deal found 1/18$369
This Expedia deal was found by Cheapflights users on 1/18. 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.
Fri 2/278:30 pm
JFK
-
HPN
1 stop13h 31m
JetBlue
Sun 3/18:30 pm
HPN
-
JFK
1 stop12h 09m
JetBlue
Deal found 1/18$385
This JetBlue deal was found by Cheapflights users on 1/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/311:15 am
EWR
-
HPN
1 stop7h 16m
JetBlue
Sat 2/77:30 am
HPN
-
EWR
1 stop9h 35m
JetBlue
Deal found 1/19$409
This JetBlue deal was found by Cheapflights users on 1/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/287:29 am
JFK
-
HPN
1 stop10h 13m
JetBlue
Sat 1/317:00 am
HPN
-
JFK
1 stop7h 42m
JetBlue
Deal found 1/17$411
This JetBlue deal was found by Cheapflights users on 1/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/39:45 am
JFK
-
HPN
1 stop8h 46m
JetBlue
Sat 2/77:30 am
HPN
-
JFK
1 stop7h 58m
JetBlue
Deal found 1/19$419
This JetBlue deal was found by Cheapflights users on 1/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/37:30 am
LGA
-
HPN
1 stop6h 38m
JetBlue
Sat 2/77:30 am
HPN
-
LGA
1 stop7h 33m
JetBlue
Deal found 1/19$445
This American Airlines deal was found by Cheapflights users on 1/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:18 pm
LGA
-
HPN
1 stop21h 41m
American Airlines
Sun 3/15:30 pm
HPN
-
LGA
1 stop17h 51m
American Airlines
Deal found 1/18$498
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:50 pm
BDL
-
HPN
1 stop15h 54m
Delta
Sun 4/196:44 pm
HPN
-
BDL
1 stop27h 04m
Delta
Deal found 1/19$505

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 January 20, 2026.

Round-trip from

$293
(JetBlue)

One-way from

$90
(Kiwi.com)

Popular in

April

Cheapest in

December
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

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 January 20, 2026.
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

Sat 1/31

1:35 pm-11:01 pm

1 stop9h 26m

White Plains Westchester County

Tue 2/3

7:00 am-1:20 pm

1 stop6h 20m

$293

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Sat 2/14

10:00 pm-12:40 pm

1 stop14h 40m

White Plains Westchester County

Sun 2/22

1:20 pm-7:59 am

1 stop18h 39m

$324

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Fri 2/27

8:00 am-8:59 pm

2 stops12h 59m

White Plains Westchester County

Sun 3/1

1:20 pm-11:38 pm

1 stop10h 18m

$358

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Sat 2/14

6:39 pm-12:40 pm

1 stop18h 01m

White Plains Westchester County

Sun 2/22

1:20 pm-11:38 pm

1 stop10h 18m

$369

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Fri 2/27

8:30 pm-10:01 am

1 stop13h 31m

White Plains Westchester County

Sun 3/1

8:30 pm-8:39 am

1 stop12h 09m

$385

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Wed 4/1

1:59 pm-11:28 am

1 stop21h 29m

White Plains Westchester County

Mon 4/6

12:08 pm-7:51 am

2 stops19h 43m

$393

NewarkWhite Plains

EWR - HPN

EWRHPN

Newark

Tue 2/3

11:15 am-6:31 pm

1 stop7h 16m

White Plains Westchester County

Sat 2/7

7:30 am-5:05 pm

1 stop9h 35m

$409

New YorkWhite Plains

JFK - HPN

JFKHPN

New York John F Kennedy Intl

Tue 2/3

9:45 am-6:31 pm

1 stop8h 46m

White Plains Westchester County

Sat 2/7

7:30 am-3:28 pm

1 stop7h 58m

$419

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Tue 2/3

7:30 am-2:08 pm

1 stop6h 38m

White Plains Westchester County

Sat 2/7

7:30 am-3:03 pm

1 stop7h 33m

$445

New YorkWhite Plains

LGA - HPN

LGAHPN

New York LaGuardia

Wed 4/1

7:35 am-8:08 pm

1 stop12h 33m

White Plains Westchester County

Mon 4/6

5:30 pm-7:08 am

1 stop13h 38m

$498

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 50 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 $293, JetBlue can have you in Westchester County from Connecticut in 9h 26m. 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.

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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