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Westchester County

$41+ Cheap flights from 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MCO
Mai 17 — Mai 241
So 5/17
So 5/24
1 adult, Economy
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Find flights from Westchester County within your budget

 
Find flights departing from Westchester County that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on April 17, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

White PlainsRaleigh

HPN - RDU

HPNRDU

White Plains Westchester County

Fr 6/5

6:09 pm-7:49 pm

Nonstop1h 40m

Raleigh-Durham

Mo 6/8

3:47 pm-5:29 pm

Nonstop1h 42m

$112

White PlainsRaleigh

HPN - RDU

HPNRDU

White Plains Westchester County

Sa 7/11

12:00 pm-1:50 pm

Nonstop1h 50m

Raleigh-Durham

Mo 7/13

3:47 pm-5:29 pm

Nonstop1h 42m

$147

White PlainsRaleigh

HPN - RDU

HPNRDU

White Plains Westchester County

Fr 5/15

6:09 pm-7:49 pm

Nonstop1h 40m

Raleigh-Durham

Mo 5/18

3:47 pm-5:29 pm

Nonstop1h 42m

$148

White PlainsRaleigh

HPN - RDU

HPNRDU

White Plains Westchester County

Mo 5/11

6:09 pm-7:49 pm

Nonstop1h 40m

Raleigh-Durham

Mo 5/18

3:47 pm-5:29 pm

Nonstop1h 42m

$148

White PlainsRaleigh

HPN - RDU

HPNRDU

White Plains Westchester County

Fr 10/9

7:40 pm-9:27 pm

Nonstop1h 47m

Raleigh-Durham

So 10/11

7:17 pm-8:59 pm

Nonstop1h 42m

$153

White PlainsRaleigh

HPN - RDU

HPNRDU

White Plains Westchester County

Fr 9/4

6:09 pm-7:49 pm

Nonstop1h 40m

Raleigh-Durham

Mo 9/7

3:47 pm-5:29 pm

Nonstop1h 42m

$158

White PlainsRaleigh

HPN - RDU

HPNRDU

White Plains Westchester County

Fr 6/26

6:09 pm-7:49 pm

Nonstop1h 40m

Raleigh-Durham

Di 6/30

10:51 am-12:33 pm

Nonstop1h 42m

$178

White PlainsCharleston

HPN - CHS

HPNCHS

White Plains Westchester County

Do 8/27

12:07 pm-2:13 pm

Nonstop2h 06m

Charleston

Fr 9/4

6:40 pm-8:49 pm

Nonstop2h 09m

$188

White PlainsCharleston

HPN - CHS

HPNCHS

White Plains Westchester County

Sa 6/13

8:00 am-10:06 am

Nonstop2h 06m

Charleston

Di 6/16

9:18 am-11:27 am

Nonstop2h 09m

$189

White PlainsWest Palm Beach

HPN - PBI

HPNPBI

White Plains Westchester County

Mo 6/8

7:55 am-10:43 am

Nonstop2h 48m

Palm Beach Intl

Sa 6/20

8:06 pm-11:00 pm

Nonstop2h 54m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Westchester County

Have a flexible travel schedule? Discover the best time to fly from Westchester County 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.

Travel insights for flights from Westchester County

Get recent, data-driven insights about flights from Westchester County including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Westchester County?

Currently, July is the cheapest month in which you can book a flight from Westchester County (average of $68). Flying from Westchester County in April will prove the most costly (average of $167). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Westchester County?

Use this chart to determine the cheapest time to fly round-trip from Westchester County to Orlando. Price data was last updated on April 11, 2026.

Those who are seeking the cheapest fare on flights departing from Westchester County would be wise to consider leaving during Wednesday afternoons when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Monday mornings when fares are usually the most expensive.

Which airlines fly from Westchester County?

For flights departing from Westchester County check dates and pricing for the following: JetBlue, Breeze Airways, American Airlines, Delta, Frontier. These airlines depart to the following popular destinations: Orlando.

JetBlue
JetBlue
From $89
American Airlines
American Airlines
From $151
Delta
Delta
From $42
Breeze Airways
Breeze Airways
From $83

Airline reviews for flights from Westchester County

Read reviews and ratings of airlines operating flights from Westchester County. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Westchester County travel. Please note that the reviews are sourced from user searches and were last updated on April 17, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Get a feel of what it's like to fly with Breeze Airways,Delta, andJetBlue from Westchester County by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
279 reviews

Food

6.6

Crew

8.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.1
Very good
279 reviews
Breeze Airways
8.1
Very good
279 reviews

Food

6.6

Crew

8.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Delta
7.9
Good
8,409 reviews
Breeze Airways
8.1
Very good
279 reviews

Food

6.6

Crew

8.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
JetBlue
7.2
Good
2,939 reviews
Breeze Airways
8.1
Very good
279 reviews

Food

6.6

Crew

8.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
American Airlines
7.1
Good
11,594 reviews
Breeze Airways
8.1
Very good
279 reviews

Food

6.6

Crew

8.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Frontier
5.7
Fair
2,987 reviews
Breeze Airways
8.1
Very good
279 reviews

Food

6.6

Crew

8.7

Overall

8.1

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

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Related info for your journey

Access useful and relevant information related to your journey from Westchester County. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated April 17, 2026.

  • What is the cheapest airport to fly out of Westchester County?

    Valencia airport offers the cheapest routes to New York, from $15; whereas Medellín Jose Maria Cordova Intl airport is typically cheaper if you're flying to Panama City, from $20. It's best to make sure you are flexible on dates to find the cheapest possible flight options for your journey.

  • What is the cheapest month to fly from Westchester County?

    July is currently the cheapest month to fly from Westchester County. At this moment in time April is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Westchester County?

    Check out the cheapest flights from Westchester County to embark to:
    Fly from Valencia to Palma de Mallorca from $15 round trip
    Fly from Medellín to Cartagena from $20 round trip
    Fly from Barcelona to Ibiza from $20 round trip
    Fly from Medellín to Santa Marta from $22 round trip
    Fly from Istanbul to Ankara from $23 round trip

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