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Westchester County

$55+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MCO
abr. 27 — may. 41
lun. 4/27
lun. 5/4
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 marzo 28, 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 PlainsCharleston

HPN - CHS

HPNCHS

White Plains Westchester County

vie. 6/5

8:00 am-10:06 am

Nonstop2h 06m

Charleston

sáb. 6/6

6:21 pm-8:30 pm

Nonstop2h 09m

$163

White PlainsFort Lauderdale

HPN - FLL

HPNFLL

White Plains Westchester County

lun. 5/11

10:48 am-1:45 pm

Nonstop2h 57m

Fort Lauderdale

vie. 5/15

7:35 pm-10:39 pm

Nonstop3h 04m

$207

White PlainsFort Myers

HPN - RSW

HPNRSW

White Plains Westchester County

vie. 4/24

6:00 am-1:54 pm

1 stop7h 54m

Fort Myers SW Florida Intl

mié. 4/29

11:05 am-6:16 pm

1 stop7h 11m

$217

White PlainsWest Palm Beach

HPN - PBI

HPNPBI

White Plains Westchester County

sáb. 5/2

6:30 am-9:13 am

Nonstop2h 43m

Palm Beach Intl

mié. 5/6

8:09 pm-11:00 pm

Nonstop2h 51m

$217

White PlainsFort Myers

HPN - RSW

HPNRSW

White Plains Westchester County

sáb. 4/18

6:55 pm-12:48 am

1 stop5h 53m

Fort Myers SW Florida Intl

mar. 4/21

5:30 am-12:00 pm

1 stop6h 30m

$217

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

vie. 4/17

6:54 pm-1:18 am

1 stop6h 24m

Orlando

mar. 4/21

11:30 am-6:16 pm

1 stop6h 46m

$217

White PlainsWest Palm Beach

HPN - PBI

HPNPBI

White Plains Westchester County

sáb. 4/25

5:20 pm-12:41 am

1 stop7h 21m

Palm Beach Intl

sáb. 5/2

8:00 am-2:29 pm

1 stop6h 29m

$227

White PlainsFort Lauderdale

HPN - FLL

HPNFLL

White Plains Westchester County

sáb. 4/25

12:30 pm-6:57 pm

1 stop6h 27m

Fort Lauderdale

mié. 4/29

4:20 pm-10:03 pm

1 stop5h 43m

$227

White PlainsFort Lauderdale

HPN - FLL

HPNFLL

White Plains Westchester County

sáb. 6/6

12:31 pm-6:48 pm

1 stop6h 17m

Fort Lauderdale

mar. 6/9

6:30 am-12:09 pm

1 stop5h 39m

$227

White PlainsFort Lauderdale

HPN - FLL

HPNFLL

White Plains Westchester County

lun. 4/27

6:57 pm-12:40 am

1 stop5h 43m

Fort Lauderdale

mié. 4/29

12:25 pm-6:16 pm

1 stop5h 51m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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, October is the cheapest month in which you can book a flight from Westchester County (average of $91). Flying from Westchester County in April will prove the most costly (average of $187). 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 March 23, 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 $91

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 marzo 28, 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
274 reviews

Food

6.6

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.2

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
274 reviews
Breeze Airways
8.1
Very good
274 reviews

Food

6.6

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.2

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
8,358 reviews
Breeze Airways
8.1
Very good
274 reviews

Food

6.6

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.2

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
2,909 reviews
Breeze Airways
8.1
Very good
274 reviews

Food

6.6

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.2

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
11,520 reviews
Breeze Airways
8.1
Very good
274 reviews

Food

6.6

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.2

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
3,013 reviews
Breeze Airways
8.1
Very good
274 reviews

Food

6.6

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.2

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 marzo 28, 2026.

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

    Cartagena Rafael Nunez airport offers the cheapest routes to New York, from $23; whereas Medellín Jose Maria Cordova Intl airport is typically cheaper if you're flying to Punta Cana, from $23. 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?

    October 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 Medellín to Cartagena from $23 round trip
    Fly from Istanbul to Ankara from $23 round trip
    Fly from Cartagena to Medellín from $23 round trip
    Fly from Cheongju to Jeju City from $24 round trip
    Fly from Cartagena to Bogotá from $27 round trip

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