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Westchester County

$59+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MCO
Oct 31 — Nov 71
Fri 10/31
Fri 11/7
1 adult, Economy
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Find flights from Westchester County

Cheapest flights from Westchester County
Explore the most affordable flight options available from Westchester County. Find the lowest fares based on data from user searches, with prices last updated on October 1, 2025.

This Priceline deal was found by Cheapflights users on 9/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:30 amHPN - TPA
Nonstop2h 54mJetBlue
Wed 10/299:00 amTPA - HPN
Nonstop2h 49mJetBlue
Deal found 9/29$112
This Priceline deal was found by Cheapflights users on 9/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/31:20 pmHPN - MSY
1 stop4h 51mBreeze Airways
Thu 11/67:00 amMSY - HPN
1 stop4h 39mBreeze Airways
Deal found 9/29$115
This JetBlue deal was found by Cheapflights users on 9/30. 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 10/287:00 amHPN - FLL
Nonstop2h 53mJetBlue
Tue 10/286:40 pmFLL - HPN
Nonstop2h 57mJetBlue
Deal found 9/30$117
This JetBlue deal was found by Cheapflights users on 9/29. 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.
Thu 10/306:30 amHPN - TPA
Nonstop2h 54mJetBlue
Tue 11/119:00 amTPA - HPN
Nonstop2h 49mJetBlue
Deal found 9/29$117
This Trip.com deal was found by Cheapflights users on 9/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:30 amHPN - TPA
Nonstop2h 54mJetBlue
Mon 11/39:00 amTPA - HPN
Nonstop2h 49mJetBlue
Deal found 9/29$121
This Priceline deal was found by Cheapflights users on 9/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/281:17 pmHPN - MSY
1 stop4h 56mBreeze Airways
Mon 2/27:03 amMSY - HPN
1 stop4h 27mBreeze Airways
Deal found 9/29$122
This JetBlue deal was found by Cheapflights users on 9/30. 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 11/27:00 pmHPN - FLL
Nonstop3h 02mJetBlue
Sat 11/88:30 pmFLL - HPN
Nonstop2h 57mJetBlue
Deal found 9/30$125
This Priceline deal was found by Cheapflights users on 9/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:30 amHPN - TPA
Nonstop2h 54mJetBlue
Fri 11/212:50 pmTPA - HPN
Nonstop2h 47mJetBlue
Deal found 9/29$125
This JetBlue deal was found by Cheapflights users on 10/1. 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 11/116:30 amHPN - TPA
Nonstop2h 54mJetBlue
Fri 11/149:00 amTPA - HPN
Nonstop2h 49mJetBlue
Deal found 10/1$127
This JetBlue deal was found by Cheapflights users on 10/1. 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 11/116:30 amHPN - TPA
Nonstop2h 54mJetBlue
Thu 11/204:55 pmTPA - HPN
Nonstop2h 45mJetBlue
Deal found 10/1$130
This Priceline deal was found by Cheapflights users on 9/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/161:19 pmHPN - MSY
1 stop4h 55mBreeze Airways
Wed 11/197:10 amMSY - HPN
1 stop4h 24mBreeze Airways
Deal found 9/30$130
This Breeze Airways deal was found by Cheapflights users on 9/30. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/21:19 pmHPN - MSY
1 stop4h 55mBreeze Airways
Fri 11/77:00 amMSY - HPN
1 stop4h 40mBreeze Airways
Deal found 9/30$131

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 October 1, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Orlando

Route

Depart

Return

Price

White PlainsFort Lauderdale

HPN - FLL

HPNFLL

White Plains Westchester County

Tue 10/28

7:00 am-9:53 am

Nonstop2h 53m

Fort Lauderdale

Thu 10/30

8:25 pm-11:22 pm

Nonstop2h 57m

$117

White PlainsFort Lauderdale

HPN - FLL

HPNFLL

White Plains Westchester County

Mon 10/27

7:00 pm-10:02 pm

Nonstop3h 02m

Fort Lauderdale

Tue 10/28

8:25 pm-11:22 pm

Nonstop2h 57m

$117

White PlainsFort Lauderdale

HPN - FLL

HPNFLL

White Plains Westchester County

Tue 10/28

7:00 am-9:53 am

Nonstop2h 53m

Fort Lauderdale

Tue 10/28

6:40 pm-9:37 pm

Nonstop2h 57m

$117

White PlainsFort Lauderdale

HPN - FLL

HPNFLL

White Plains Westchester County

Wed 10/29

7:00 am-9:53 am

Nonstop2h 53m

Fort Lauderdale

Wed 10/29

8:25 pm-11:22 pm

Nonstop2h 57m

$117

White PlainsNew Orleans

HPN - MSY

HPNMSY

White Plains Westchester County

Sun 11/2

1:19 pm-5:14 pm

1 stop4h 55m

New Orleans Louis Armstrong

Fri 11/7

7:00 am-12:40 pm

1 stop4h 40m

$131

White PlainsFort Myers

HPN - RSW

HPNRSW

White Plains Westchester County

Sat 11/1

8:30 pm-11:36 pm

Nonstop3h 06m

Fort Myers SW Florida Intl

Sat 11/15

7:05 am-10:00 am

Nonstop2h 55m

$137

White PlainsTampa

HPN - TPA

HPNTPA

White Plains Westchester County

Tue 11/11

6:30 am-9:24 am

Nonstop2h 54m

Tampa

Sat 11/15

9:00 am-11:49 am

Nonstop2h 49m

$142

White PlainsWest Palm Beach

HPN - PBI

HPNPBI

White Plains Westchester County

Sun 10/26

7:30 am-10:22 am

Nonstop2h 52m

Palm Beach Intl

Thu 10/30

7:30 pm-10:19 pm

Nonstop2h 49m

$147

White PlainsWest Palm Beach

HPN - PBI

HPNPBI

White Plains Westchester County

Fri 10/31

3:08 pm-5:59 pm

Nonstop2h 51m

Palm Beach Intl

Sun 11/2

5:00 am-7:49 am

Nonstop2h 49m

$147

White PlainsFort Myers

HPN - RSW

HPNRSW

White Plains Westchester County

Sat 11/15

9:35 am-12:40 pm

Nonstop3h 05m

Fort Myers SW Florida Intl

Wed 11/19

7:05 am-10:00 am

Nonstop2h 55m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 60 results
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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 $102). Flying from Westchester County in April will prove the most costly (average of $207). 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 September 28, 2025.

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 Friday 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, American Airlines, Breeze Airways, Frontier, Delta. These airlines depart to the following popular destinations: Orlando.

JetBlue
JetBlue
From $78
American Airlines
American Airlines
From $158
Delta
Delta
From $58
Breeze Airways
Breeze Airways
From $60

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 October 1, 2025. 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 Delta, Breeze Airways, and American Airlines 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.
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Breeze Airways
8.0
Very good
210 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
11,030 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
JetBlue
7.2
Good
2,912 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Frontier
5.8
Fair
3,154 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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Popular international destinations from United States

The most popular international flight routes departing from United States we’ve come across at this time.
Flights from John F Kennedy Intl to Kuwait City
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Flights from Dulles Intl to Abu Dhabi
Flights from O'Hare Intl to Abu Dhabi
Flights from John F Kennedy Intl to Mumbai
Flights from Dulles Intl to Doha
Flights from John F Kennedy Intl to New Delhi
Flights from Los Angeles to San Salvador
Flights from San Francisco to Hong Kong
Flights from Los Angeles to Hong Kong
Flights from Los Angeles to Manila
Flights from John F Kennedy Intl to Madrid
Flights from Atlanta to Abu Dhabi
Flights from Dulles Intl to San Salvador
Flights from John F Kennedy Intl to Doha
Flights from John F Kennedy Intl to Hong Kong
Flights from Newark to New Delhi
Flights from San Francisco to New Delhi

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 October 1, 2025.

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

    Istanbul airport offers the cheapest routes to Cairo, from $23; whereas Cheongju airport is typically cheaper if you're flying to Jeju City, from $24. 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 Istanbul to Ankara from $23 round trip
    Fly from Cheongju to Jeju City from $24 round trip
    Fly from Bogotá to Pereira from $30 round trip
    Fly from Bogotá to Medellín from $36 round trip
    Fly from Medellín to Cali from $36 round trip

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