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Westchester County

$31+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MCO
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 November 13, 2025.

This Priceline deal was found by Cheapflights users on 11/11. 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 1/71:17 pmHPN - MSY
1 stop4h 56mBreeze Airways
Sun 1/117:00 amMSY - HPN
1 stop4h 40mBreeze Airways
Deal found 11/11$117
This Breeze Airways deal was found by Cheapflights users on 11/11. 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.
Fri 1/98:00 amHPN - CHS
Nonstop2h 13mBreeze Airways
Mon 1/126:49 pmCHS - HPN
Nonstop2h 10mBreeze Airways
Deal found 11/11$118
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/121:20 pmHPN - MSY
1 stop4h 51mBreeze Airways
Sun 12/147:00 amMSY - HPN
1 stop4h 39mBreeze Airways
Deal found 11/12$118
This Priceline deal was found by Cheapflights users on 11/12. 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.
Fri 1/238:00 amHPN - CHS
Nonstop2h 13mBreeze Airways
Mon 1/266:49 pmCHS - HPN
Nonstop2h 10mBreeze Airways
Deal found 11/12$122
This Priceline deal was found by Cheapflights users on 11/11. 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 12/101:14 pmHPN - MSY
1 stop4h 51mBreeze Airways
Sun 12/147:00 amMSY - HPN
1 stop4h 39mBreeze Airways
Deal found 11/11$122
This Priceline deal was found by Cheapflights users on 11/11. 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.
Thu 1/81:20 pmHPN - MSY
1 stop4h 56mBreeze Airways
Sun 1/117:00 amMSY - HPN
1 stop4h 40mBreeze Airways
Deal found 11/11$123
This CheapOair deal was found by Cheapflights users on 11/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/81:20 pmHPN - MSY
1 stop4h 56mBreeze Airways
Thu 1/157:00 amMSY - HPN
1 stop4h 40mBreeze Airways
Deal found 11/11$126
This JetBlue deal was found by Cheapflights users on 11/10. 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 1/177:00 amHPN - TPA
Nonstop2h 55mJetBlue
Sat 1/248:00 amTPA - HPN
Nonstop2h 50mJetBlue
Deal found 11/10$127
This CheapOair deal was found by Cheapflights users on 11/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/68:00 amHPN - CHS
Nonstop2h 13mBreeze Airways
Sun 2/89:13 amCHS - HPN
Nonstop2h 10mBreeze Airways
Deal found 11/12$127
This CheapOair deal was found by Cheapflights users on 11/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/111:19 pmHPN - MSY
1 stop4h 55mBreeze Airways
Sun 12/147:00 amMSY - HPN
1 stop4h 39mBreeze Airways
Deal found 11/12$127
This CheapOair deal was found by Cheapflights users on 11/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/101:14 pmHPN - MSY
1 stop4h 51mBreeze Airways
Wed 12/177:10 amMSY - HPN
1 stop4h 24mBreeze Airways
Deal found 11/12$128
This CheapOair deal was found by Cheapflights users on 11/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1112:03 pmHPN - CHS
Nonstop2h 13mBreeze Airways
Thu 1/159:13 amCHS - HPN
Nonstop2h 10mBreeze Airways
Deal found 11/11$132

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 November 13, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Orlando

Route

Depart

Return

Price

White PlainsCharleston

HPN - CHS

HPNCHS

White Plains Westchester County

Fri 1/9

8:00 am-10:13 am

Nonstop2h 13m

Charleston

Mon 1/12

6:49 pm-8:59 pm

Nonstop2h 10m

$118

White PlainsCharleston

HPN - CHS

HPNCHS

White Plains Westchester County

Thu 1/22

12:03 pm-2:16 pm

Nonstop2h 13m

Charleston

Fri 1/23

6:49 pm-8:59 pm

Nonstop2h 10m

$118

White PlainsTampa

HPN - TPA

HPNTPA

White Plains Westchester County

Mon 1/19

7:00 am-9:55 am

Nonstop2h 55m

Tampa

Thu 1/22

8:00 am-10:50 am

Nonstop2h 50m

$127

White PlainsTampa

HPN - TPA

HPNTPA

White Plains Westchester County

Tue 1/13

7:00 am-9:55 am

Nonstop2h 55m

Tampa

Mon 1/26

8:00 am-10:50 am

Nonstop2h 50m

$127

White PlainsTampa

HPN - TPA

HPNTPA

White Plains Westchester County

Tue 1/13

7:00 am-9:55 am

Nonstop2h 55m

Tampa

Sat 1/24

8:00 am-10:50 am

Nonstop2h 50m

$127

White PlainsCharleston

HPN - CHS

HPNCHS

White Plains Westchester County

Fri 2/6

8:00 am-10:13 am

Nonstop2h 13m

Charleston

Sun 2/8

9:13 am-11:23 am

Nonstop2h 10m

$127

White PlainsNew Orleans

HPN - MSY

HPNMSY

White Plains Westchester County

Thu 1/22

1:20 pm-5:16 pm

1 stop4h 56m

New Orleans Louis Armstrong

Sun 1/25

7:00 am-12:40 pm

1 stop4h 40m

$136

White PlainsNew Orleans

HPN - MSY

HPNMSY

White Plains Westchester County

Thu 1/22

1:20 pm-5:16 pm

1 stop4h 56m

New Orleans Louis Armstrong

Mon 1/26

7:03 am-12:30 pm

1 stop4h 27m

$136

White PlainsCharleston

HPN - CHS

HPNCHS

White Plains Westchester County

Sat 12/6

1:29 pm-3:39 pm

Nonstop2h 10m

Charleston

Tue 12/9

9:17 am-11:29 am

Nonstop2h 12m

$143

White PlainsNew Orleans

HPN - MSY

HPNMSY

White Plains Westchester County

Mon 2/2

12:08 pm-5:52 pm

1 stop6h 44m

New Orleans Louis Armstrong

Sun 2/8

7:00 am-12:40 pm

1 stop4h 40m

$146

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

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 $91). 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 November 2, 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 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, American Airlines, Breeze Airways, Delta, Frontier. These airlines depart to the following popular destinations: Orlando.

JetBlue
JetBlue
From $73
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 November 13, 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 Breeze Airways, Delta, 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.
Breeze Airways
8.1
Very good
230 reviews

Crew

8.7

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.1
Very good
230 reviews
Breeze Airways
8.1
Very good
230 reviews

Crew

8.7

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Delta
7.9
Good
8,008 reviews
Breeze Airways
8.1
Very good
230 reviews

Crew

8.7

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
11,050 reviews
Breeze Airways
8.1
Very good
230 reviews

Crew

8.7

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
JetBlue
7.2
Good
2,907 reviews
Breeze Airways
8.1
Very good
230 reviews

Crew

8.7

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Frontier
5.8
Fair
3,111 reviews
Breeze Airways
8.1
Very good
230 reviews

Crew

8.7

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.1

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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Popular international destinations from United States

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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 November 13, 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 Medellín from $28 round trip
    Fly from Medellín to Bogotá from $29 round trip
    Fly from Venice to Tirana from $30 round trip

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