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Kissimmee

$53+ Cheap flights from Westchester County to Kissimmee, FL

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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MCO
Dec 30 — Jan 61
Tue 12/30
Tue 1/6
1 adult, Economy
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Cheap flight deals from Westchester County to Kissimmee

Keep the following information in mind while searching for Westchester County to Kissimmee flight deals. Data was last updated November 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$180
(CheapOair)

One-way from

$53
(CheapOair)

Popular in

April

Cheapest in

September

Average price

$208
Provider with most accurate pricing for New York (NYC)-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Orlando (ORL) flights.
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From Westchester County to Kissimmee
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One-way flight from Westchester County to Kissimmee
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Highest demand for flights based on searches. 3% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Westchester County to Kissimmee

Cheapest flights from Westchester County to Kissimmee
Explore the most affordable flight options available from Westchester County to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 30, 2025.

This CheapOair deal was found by Cheapflights users on 11/28. 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 12/1212:10 pmHPN - MCO
1 stop4h 12mBreeze Airways
Mon 12/157:20 amMCO - HPN
1 stop4h 08mBreeze Airways
Deal found 11/28$180
This Breeze Airways deal was found by Cheapflights users on 11/29. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:10 pmHPN - MCO
1 stop4h 12mBreeze Airways
Wed 12/177:10 amMCO - HPN
1 stop5h 24mBreeze Airways
Deal found 11/29$181
This JetBlue deal was found by Cheapflights users on 11/28. 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 12/148:00 pmHPN - MCO
Nonstop2h 45mJetBlue
Sun 12/218:20 pmMCO - HPN
Nonstop2h 44mJetBlue
Deal found 11/28$182
This Breeze Airways deal was found by Cheapflights users on 11/29. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/412:09 pmHPN - MCO
1 stop4h 16mBreeze Airways
Thu 12/117:10 amMCO - HPN
1 stop4h 19mBreeze Airways
Deal found 11/29$184
This CheapOair deal was found by Cheapflights users on 11/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:10 pmHPN - MCO
1 stop4h 12mBreeze Airways
Sun 12/147:10 amMCO - HPN
1 stop4h 19mBreeze Airways
Deal found 11/29$186
This American Airlines deal was found by Cheapflights users on 11/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:04 amHPN - MCO
1 stop6h 57mAmerican Airlines
Thu 1/15:00 amMCO - HPN
1 stop4h 29mAmerican Airlines
Deal found 11/29$188
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 12/128:00 amHPN - MCO
2 stops26h 32mBreeze Airways
Thu 1/227:10 amMCO - HPN
1 stop4h 18mBreeze Airways
Deal found 11/28$189
This Kiwi.com deal was found by Cheapflights users on 11/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/812:10 pmHPN - MCO
1 stop4h 12mMultiple Airlines
Mon 12/158:25 pmMCO - HPN
2 stops40h 09mMultiple Airlines
Deal found 11/29$190
This CheapOair deal was found by Cheapflights users on 11/28. 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 12/1412:09 pmHPN - MCO
1 stop4h 16mBreeze Airways
Mon 12/157:20 amMCO - HPN
1 stop4h 08mBreeze Airways
Deal found 11/28$195
This Delta deal was found by Cheapflights users on 11/28. 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.
Mon 12/153:08 pmHPN - MCO
1 stop9h 00mDelta
Wed 12/244:20 pmMCO - HPN
1 stop5h 49mDelta
Deal found 11/28$197

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Kissimmee 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 November 30, 2025.
Use the filters below to find and compare flights from Westchester County to Kissimmee that are best for you.

Fly from

Westchester County

Fly to

Kissimmee

Route

Depart

Return

Price

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Sat 1/24

7:30 pm-10:27 pm

Nonstop2h 57m

Orlando

Sat 1/31

8:20 pm-11:01 pm

Nonstop2h 41m

$187

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Sat 1/24

3:10 pm-12:18 am

1 stop9h 08m

Orlando

Wed 1/28

6:00 am-11:56 am

1 stop5h 56m

$197

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Sat 2/21

9:00 pm-11:52 pm

Nonstop2h 52m

Orlando

Wed 2/25

4:05 pm-6:50 pm

Nonstop2h 45m

$207

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Sat 2/21

5:12 pm-11:04 pm

1 stop5h 52m

Orlando

Wed 2/25

7:00 am-12:06 pm

1 stop5h 06m

$207

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Mon 2/16

7:30 pm-10:24 pm

Nonstop2h 54m

Orlando

Wed 2/18

7:14 pm-10:00 pm

Nonstop2h 46m

$207

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Tue 2/10

2:59 pm-5:56 pm

Nonstop2h 57m

Orlando

Wed 2/18

7:14 pm-10:00 pm

Nonstop2h 46m

$207

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Sun 12/7

12:09 pm-4:25 pm

1 stop4h 16m

Orlando

Wed 12/10

7:10 am-12:34 pm

1 stop5h 24m

$223

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Wed 12/31

9:20 pm-12:11 am

Nonstop2h 51m

Orlando

Thu 1/1

8:20 pm-11:04 pm

Nonstop2h 44m

$224

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Fri 12/5

12:10 pm-4:22 pm

1 stop4h 12m

Orlando

Sun 12/7

7:10 am-11:29 am

1 stop4h 19m

$228

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Tue 1/27

12:08 pm-4:29 pm

1 stop4h 21m

$55

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/28

Showing 1-10 of 20 results
1
2

Best time to book a flight from Westchester County to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee 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.

Cheapflights Insights

Everything you need to know about your flight from Westchester County to Kissimmee

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

Currently, October is the cheapest month in which you can book a flight from Westchester County to Kissimmee (average of $91). Flying from Westchester County to Kissimmee in May is currently the most expensive (average of $197). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from REU to K1S?

Find hourly flight availability from Westchester County to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Westchester County to Kissimmee in the afternoon. If you’re flexible enough to do this you can expect to save up to 28% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Westchester County to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Westchester County to Kissimmee. Price data was last updated on November 25, 2025.

Travelers seeking maximum savings on their Westchester County to Kissimmee flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Kissimmee

Get insights into the airlines that provide service to Kissimmee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kissimmee. Reviews last updated November 30, 2025.
See what other customers who have flown with Breeze Airways, Delta, and American Airlines from Westchester County to Kissimmee have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
240 reviews

Entertainment

6.6

Crew

8.7

Food

6.7

Overall

8.2

Boarding

8.3

Comfort

8.2

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!
Breeze Airways
8.2
Very good
240 reviews
Breeze Airways
8.2
Very good
240 reviews

Entertainment

6.6

Crew

8.7

Food

6.7

Overall

8.2

Boarding

8.3

Comfort

8.2

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!
Delta
7.9
Good
8,010 reviews
Breeze Airways
8.2
Very good
240 reviews

Entertainment

6.6

Crew

8.7

Food

6.7

Overall

8.2

Boarding

8.3

Comfort

8.2

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!
American Airlines
7.2
Good
11,042 reviews
Breeze Airways
8.2
Very good
240 reviews

Entertainment

6.6

Crew

8.7

Food

6.7

Overall

8.2

Boarding

8.3

Comfort

8.2

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!
JetBlue
7.2
Good
2,904 reviews
Breeze Airways
8.2
Very good
240 reviews

Entertainment

6.6

Crew

8.7

Food

6.7

Overall

8.2

Boarding

8.3

Comfort

8.2

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!
Frontier
5.8
Fair
3,099 reviews
Breeze Airways
8.2
Very good
240 reviews

Entertainment

6.6

Crew

8.7

Food

6.7

Overall

8.2

Boarding

8.3

Comfort

8.2

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Kissimmee. 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 Westchester County to Kissimmee?

    Airlines like JetBlue and Delta fly from Westchester County to Kissimmee in about 2h 57m. The time it takes to get you to your destination can typically vary by up to 6h 11m. The distance from Westchester County to Kissimmee is about 972 mi. This flight may include one or multiple stops.

  • What are the cheapest flights from Westchester County to Kissimmee?

    The cheapest flight price from Westchester County to Kissimmee is $93. On average you can expect to pay $286. The most popular route, (White Plains Westchester County - Orlando), can usually be booked for $103.

  • Can I find deals for flights from Westchester County to Kissimmee that include hotel bookings?

    Yes. In addition to deals on Westchester County to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Kissimmee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Westchester County to Kissimmee.

  • Can I find deals for business class flights from Westchester County to Kissimmee?

    Yes. Cheapflights offers flight deals from Westchester County to Kissimmee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, October is the cheapest month in which you can book a flight from Westchester County to Kissimmee (average of $91). Flying from Westchester County to Kissimmee in May is currently the most expensive (average of $197). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Westchester County to Kissimmee

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Top 5 airlines flying from Westchester County to Kissimmee

Discover the top 5 airlines that operate flights from Westchester County to Kissimmee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$29Average$109FlexibilityNo cancel feeOn-time62%
DeltaCheapest$103Average$282FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$105Average$240FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$130Average$305FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$176Average$403FlexibilityNo cancel feeOn-time71%

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