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Kissimmee

$83+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MCO
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
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 January 15, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$153
(JetBlue)

One-way from

$83
(Super.com)

Popular in

April

Cheapest in

March

Average price

$162
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 ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 15, 2026.

This Priceline deal was found by Cheapflights users on 1/14. 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 2/212:08 pm
HPN
-
MCO
1 stop4h 20m
Breeze Airways
Wed 2/47:00 am
MCO
-
HPN
1 stop5h 47m
Breeze Airways
Deal found 1/14$153
This CheapOair deal was found by Cheapflights users on 1/15. 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 2/2012:08 pm
HPN
-
MCO
1 stop4h 20m
Breeze Airways
Thu 2/267:10 am
MCO
-
HPN
1 stop4h 18m
Breeze Airways
Deal found 1/15$154
This CheapOair deal was found by Cheapflights users on 1/15. 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.
Tue 1/2712:08 pm
HPN
-
MCO
1 stop4h 21m
Breeze Airways
Tue 2/107:10 am
MCO
-
HPN
1 stop4h 18m
Breeze Airways
Deal found 1/15$155
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 2/2012:08 pm
HPN
-
MCO
1 stop4h 20m
Multiple Airlines
Tue 2/246:36 pm
MCO
-
HPN
1 stop18h 11m
Multiple Airlines
Deal found 1/14$157
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
Tue 3/2412:08 pm
HPN
-
MCO
1 stop4h 21m
Breeze Airways
Mon 3/307:05 am
MCO
-
HPN
1 stop4h 23m
Breeze Airways
Deal found 1/15$158
This CheapOair deal was found by Cheapflights users on 1/15. 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.
Mon 1/2612:08 pm
HPN
-
MCO
1 stop4h 20m
Breeze Airways
Tue 2/37:10 am
MCO
-
HPN
1 stop4h 18m
Breeze Airways
Deal found 1/15$159
This Super.com deal was found by Cheapflights users on 1/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:08 pm
HPN
-
MCO
Nonstop4h 21m
Breeze Airways
Tue 3/37:10 am
MCO
-
HPN
Nonstop4h 18m
Breeze Airways
Deal found 1/13$160
This Priceline deal was found by Cheapflights users on 1/15. 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.
Tue 1/2712:08 pm
HPN
-
MCO
1 stop4h 21m
Multiple Airlines
Sat 1/318:20 pm
MCO
-
HPN
Nonstop2h 41m
Multiple Airlines
Deal found 1/15$161
This JetBlue deal was found by Cheapflights users on 1/15. 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 2/87:30 pm
HPN
-
MCO
Nonstop2h 57m
JetBlue
Sat 2/148:14 pm
MCO
-
HPN
Nonstop2h 43m
JetBlue
Deal found 1/15$162
This CheapOair deal was found by Cheapflights users on 1/15. 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.
Mon 1/2612:08 pm
HPN
-
MCO
1 stop4h 20m
Breeze Airways
Fri 2/67:05 am
MCO
-
HPN
1 stop4h 23m
Breeze Airways
Deal found 1/15$164
This Super.com deal was found by Cheapflights users on 1/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/317:30 pm
HPN
-
MCO
Nonstop2h 57m
JetBlue
Tue 2/33:48 pm
MCO
-
HPN
Nonstop2h 43m
JetBlue
Deal found 1/14$165

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 January 15, 2026.
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 2/21

7:30 pm-10:24 pm

Nonstop2h 54m

Orlando

Wed 2/25

6:44 pm-9:30 pm

Nonstop2h 46m

$153

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Thu 3/5

8:30 pm-11:22 pm

Nonstop2h 52m

Orlando

Sun 3/8

10:50 am-1:34 pm

Nonstop2h 44m

$177

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Thu 1/29

12:08 pm-4:29 pm

1 stop4h 21m

Orlando

Fri 1/30

7:05 am-11:28 am

1 stop4h 23m

$184

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Wed 6/17

4:05 pm-6:59 pm

Nonstop2h 54m

Orlando

Wed 6/24

5:00 pm-7:58 pm

Nonstop2h 58m

$187

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Sat 3/21

8:30 pm-11:22 pm

Nonstop2h 52m

Orlando

Thu 3/26

10:50 am-1:34 pm

Nonstop2h 44m

$197

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Tue 3/17

8:30 pm-11:22 pm

Nonstop2h 52m

Orlando

Wed 3/25

6:50 pm-9:36 pm

Nonstop2h 46m

$198

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Sun 2/8

12:08 pm-4:29 pm

1 stop4h 21m

Orlando

Sun 2/15

8:15 am-12:40 pm

1 stop4h 25m

$203

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Wed 4/8

3:13 pm-12:33 am

1 stop9h 20m

Orlando

Wed 4/22

7:00 am-12:00 pm

1 stop5h 00m

$207

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Mon 5/4

9:00 pm-11:41 pm

Nonstop2h 41m

Orlando

Wed 5/6

8:40 pm-11:30 pm

Nonstop2h 50m

$207

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Wed 3/25

8:30 pm-11:22 pm

Nonstop2h 52m

Orlando

Wed 4/1

8:55 pm-11:45 pm

Nonstop2h 50m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 23 results
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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 January 15, 2026.

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 41% 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 January 10, 2026.

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

Weekly flight availability from Westchester County to Kissimmee

Explore weekly flight availability from Westchester County to Kissimmee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 15, 2026.

The most flights from zzREU to K1S are scheduled on a Thursday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

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 January 15, 2026.
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
8.1
Very good
258 reviews

Crew

8.7

Entertainment

6.7

Overall

8.1

Food

6.7

Comfort

8.2

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.1
Very good
258 reviews
Breeze Airways
8.1
Very good
258 reviews

Crew

8.7

Entertainment

6.7

Overall

8.1

Food

6.7

Comfort

8.2

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Delta
7.9
Good
8,052 reviews
Breeze Airways
8.1
Very good
258 reviews

Crew

8.7

Entertainment

6.7

Overall

8.1

Food

6.7

Comfort

8.2

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,136 reviews
Breeze Airways
8.1
Very good
258 reviews

Crew

8.7

Entertainment

6.7

Overall

8.1

Food

6.7

Comfort

8.2

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
JetBlue
7.2
Good
2,887 reviews
Breeze Airways
8.1
Very good
258 reviews

Crew

8.7

Entertainment

6.7

Overall

8.1

Food

6.7

Comfort

8.2

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Frontier
5.7
Fair
3,057 reviews
Breeze Airways
8.1
Very good
258 reviews

Crew

8.7

Entertainment

6.7

Overall

8.1

Food

6.7

Comfort

8.2

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 Breeze Airways fly from Westchester County to Kissimmee in about 2h 54m. The time it takes to get you to your destination can typically vary by up to 1h 27m. The distance from Westchester County to Kissimmee is about 972 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Westchester County to Kissimmee one-way?

    $67 is the cheapest one-way deal found within the past few days, from Breeze Airways. You may also be able to find cheap deals on JetBlue and Delta, with prices starting from $88 and $89, respectively.

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

    The cheapest flight price from Westchester County to Kissimmee is $88. On average you can expect to pay $240. The most popular route, (White Plains Westchester County - Orlando), can usually be booked for $115.

  • 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$49Average$91FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$83Average$234FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$103Average$281FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$127Average$300FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$162Average$389FlexibilityNo cancel feeOn-time71%

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