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Kissimmee

$66+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MCO
Sep 2 — Sep 91
Tue 9/2
Tue 9/9
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 August 28, 2025.

Round-trip from

$144
(Priceline)

One-way from

$66
(CheapOair)

Popular in

April

Cheapest in

March

Average price

$240
From Westchester County to Kissimmee
Search Deals
One-way flight from Westchester County to Kissimmee
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Highest demand for flights based on searches. 0% potential increase in price ($1 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 August 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 August 28, 2025.

This Priceline deal was found by Cheapflights users on 8/27. 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 10/2712:10 pmHPN - MCO
1 stop4h 12mBreeze Airways
Thu 10/307:10 amMCO - HPN
1 stop4h 19mBreeze Airways
Deal found 8/27$144
This Expedia deal was found by Cheapflights users on 8/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:10 pmHPN - MCO
1 stop10h 59mBreeze Airways
Mon 11/37:20 amMCO - HPN
1 stop4h 08mBreeze Airways
Deal found 8/28$146
This JetBlue deal was found by Cheapflights users on 8/27. 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.
Fri 9/123:59 pmHPN - MCO
Nonstop2h 55mJetBlue
Sun 9/149:16 amMCO - HPN
Nonstop2h 43mJetBlue
Deal found 8/27$147
This Priceline deal was found by Cheapflights users on 8/27. 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 9/912:09 pmHPN - MCO
1 stop4h 16mBreeze Airways
Fri 9/127:20 amMCO - HPN
1 stop4h 08mBreeze Airways
Deal found 8/27$148
This CheapOair deal was found by Cheapflights users on 8/28. 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.
Mon 9/812:10 pmHPN - MCO
1 stop4h 12mBreeze Airways
Mon 9/157:20 amMCO - HPN
1 stop4h 08mBreeze Airways
Deal found 8/28$149
This Priceline deal was found by Cheapflights users on 8/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/912:09 pmHPN - MCO
1 stop4h 16mBreeze Airways
Mon 9/157:20 amMCO - HPN
1 stop4h 08mBreeze Airways
Deal found 8/28$150
This Breeze Airways deal was found by Cheapflights users on 8/27. 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.
Tue 9/1612:09 pmHPN - MCO
1 stop4h 16mBreeze Airways
Thu 9/187:10 amMCO - HPN
1 stop4h 19mBreeze Airways
Deal found 8/27$151
This Priceline deal was found by Cheapflights users on 8/27. 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 9/1512:10 pmHPN - MCO
1 stop4h 12mBreeze Airways
Mon 9/227:20 amMCO - HPN
1 stop4h 08mBreeze Airways
Deal found 8/27$152
This CheapOair deal was found by Cheapflights users on 8/25. 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 11/1012:10 pmHPN - MCO
1 stop4h 12mBreeze Airways
Thu 11/137:10 amMCO - HPN
1 stop4h 19mBreeze Airways
Deal found 8/25$153
This CheapOair deal was found by Cheapflights users on 8/26. 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 11/212:09 pmHPN - MCO
1 stop4h 16mBreeze Airways
Fri 11/77:20 amMCO - HPN
1 stop4h 08mBreeze Airways
Deal found 8/26$154
This Expedia deal was found by Cheapflights users on 8/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:10 pmHPN - MCO
1 stop10h 59mBreeze Airways
Wed 11/57:10 amMCO - HPN
1 stop5h 24mBreeze Airways
Deal found 8/26$155
This CheapOair deal was found by Cheapflights users on 8/26. 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 11/912:09 pmHPN - MCO
1 stop4h 16mBreeze Airways
Fri 11/147:20 amMCO - HPN
1 stop4h 08mBreeze Airways
Deal found 8/26$156

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 August 28, 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

Fri 10/31

12:10 pm-4:22 pm

1 stop4h 12m

Orlando

Mon 11/3

7:20 am-11:28 am

1 stop4h 08m

$144

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Fri 10/31

8:00 pm-10:45 pm

Nonstop2h 45m

Orlando

Tue 11/4

10:51 am-1:33 pm

Nonstop2h 42m

$147

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Sat 10/25

3:59 pm-6:51 pm

Nonstop2h 52m

Orlando

Sun 11/2

7:50 pm-10:34 pm

Nonstop2h 44m

$147

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Thu 9/11

3:59 pm-6:54 pm

Nonstop2h 55m

Orlando

Sun 9/14

9:16 am-11:59 am

Nonstop2h 43m

$147

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Fri 9/12

3:59 pm-6:54 pm

Nonstop2h 55m

Orlando

Sun 9/14

9:16 am-11:59 am

Nonstop2h 43m

$147

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Sun 10/5

7:59 pm-10:47 pm

Nonstop2h 48m

Orlando

Sat 10/11

9:16 am-11:57 am

Nonstop2h 41m

$147

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Tue 9/9

12:09 pm-4:25 pm

1 stop4h 16m

Orlando

Fri 9/12

7:20 am-11:28 am

1 stop4h 08m

$148

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Mon 9/8

12:10 pm-4:22 pm

1 stop4h 12m

Orlando

Mon 9/15

7:20 am-11:28 am

1 stop4h 08m

$149

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Mon 9/15

12:10 pm-4:22 pm

1 stop4h 12m

Orlando

Thu 9/18

7:10 am-11:29 am

1 stop4h 19m

$149

White PlainsOrlando

HPN - MCO

HPNMCO

White Plains Westchester County

Tue 9/9

12:09 pm-4:25 pm

1 stop4h 16m

Orlando

Mon 9/15

7:20 am-11:28 am

1 stop4h 08m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/26

Showing 1-10 of 17 results
1
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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, May is the cheapest month in which you can book a flight from Westchester County to Kissimmee (average of $206). Flying from Westchester County to Kissimmee in November is currently the most expensive (average of $289). 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 August 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Westchester County to Kissimmee as you normally would.

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 August 28, 2025.

The most flights from zzREU to K1S are scheduled on a Thursday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 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 August 28, 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
8.0
Very good
199 reviews

Crew

8.7

Boarding

8.2

Entertainment

6.6

Comfort

8.1

Overall

8.0

Food

6.7

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
8.0
Very good
199 reviews
Breeze Airways
8.0
Very good
199 reviews

Crew

8.7

Boarding

8.2

Entertainment

6.6

Comfort

8.1

Overall

8.0

Food

6.7

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
8.0
Very good
7,977 reviews
Breeze Airways
8.0
Very good
199 reviews

Crew

8.7

Boarding

8.2

Entertainment

6.6

Comfort

8.1

Overall

8.0

Food

6.7

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
10,000 reviews
Breeze Airways
8.0
Very good
199 reviews

Crew

8.7

Boarding

8.2

Entertainment

6.6

Comfort

8.1

Overall

8.0

Food

6.7

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
2,920 reviews
Breeze Airways
8.0
Very good
199 reviews

Crew

8.7

Boarding

8.2

Entertainment

6.6

Comfort

8.1

Overall

8.0

Food

6.7

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
3,204 reviews
Breeze Airways
8.0
Very good
199 reviews

Crew

8.7

Boarding

8.2

Entertainment

6.6

Comfort

8.1

Overall

8.0

Food

6.7

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!

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 Breeze Airways and JetBlue fly from Westchester County to Kissimmee in about 2h 45m. 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 flights from Westchester County to Kissimmee?

    The cheapest flight price from Westchester County to Kissimmee is $88. On average you can expect to pay $187. The most popular route, (White Plains Westchester County - Orlando), can usually be booked for $137.

  • 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, May is the cheapest month in which you can book a flight from Westchester County to Kissimmee (average of $206). Flying from Westchester County to Kissimmee in November is currently the most expensive (average of $289). 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 7 airlines flying from Westchester County to Kissimmee

Discover the top 7 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 August 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$29Average$105FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$51Average$108FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$97Average$244FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$103Average$250FlexibilityNo cancel feeOn-timeN/A
Avelo AirlinesCheapest$123Average$184FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$163Average$319FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$186Average$410FlexibilityNo cancel feeOn-time71%

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