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Kissimmee

$45+ Cheap flights from Kentucky 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MCO
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Kentucky to Kissimmee

Keep the following information in mind while searching for Kentucky to Kissimmee flight deals. Data was last updated January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$89
(Cheapflightsfares)

One-way from

$45
(Booking.com)

Popular in

December

Cheapest in

September

Average price

$256
Provider with most accurate pricing for Louisville Intl-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-Orlando (ORL) flights.
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From Kentucky to Kissimmee
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One-way flight from Kentucky to Kissimmee
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Highest demand for flights based on searches. 18% potential increase in price ($53 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 January 2026
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Find flight deals from Kentucky to Kissimmee

Cheapest flights from Kentucky to Kissimmee
Explore the most affordable flight options available from Kentucky to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/110:30 am
CVG
-
MCO
Nonstop2h 21m
Frontier
Sat 2/77:52 pm
MCO
-
CVG
Nonstop2h 28m
Frontier
Deal found 1/14$89
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/157:14 pm
CVG
-
MCO
Nonstop2h 19m
Frontier
Fri 2/2010:38 pm
MCO
-
CVG
Nonstop2h 21m
Frontier
Deal found 1/14$90
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/275:50 pm
BNA
-
MCO
Nonstop1h 58m
Spirit Airlines
Sat 1/313:44 pm
MCO
-
BNA
Nonstop2h 11m
Spirit Airlines
Deal found 1/14$93
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:04 pm
CVG
-
MCO
1 stop5h 21m
Frontier
Wed 3/46:54 pm
MCO
-
CVG
Nonstop2h 31m
Frontier
Deal found 1/14$93
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.
Mon 2/2310:50 am
BNA
-
MCO
Nonstop1h 59m
Frontier
Thu 2/266:55 am
MCO
-
BNA
Nonstop2h 20m
Frontier
Deal found 1/13$94
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:45 am
CVG
-
MCO
Nonstop2h 22m
Frontier
Sun 3/1510:20 pm
MCO
-
CVG
Nonstop2h 21m
Frontier
Deal found 1/13$94
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:25 am
BNA
-
MCO
Nonstop1h 55m
Spirit Airlines
Tue 2/247:20 am
MCO
-
BNA
Nonstop2h 09m
Spirit Airlines
Deal found 1/13$95
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:45 am
CVG
-
MCO
Nonstop2h 21m
Frontier
Tue 3/175:01 am
MCO
-
CVG
Nonstop2h 22m
Frontier
Deal found 1/14$95
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:25 am
BNA
-
MCO
Nonstop1h 55m
Spirit Airlines
Sat 2/281:53 pm
MCO
-
BNA
Nonstop2h 10m
Spirit Airlines
Deal found 1/14$96
This WAYA 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/118:40 am
BNA
-
MCO
1 stop4h 32m
Spirit Airlines
Sun 2/157:20 am
MCO
-
BNA
Nonstop2h 09m
Spirit Airlines
Deal found 1/14$97
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/810:00 am
CVG
-
MCO
Nonstop2h 21m
Frontier
Sat 3/1410:20 pm
MCO
-
CVG
Nonstop2h 21m
Frontier
Deal found 1/14$97
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.
Sat 2/213:59 pm
BNA
-
MCO
Nonstop1h 56m
Spirit Airlines
Mon 3/26:45 pm
MCO
-
BNA
Nonstop2h 12m
Spirit Airlines
Deal found 1/13$98

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky 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 Kentucky to Kissimmee that are best for you.

Fly from

Kentucky

Fly to

Kissimmee

Route

Depart

Return

Price

BlountvilleOrlando

TRI - MCO

TRIMCO

Blountville Tri Cities TN/VA

Mon 3/16

5:08 pm-7:03 pm

Nonstop1h 55m

Orlando

Mon 3/23

10:18 am-12:13 pm

Nonstop1h 55m

$97

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Mon 3/16

7:46 pm-10:57 pm

Nonstop2h 11m

Orlando

Mon 3/23

5:34 pm-7:06 pm

Nonstop2h 32m

$103

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Fri 1/30

7:46 pm-10:57 pm

Nonstop2h 11m

Orlando

Fri 2/6

5:34 pm-7:06 pm

Nonstop2h 32m

$103

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Mon 2/23

7:46 pm-10:57 pm

Nonstop2h 11m

Orlando

Fri 2/27

5:34 pm-7:06 pm

Nonstop2h 32m

$107

CincinnatiOrlando

CVG - MCO

CVGMCO

Cincinnati Cinci./N. Kentucky

Fri 3/6

5:45 am-8:07 am

Nonstop2h 22m

Orlando

Fri 3/13

11:16 am-1:45 pm

Nonstop2h 29m

$127

BlountvilleOrlando

TRI - MCO

TRIMCO

Blountville Tri Cities TN/VA

Mon 2/9

5:08 pm-7:03 pm

Nonstop1h 55m

Orlando

Fri 2/13

5:01 am-4:28 pm

1 stop11h 27m

$131

BlountvilleOrlando

TRI - MCO

TRIMCO

Blountville Tri Cities TN/VA

Mon 1/26

5:08 pm-7:03 pm

Nonstop1h 55m

Orlando

Mon 2/9

10:18 am-12:13 pm

Nonstop1h 55m

$132

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Fri 3/13

7:46 pm-10:57 pm

Nonstop2h 11m

Orlando

Mon 3/16

5:34 pm-7:06 pm

Nonstop2h 32m

$158

CincinnatiOrlando

CVG - MCO

CVGMCO

Cincinnati Cinci./N. Kentucky

Mon 2/9

4:50 pm-7:00 pm

Nonstop2h 10m

Orlando

Wed 2/18

1:15 pm-7:40 pm

1 stop6h 25m

$159

BlountvilleOrlando

TRI - MCO

TRIMCO

Blountville Tri Cities TN/VA

Fri 2/27

12:53 pm-6:55 am

2 stops18h 02m

Orlando

Mon 3/2

10:18 am-12:13 pm

Nonstop1h 55m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Kissimmee

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

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

Currently, August is the cheapest month in which you can book a flight from Kentucky to Kissimmee (average of $52). Flying from Kentucky to Kissimmee in October is currently the most expensive (average of $99). 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 KY to K1S?

Find hourly flight availability from Kentucky 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 Kentucky to Kissimmee at noon. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Kentucky to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Kissimmee. Price data was last updated on September 28, 2025.

Travelers seeking maximum savings on their Kentucky to Kissimmee flight should consider departing on Thursday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Kentucky 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 Kentucky to Kissimmee?

    A quick flight from Kentucky to Kissimmee can take about 1h 55m. Breeze Airways provides one of the quickest options available for as low as $97. The distance between Kentucky and Kissimmee is about 559 mi. Generally, flights for this route are nonstop.

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

    $19 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Allegiant Air, with prices starting from $45 and $52, respectively.

  • What are the most popular routes from Kentucky to Kissimmee?

    The most popular route from Kentucky to Kissimmee is Cincinnati Cinci./N. Kentucky - Orlando. You may also consider Nashville Intl - Orlando or Lexington Blue Grass - Orlando.

  • What are the most reliable airlines from Kentucky to Kissimmee?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Kentucky to Kissimmee on time: Southwest (80%), KLM (55%), Delta (55%).

  • What are the cheapest flights from Kentucky to Kissimmee?

    The cheapest flight price from Kentucky to Kissimmee is $70. On average you can expect to pay $242. The most popular route, (Cincinnati Cinci./N. Kentucky - Orlando), can usually be booked for $78.

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

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

  • How can I find direct flights from Kentucky to Kissimmee?

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

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

    Yes. Cheapflights offers flight deals from Kentucky 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 Kentucky to Kissimmee?

    Currently, August is the cheapest month in which you can book a flight from Kentucky to Kissimmee (average of $52). Flying from Kentucky to Kissimmee in October is currently the most expensive (average of $99). 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 Kentucky to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Kentucky to Kissimmee

Discover the top 8 airlines that operate flights from Kentucky 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
Spirit AirlinesCheapest$56Average$143FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$66Average$163FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$72Average$163FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$78Average$178FlexibilityNo cancel feeOn-time88%
DeltaCheapest$124Average$356FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$150Average$336FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$181Average$392FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$199Average$381FlexibilityNo cancel feeOn-time63%

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