HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kissimmee

$39+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MCO
Jun 28 — Jul 51
Sun 6/28
Sun 7/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kentucky to Kissimmee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 May 29, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 5/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/267:22 pm
TYS
-
MCO
Nonstop1h 36m
Allegiant Air
Fri 7/39:48 pm
MCO
-
TYS
Nonstop1h 45m
Allegiant Air
Deal found 5/27$97
This Kiwi.com deal was found by Cheapflights users on 5/29. 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.
Fri 8/76:29 pm
TYS
-
MCO
Nonstop1h 38m
Allegiant Air
Fri 8/148:57 pm
MCO
-
TYS
Nonstop1h 47m
Allegiant Air
Deal found 5/29$98
This Super.com deal was found by Cheapflights users on 5/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:24 pm
TYS
-
MCO
Nonstop1h 36m
Allegiant Air
Mon 6/299:48 pm
MCO
-
TYS
Nonstop1h 46m
Allegiant Air
Deal found 5/25$102
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 8/285:05 pm
BNA
-
MCO
Nonstop2h 05m
Frontier
Mon 8/313:04 pm
MCO
-
BNA
Nonstop2h 16m
Frontier
Deal found 5/24$103
This Frontier deal was found by Cheapflights users on 5/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2711:12 am
BNA
-
MCO
Nonstop2h 13m
Frontier
Mon 8/32:49 pm
MCO
-
BNA
Nonstop2h 16m
Frontier
Deal found 5/27$105
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/35:05 pm
BNA
-
MCO
Nonstop2h 14m
Frontier
Mon 8/172:49 pm
MCO
-
BNA
Nonstop2h 16m
Frontier
Deal found 5/24$107
This Super.com deal was found by Cheapflights users on 5/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:05 pm
BNA
-
MCO
Nonstop2h 14m
Frontier
Fri 7/179:05 am
MCO
-
BNA
Nonstop2h 12m
Frontier
Deal found 5/28$108
This Kiwi.com deal was found by Cheapflights users on 5/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:10 pm
TRI
-
MCO
Nonstop1h 55m
Breeze Airways
Fri 8/287:20 am
MCO
-
TRI
Nonstop1h 55m
Breeze Airways
Deal found 5/25$108
This Cheapflightsfares deal was found by Cheapflights users on 5/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:20 pm
TYS
-
MCO
Nonstop1h 38m
Allegiant Air
Mon 7/209:48 pm
MCO
-
TYS
Nonstop1h 45m
Allegiant Air
Deal found 5/27$109
This Frontier deal was found by Cheapflights users on 5/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:05 pm
BNA
-
MCO
Nonstop2h 14m
Frontier
Fri 7/179:05 am
MCO
-
BNA
Nonstop2h 12m
Frontier
Deal found 5/28$109
This Super.com deal was found by Cheapflights users on 5/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:09 pm
BNA
-
MCO
Nonstop2h 05m
Frontier
Mon 7/62:49 pm
MCO
-
BNA
Nonstop2h 16m
Frontier
Deal found 5/25$112
This Kiwi.com deal was found by Cheapflights users on 5/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:02 pm
TRI
-
MCO
Nonstop1h 55m
Breeze Airways
Fri 6/1210:12 am
MCO
-
TRI
Nonstop1h 55m
Breeze Airways
Deal found 5/25$112

Find flight deals from Kentucky to Kissimmee

Keep the following information in mind while searching for Kentucky to Kissimmee flight deals. Data was last updated May 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Cheapflightsfares)

One-way from

$39
(Kiwi.com)

Popular in

April

Cheapest in

July

Average price

$261
Provider with most accurate pricing for Louisville Intl-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Orlando (ORL) flights.
Search Deals
From Kentucky to Kissimmee
Search Deals
One-way flight from Kentucky to Kissimmee
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 29, 2026.
Use the filters below to find and compare flights from Kentucky to Kissimmee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BlountvilleOrlando

TRI - MCO

TRIMCO

Blountville Tri Cities TN/VA

Mon 6/8

5:02 pm-6:57 pm

Nonstop1h 55m

Orlando

Fri 6/12

10:12 am-12:07 pm

Nonstop1h 55m

$118

BlountvilleOrlando

TRI - MCO

TRIMCO

Blountville Tri Cities TN/VA

Mon 6/22

5:02 pm-6:57 pm

Nonstop1h 55m

Orlando

Fri 6/26

10:12 am-12:07 pm

Nonstop1h 55m

$118

BlountvilleOrlando

TRI - MCO

TRIMCO

Blountville Tri Cities TN/VA

Fri 7/3

2:10 pm-4:05 pm

Nonstop1h 55m

Orlando

Mon 7/13

7:20 am-9:15 am

Nonstop1h 55m

$138

KnoxvilleOrlando

TYS - MCO

TYSMCO

Knoxville McGhee Tyson

Tue 7/7

12:45 pm-2:25 pm

Nonstop1h 40m

Orlando

Wed 7/15

4:15 pm-9:20 pm

1 stop5h 05m

$213

NashvilleOrlando

BNA - MCO

BNAMCO

Nashville Intl

Tue 9/22

10:10 am-2:35 pm

1 stop3h 25m

Orlando

Tue 9/29

2:35 pm-5:50 pm

1 stop4h 15m

$224

KnoxvilleOrlando

TYS - MCO

TYSMCO

Knoxville McGhee Tyson

Wed 7/1

5:40 am-8:55 am

1 stop3h 15m

Orlando

Wed 7/8

10:05 am-2:48 pm

1 stop4h 43m

$225

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Sat 7/4

6:22 am-12:00 pm

1 stop4h 38m

Orlando

Wed 7/8

10:05 am-1:02 pm

1 stop3h 57m

$237

CincinnatiOrlando

CVG - MCO

CVGMCO

Cincinnati Cinci./N. Kentucky

Sat 8/1

7:45 pm-1:01 am

1 stop5h 16m

Orlando

Sun 8/9

7:09 am-1:00 pm

1 stop5h 51m

$239

CincinnatiOrlando

CVG - MCO

CVGMCO

Cincinnati Cinci./N. Kentucky

Sat 7/25

7:45 pm-1:01 am

1 stop5h 16m

Orlando

Wed 7/29

10:52 am-4:49 pm

1 stop5h 57m

$239

CincinnatiOrlando

CVG - MCO

CVGMCO

Cincinnati Cinci./N. Kentucky

Tue 6/30

1:31 pm-7:04 pm

1 stop5h 33m

Orlando

Tue 7/7

5:30 am-11:25 am

1 stop5h 55m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/27

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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 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 May 29, 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 24% on your trip compared to booking a flight in the morning.

How much does it cost to fly round-trip from Kentucky to Kissimmee?

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 May 23, 2026.

Travelers seeking maximum savings on their Kentucky to Kissimmee flight should consider departing on Wednesday evenings when fares are most often at their lowest. Friday afternoons 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 40m. Breeze Airways provides one of the quickest options available for as low as $213. The distance between Kentucky and Kissimmee is about 533 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $47 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Allegiant Air, with prices starting from $48 and $54, 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 Louisville Intl - 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: Delta (100%), Republic Airways (100%), Southwest (79%).

  • What are the cheapest flights from Kentucky to Kissimmee?

    The cheapest flight price from Kentucky to Kissimmee is $167. On average you can expect to pay $352. The most popular route, (Cincinnati Cinci./N. Kentucky - Orlando), can usually be booked for $136.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Kentucky to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Miami flights
Newark to Orlando flights
LaGuardia to Miami flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
LaGuardia to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
LaGuardia to Fort Lauderdale flights
O'Hare Intl to Orlando flights
Newark to Tampa flights
Philadelphia to Orlando flights
Dallas/Fort Worth to Orlando flights
Boston to Orlando flights
Dallas/Fort Worth to Miami flights
Dulles Intl to Miami flights
Hobby to Orlando flights
John F Kennedy Intl to West Palm Beach flights
Newark to West Palm Beach flights
Atlanta to Miami flights
O'Hare Intl to Miami flights
Philadelphia to Miami flights
Philadelphia to Fort Lauderdale flights
Los Angeles to Miami flights
Hobby to Miami flights
John F Kennedy Intl to Tampa flights
LaGuardia to Tampa flights
Dulles Intl to Orlando flights
Boston to Miami flights
Dallas/Fort Worth to Fort Lauderdale flights
Reagan-National to Miami flights
Baltimore to Orlando flights
Dulles Intl to Tampa flights
O'Hare Intl to Tampa flights
Boston to Fort Lauderdale flights
Los Angeles to Orlando flights
George Bush Intcntl to Miami flights
Baltimore to Tampa flights
Detroit to Orlando flights
Baltimore to Miami flights
O'Hare Intl to Fort Lauderdale flights
Reagan-National to Orlando flights
George Bush Intcntl to Orlando flights
Boston to Tampa flights
Cleveland to Orlando flights
Atlanta to Fort Lauderdale flights
Dallas/Fort Worth to Tampa flights
Dulles Intl to Fort Lauderdale flights
Los Angeles to Fort Lauderdale flights
Philadelphia to Tampa flights

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 May 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$40Average$143FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$64Average$168FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$79Average$185FlexibilityNo cancel feeOn-time88%
FrontierCheapest$89Average$192FlexibilityNo cancel feeOn-time62%
DeltaCheapest$148Average$422FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$150Average$347FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$178Average$402FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$387FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.