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Kissimmee

$219+ Cheap flights from Owensboro (OWB) to Kissimmee, FL

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
OWB — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Owensboro to Kissimmee

Cheapest flights from Owensboro to Kissimmee
Explore the most affordable flight options available from Owensboro to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/272:15 pm
OWB
-
MCO
1 stop27h 23m
Multiple Airlines
Wed 3/411:56 am
MCO
-
OWB
1 stop7h 54m
Multiple Airlines
Deal found 1/28$219
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Sat 2/281:55 pm
OWB
-
MCO
2 stops16h 44m
Multiple Airlines
Sat 3/79:23 pm
MCO
-
OWB
1 stop15h 07m
Multiple Airlines
Deal found 1/29$241
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/202:15 pm
OWB
-
MCO
1 stop8h 12m
Multiple Airlines
Mon 3/231:14 pm
MCO
-
OWB
1 stop6h 36m
Multiple Airlines
Deal found 1/27$289
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 3/258:35 am
OWB
-
MCO
1 stop6h 49m
Multiple Airlines
Sun 3/297:33 am
MCO
-
OWB
1 stop12h 17m
Multiple Airlines
Deal found 1/28$294
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/118:40 am
OWB
-
MCO
1 stop6h 51m
Multiple Airlines
Sun 2/155:15 am
MCO
-
OWB
2 stops14h 45m
Multiple Airlines
Deal found 1/27$388

Find flight deals from Owensboro to Kissimmee

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

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$219
(Kiwi.com)
Provider with most accurate pricing for Owensboro Daviess County-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Owensboro Daviess County-Orlando (ORL) flights.
Search Deals
From Owensboro Daviess County to Kissimmee
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Owensboro 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 29, 2026.
Use the filters below to find and compare flights from Owensboro to Kissimmee that are best for you.

Fly from

Owensboro

Fly to

Kissimmee

Route

Depart

Return

Price

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Fri 2/27

2:15 pm-6:38 pm

1 stop27h 23m

Orlando

Wed 3/4

11:56 am-6:50 pm

1 stop7h 54m

$219

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Fri 3/20

2:15 pm-11:27 pm

1 stop8h 12m

Orlando

Mon 3/23

1:14 pm-6:50 pm

1 stop6h 36m

$289

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Wed 3/25

8:35 am-4:24 pm

1 stop6h 49m

Orlando

Sun 3/29

7:33 am-6:50 pm

1 stop12h 17m

$294

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Wed 2/11

8:40 am-1:49 pm

3 stops28h 09m

Orlando

Sun 2/15

5:23 pm-12:25 pm

2 stops20h 02m

$405

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Fri 2/13

3:10 pm-2:34 pm

1 stop22h 24m

Orlando

Sat 2/21

11:05 pm-12:25 pm

2 stops38h 20m

$845

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Best time to book a flight from Owensboro to Kissimmee

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

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

Currently, August is the cheapest month in which you can book a flight from Owensboro to Kissimmee (average of $52). Flying from Owensboro 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.

Related info for your journey

Find useful and relevant information for your journey from Owensboro to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Owensboro to Kissimmee?

    Located just 3.6 mi from the city center, Owensboro Daviess County is the airport most travelers will use when flying to Kissimmee from Owensboro. Booking flights from Daviess County (OWB) to Kissimmee should be relatively easy as there are 0 daily outbound flights to Kissimmee from 0 different airlines.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Owensboro to Kissimmee (average of $52). Flying from Owensboro 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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