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Kissimmee

$310+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
OWB — MCO
Aug 25 — Sep 11
Tue 8/25
Tue 9/1
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 July 26, 2026.

This United Airlines deal was found by Cheapflights users on 7/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:45 am
OWB
-
MCO
1 stop7h 55m
United Airlines
Sat 11/149:00 am
MCO
-
OWB
1 stop5h 40m
United Airlines
Deal found 7/23$310
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Sat 8/299:00 am
OWB
-
MCO
1 stop12h 11m
Multiple Airlines
Sun 8/306:10 am
MCO
-
OWB
1 stop14h 10m
Multiple Airlines
Deal found 7/24$343
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Tue 9/19:00 am
OWB
-
MCO
1 stop13h 29m
Multiple Airlines
Sat 9/59:00 pm
MCO
-
OWB
1 stop17h 00m
Multiple Airlines
Deal found 7/24$346
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Sun 9/69:00 am
OWB
-
MCO
1 stop13h 29m
Multiple Airlines
Sun 9/136:40 am
MCO
-
OWB
1 stop13h 40m
Multiple Airlines
Deal found 7/24$348
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/189:00 am
OWB
-
MCO
1 stop12h 11m
Multiple Airlines
Tue 8/259:00 pm
MCO
-
OWB
1 stop17h 00m
Multiple Airlines
Deal found 7/21$349
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/211:55 pm
OWB
-
MCO
1 stop19h 52m
Multiple Airlines
Mon 8/249:00 pm
MCO
-
OWB
1 stop17h 00m
Multiple Airlines
Deal found 7/23$360
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Mon 8/101:55 pm
OWB
-
MCO
1 stop23h 23m
Multiple Airlines
Fri 8/146:00 am
MCO
-
OWB
1 stop14h 20m
Multiple Airlines
Deal found 7/24$370

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 July 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$310
(United Airlines)
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 July 26, 2026.
Use the filters below to find and compare flights from Owensboro to Kissimmee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Sat 11/7

8:45 am-5:40 pm

1 stop7h 55m

Orlando

Sat 11/14

9:00 am-1:40 pm

1 stop5h 40m

$310

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Sat 8/29

9:00 am-10:11 pm

1 stop12h 11m

Orlando

Sun 8/30

6:10 am-7:20 pm

1 stop14h 10m

$343

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Tue 8/18

9:00 am-10:11 pm

1 stop12h 11m

Orlando

Tue 8/25

9:00 pm-1:00 pm

1 stop17h 00m

$349

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Fri 8/21

1:55 pm-10:47 am

1 stop19h 52m

Orlando

Mon 8/24

9:00 pm-1:00 pm

1 stop17h 00m

$360

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Mon 8/10

1:55 pm-2:18 pm

1 stop23h 23m

Orlando

Fri 8/14

6:00 am-7:20 pm

1 stop14h 20m

$370

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Sun 9/6

9:00 am-6:40 am

2 stops20h 40m

Orlando

Sun 9/13

10:48 am-7:20 pm

1 stop9h 32m

$410

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Fri 8/7

1:55 pm-2:18 pm

1 stop23h 23m

Orlando

Tue 8/11

5:24 pm-1:00 pm

2 stops20h 36m

$432

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Sat 8/8

9:00 am-10:15 pm

2 stops12h 15m

Orlando

Wed 8/12

9:38 am-7:20 pm

1 stop10h 42m

$467

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Wed 8/5

1:55 pm-11:35 pm

1 stop8h 40m

Orlando

Sun 8/9

10:18 pm-7:20 pm

2 stops22h 02m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Sorted by cheapest first

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

No data available for this route at this time. Please check back soon.

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.

  • How long is the flight from Owensboro to Kissimmee?

    Departing from Owensboro to Kissimmee will take you 7h 55m. Airlines will cover a distance of 726 mi.

  • 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.

See more FAQs

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