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Kissimmee

$296+ Cheap flights from Owensboro (OWB) 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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
OWB — MCO
Jun 25 — Jul 21
Thu 6/25
Thu 7/2
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 May 26, 2026.

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.
Tue 7/214:25 pm
OWB
-
MCO
2 stops36h 06m
Multiple Airlines
Mon 7/279:38 am
MCO
-
OWB
1 stop10h 12m
Multiple Airlines
Deal found 5/24$483
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.
Sat 6/69:00 am
OWB
-
MCO
2 stops11h 47m
Multiple Airlines
Sun 6/72:50 pm
MCO
-
OWB
1 stop5h 00m
Multiple Airlines
Deal found 5/24$742
This Kiwi.com deal was found by Cheapflights users on 5/23. 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.
Sun 5/242:15 pm
OWB
-
MCO
1 stop6h 38m
Multiple Airlines
Tue 5/2611:20 pm
MCO
-
OWB
2 stops20h 30m
Multiple Airlines
Deal found 5/23$888

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 May 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$409
(Kiwi.com)

One-way from

$296
(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
One-way flight 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 May 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

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Tue 7/7

4:25 pm-9:25 pm

1 stop28h 00m

Orlando

Mon 7/13

7:21 pm-12:55 pm

2 stops18h 34m

$409

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Tue 7/21

4:25 pm-5:31 am

2 stops36h 06m

Orlando

Mon 7/27

9:38 am-6:50 pm

1 stop10h 12m

$483

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Thu 6/11

2:15 pm-9:55 pm

1 stop6h 40m

Orlando

Sun 6/14

11:15 pm-6:50 pm

2 stops20h 35m

$576
Quickest round-trip

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Sat 6/6

9:00 am-9:47 pm

2 stops11h 47m

Orlando

Sun 6/7

2:50 pm-6:50 pm

1 stop5h 00m

$742
Cheapest one-way
Quickest one-way

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Sun 7/5

2:15 pm-12:54 am

1 stop9h 39m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

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.

  • 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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