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Kissimmee

$192+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
OWB — MCO
May 1 — May 81
Fri 5/1
Fri 5/8
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 April 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/132:15 pm
OWB
-
MCO
1 stop6h 22m
Multiple Airlines
Fri 4/172:30 pm
MCO
-
OWB
1 stop5h 20m
Multiple Airlines
Deal found 3/30$192
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/172:15 pm
OWB
-
MCO
1 stop6h 48m
Multiple Airlines
Wed 4/222:35 pm
MCO
-
OWB
1 stop5h 15m
Multiple Airlines
Deal found 3/28$196
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Mon 4/272:15 pm
OWB
-
MCO
1 stop28h 10m
Multiple Airlines
Thu 4/3011:44 am
MCO
-
OWB
1 stop8h 06m
Multiple Airlines
Deal found 3/28$200
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:15 pm
OWB
-
MCO
1 stop8h 05m
Multiple Airlines
Sun 4/196:24 am
MCO
-
OWB
1 stop13h 26m
Multiple Airlines
Deal found 3/31$201
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Sun 4/262:15 pm
OWB
-
MCO
1 stop20h 59m
Multiple Airlines
Thu 4/3011:44 am
MCO
-
OWB
1 stop8h 06m
Multiple Airlines
Deal found 3/28$204
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/222:15 pm
OWB
-
MCO
1 stop6h 48m
Multiple Airlines
Sun 4/265:10 am
MCO
-
OWB
1 stop14h 40m
Multiple Airlines
Deal found 3/31$207

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 April 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$192
(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 April 1, 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

Mon 4/13

2:15 pm-9:37 pm

1 stop6h 22m

Orlando

Fri 4/17

2:30 pm-6:50 pm

1 stop5h 20m

$192

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Mon 4/27

2:15 pm-7:25 pm

1 stop28h 10m

Orlando

Thu 4/30

11:44 am-6:50 pm

1 stop8h 06m

$200

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Wed 4/15

2:15 pm-11:20 pm

1 stop8h 05m

Orlando

Sun 4/19

6:24 am-6:50 pm

1 stop13h 26m

$201

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Sun 4/26

2:15 pm-12:14 pm

1 stop20h 59m

Orlando

Thu 4/30

11:44 am-6:50 pm

1 stop8h 06m

$204

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Wed 4/22

2:15 pm-10:03 pm

1 stop6h 48m

Orlando

Sun 4/26

5:10 am-6:50 pm

1 stop14h 40m

$207

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Fri 4/17

2:15 pm-11:20 pm

1 stop8h 05m

Orlando

Wed 4/22

7:39 pm-12:55 pm

2 stops42h 16m

$234

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Sat 4/11

2:35 pm-5:43 am

2 stops14h 08m

Orlando

Wed 4/15

8:30 am-6:50 pm

1 stop11h 20m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

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

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

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