$325+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
OWB — MCO
Oct 7 — Oct 141
Round-trip
1 adult, Economy
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Find cheap flights from Owensboro 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 Owensboro to Kissimmee
Cheapest
Best
Last-minute
Cheapest flights from Owensboro to KissimmeeExplore 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 September 7, 2026.
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 September 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/99:00 am -
1 stop14h 08m
Sun 10/115:20 am -
1 stop8h 40m
Deal found 9/5![Multiple Airlines logo]()
$325
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Tue 12/82:25 pm -
1 stop8h 29m
Sat 12/129:28 am -
1 stop5h 17m
Deal found 9/6![United Airlines logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Thu 9/179:00 am -
2 stops13h 59m
Mon 9/216:40 am -
1 stop13h 40m
Deal found 9/2![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 9/199:00 am -
1 stop9h 46m
Wed 9/236:40 am -
1 stop13h 40m
Deal found 9/5![Multiple Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/131:55 pm -
1 stop20h 38m
Thu 9/176:40 am -
1 stop13h 40m
Deal found 9/2![Multiple Airlines logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 9/199:00 am -
2 stops15h 45m
Tue 9/228:51 pm -
1 stop17h 09m
Deal found 9/5![Multiple Airlines logo]()
$488
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Mon 11/168:45 am -
1 stop5h 31m
Wed 11/184:32 pm -
1 stop7h 33m
Deal found 9/2![United Airlines logo]()
$618
Best flights from Owensboro to KissimmeeDiscover carefully curated flight deals from Owensboro to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
Discover carefully curated flight deals from Owensboro to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/51:55 pm -
1 stop20h 38m
Fri 10/96:55 am -
2 stops13h 25m
Deal found 9/7![Multiple Airlines logo]()
$405
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Tue 12/89:00 am -
2 stops9h 27m
Sat 12/129:00 am -
1 stop5h 45m
Deal found 9/6![United Airlines logo]()
$420
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Thu 9/179:00 am -
2 stops13h 59m
Mon 9/216:40 am -
1 stop13h 40m
Deal found 9/2![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/69:00 am -
2 stops37h 04m
Mon 10/125:20 am -
1 stop8h 40m
Deal found 9/7![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 9/199:00 am -
1 stop9h 46m
Tue 9/228:51 pm -
1 stop17h 09m
Deal found 9/5![Multiple Airlines logo]()
$502
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Mon 11/168:45 am -
1 stop5h 31m
Wed 11/184:32 pm -
1 stop7h 33m
Deal found 9/3![United Airlines logo]()
$618
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Fri 2/122:25 pm -
1 stop25h 14m
Tue 2/239:00 am -
1 stop5h 40m
Deal found 9/2![United Airlines logo]()
$624
Last-minute flights from Owensboro to KissimmeeDiscover last-minute flight deals from Owensboro to Kissimmee. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Owensboro to Kissimmee. Data last updated September 7, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/131:55 pm -
1 stop20h 38m
Thu 9/176:40 am -
1 stop13h 40m
Deal found 9/2![Multiple Airlines logo]()
$439
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 September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $320 (United Airlines) |
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 7,457,451 searches. Data last updated September 7, 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
Cheapest round-trip
OwensboroOrlando
OWB Owensboro Daviess County - MCO Orlando
OWBMCO
Owensboro Daviess County
Mon 10/5
1:55 pm-11:33 am
1 stop20h 38m
Orlando
Fri 10/9
6:55 am-7:20 pm
2 stops13h 25m
$405
OwensboroOrlando
OWB Owensboro Daviess County - MCO Orlando
OWBMCO
Owensboro Daviess County
Thu 9/17
9:00 am-11:59 pm
2 stops13h 59m
Orlando
Mon 9/21
6:40 am-7:20 pm
1 stop13h 40m
$412
OwensboroOrlando
OWB Owensboro Daviess County - MCO Orlando
OWBMCO
Owensboro Daviess County
Tue 12/8
9:00 am-7:27 pm
2 stops9h 27m
Orlando
Sat 12/12
9:00 am-1:45 pm
1 stop5h 45m
$420
OwensboroOrlando
OWB Owensboro Daviess County - MCO Orlando
OWBMCO
Owensboro Daviess County
Tue 10/6
9:00 am-11:04 pm
2 stops37h 04m
Orlando
Mon 10/12
5:20 am-1:00 pm
1 stop8h 40m
$470
OwensboroOrlando
OWB Owensboro Daviess County - MCO Orlando
OWBMCO
Owensboro Daviess County
Sat 9/19
9:00 am-7:46 pm
1 stop9h 46m
Orlando
Tue 9/22
8:51 pm-1:00 pm
1 stop17h 09m
$502
Quickest round-trip
OwensboroOrlando
OWB Owensboro Daviess County - MCO Orlando
OWBMCO
Owensboro Daviess County
Mon 11/16
8:45 am-3:16 pm
1 stop5h 31m
Orlando
Wed 11/18
4:32 pm-11:05 pm
1 stop7h 33m
$618
OwensboroOrlando
OWB Owensboro Daviess County - MCO Orlando
OWBMCO
Owensboro Daviess County
Fri 2/12
2:25 pm-4:39 pm
1 stop25h 14m
Orlando
Tue 2/23
9:00 am-1:40 pm
1 stop5h 40m
$624
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.
OWB-MCO
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
OWB-K1S
OWB-MCO
No data available for this route at this time. Please check back soon.
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