HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kissimmee

$268+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
OWB — MCO
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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.

Find 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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Tue 11/113:10 pmOWB - MCO
1 stop18h 20mMultiple Airlines
Fri 11/149:00 pmMCO - OWB
1 stop16h 25mMultiple Airlines
Deal found 10/28$268
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Fri 12/58:40 amOWB - MCO
1 stop8h 51mMultiple Airlines
Sun 12/711:15 amMCO - OWB
1 stop26h 10mMultiple Airlines
Deal found 10/30$296
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/133:10 pmOWB - MCO
1 stop18h 20mMultiple Airlines
Mon 11/177:42 pmMCO - OWB
2 stops17h 43mMultiple Airlines
Deal found 10/28$300
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Wed 11/123:10 pmOWB - MCO
1 stop16h 57mMultiple Airlines
Sun 11/166:00 amMCO - OWB
2 stops31h 25mMultiple Airlines
Deal found 10/30$347
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/283:10 pmOWB - MCO
1 stop6h 09mMultiple Airlines
Fri 12/512:17 pmMCO - OWB
1 stop25h 08mMultiple Airlines
Deal found 10/29$357

Cheap flight deals from Owensboro to Kissimmee

Keep the following information in mind while searching for Owensboro to Kissimmee flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$268
(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 October 30, 2025.
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

Tue 11/11

3:10 pm-10:30 am

1 stop18h 20m

Orlando

Fri 11/14

9:00 pm-12:25 pm

1 stop16h 25m

$268

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Fri 12/5

8:40 am-6:31 pm

1 stop8h 51m

Orlando

Sun 12/7

11:15 am-12:25 pm

1 stop26h 10m

$296

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Thu 11/13

3:10 pm-10:30 am

1 stop18h 20m

Orlando

Mon 11/17

7:42 pm-12:25 pm

2 stops17h 43m

$300

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Wed 11/12

3:10 pm-9:07 am

1 stop16h 57m

Orlando

Sun 11/16

6:00 am-12:25 pm

2 stops31h 25m

$347

OwensboroOrlando

OWB - MCO

OWBMCO

Owensboro Daviess County

Fri 11/28

3:10 pm-10:19 pm

1 stop6h 09m

Orlando

Fri 12/5

12:17 pm-12:25 pm

1 stop25h 08m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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 December is currently the most expensive (average of $107). 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 December is currently the most expensive (average of $107). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Owensboro to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
Cincinnati to Orlando flights
Cincinnati to Fort Lauderdale flights
Cincinnati to Miami flights
Cincinnati to Tampa flights
Cincinnati to Fort Myers flights
Nashville to Orlando flights
Nashville to Fort Lauderdale flights
Louisville to Orlando flights
Nashville to Miami flights
Cincinnati to Orlando Sanford Intl flights
Louisville to Miami flights
Cincinnati to St Petersburg flights
Knoxville to Orlando Sanford Intl flights
Nashville to Tampa flights
Lexington to Orlando flights
Louisville to Fort Lauderdale flights
Louisville to Fort Myers flights
Louisville to Tampa flights
Cincinnati to Key West flights
Lexington to Orlando Sanford Intl flights
Knoxville to Miami flights
Knoxville to Orlando flights
Cincinnati to Sarasota flights
Lexington to Miami flights
Nashville to Fort Myers flights
Lexington to Sarasota flights
Nashville to West Palm Beach flights
Nashville to Sarasota flights
Nashville to Jacksonville flights
Knoxville to Fort Lauderdale flights
Lexington to Tampa flights
Nashville to Key West flights
Knoxville to St Petersburg flights
Knoxville to Sarasota flights
Nashville to Pensacola flights
Cincinnati to Valparaiso flights
Cincinnati to Pensacola flights
Lexington to Fort Lauderdale flights
Knoxville to Key West flights
Louisville to West Palm Beach flights
Louisville to Orlando Sanford Intl flights
Huntington to Fort Lauderdale flights
Knoxville to Tampa flights
Cincinnati to Panama City flights
Louisville to Sarasota flights
Cincinnati to Jacksonville flights
Evansville to Orlando flights
Lexington to Fort Myers flights
Louisville to Key West flights
Cincinnati to West Palm Beach flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.