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$441+ Cheap flights from Owensboro to Key West (OWB - EYW)

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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
OWB — EYW
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Owensboro to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Owensboro (OWB) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$441
(Mytrip)
Provider with most accurate pricing for Owensboro Daviess County-Key West flight deals.
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Provider most trusted by Cheapflights users for Owensboro Daviess County-Key West flights.
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From Owensboro Daviess County to Key West
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Find flight deals from Owensboro to Key West

Cheapest flights from Owensboro to Key West
Explore the most affordable flight options available from Owensboro to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This Mytrip deal was found by Cheapflights users on 1/13. 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.
Thu 1/298:40 am
OWB
-
EYW
3 stops27h 50m
Multiple Airlines
Mon 2/22:25 pm
EYW
-
OWB
2 stops21h 45m
Multiple Airlines
Deal found 1/13$441

Cheapflights Fare Finder

 
Customize your flight search to find flights from Owensboro to Key West 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 January 15, 2026.
Use the filters below to find and compare flights from Owensboro to Key West that are best for you.

Fly from

Owensboro

Fly to

Key West

Route

Depart

Return

Price

OwensboroKey West

OWB - EYW

OWBEYW

Owensboro Daviess County

Thu 1/29

8:40 am-1:30 pm

3 stops27h 50m

Key West

Mon 2/2

2:25 pm-11:10 am

2 stops21h 45m

$441

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Compare providers for flights from Owensboro to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Owensboro to Key West in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Owensboro-Key West flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Owensboro-Key West flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Owensboro-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Owensboro-Key West flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Owensboro-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Owensboro to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West 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 Key West

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

Currently, April is the cheapest month in which you can book a flight from Owensboro to Key West (average of $219). Flying from Owensboro to Key West in December is currently the most expensive (average of $310). 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 Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Owensboro to Key West that include hotel bookings?

    Yes. In addition to deals on Owensboro to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Owensboro to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Owensboro to Key West.

  • Can I find deals for business class flights from Owensboro to Key West?

    Yes. Cheapflights offers flight deals from Owensboro to Key West 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 Key West?

    Currently, April is the cheapest month in which you can book a flight from Owensboro to Key West (average of $219). Flying from Owensboro to Key West in December is currently the most expensive (average of $310). 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.

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