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$431+ Cheap flights from Owensboro (OWB) to Massachusetts

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
OWB — BOS
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Owensboro to Massachusetts

Best flights from Owensboro to Massachusetts
Discover carefully curated flight deals from Owensboro to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 23, 2025.

This Mytrip deal was found by Cheapflights users on 12/22. 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.
Tue 1/61:55 pmOWB - BOS
3 stops33h 02mMultiple Airlines
Sat 1/107:00 amBOS - OWB
3 stops30h 25mMultiple Airlines
Deal found 12/22$431

Find flight deals from Owensboro to Massachusetts

Keep the following information in mind while searching for Owensboro to Massachusetts flight deals. Data was last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$431
(Mytrip)
Provider with most accurate pricing for Owensboro Daviess County-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Owensboro Daviess County-Boston Logan Intl flights.
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From Owensboro Daviess County to Massachusetts
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Owensboro to Massachusetts 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 December 23, 2025.
Use the filters below to find and compare flights from Owensboro to Massachusetts that are best for you.

Fly from

Owensboro

Fly to

Massachusetts

Route

Depart

Return

Price

OwensboroBoston

OWB - BOS

OWBBOS

Owensboro Daviess County

Tue 1/6

1:55 pm-11:57 pm

3 stops33h 02m

Boston Logan Intl

Sat 1/10

7:00 am-12:25 pm

3 stops30h 25m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Best time to book a flight from Owensboro to Massachusetts

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

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

Currently, January is the cheapest month in which you can book a flight from Owensboro to Massachusetts (average of $195). Flying from Owensboro to Massachusetts in June is currently the most expensive (average of $275). 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 Massachusetts. 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 Massachusetts?

    If you book a flight to Massachusetts from Owensboro, you will be flying from Daviess County, which is the city’s only airport. Owensboro Daviess County (OWB) is located 3.6 mi from the center of Owensboro.

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

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

  • How can I find direct flights from Owensboro to Massachusetts?

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

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

    Yes. Cheapflights offers flight deals from Owensboro to Massachusetts 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 Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Owensboro to Massachusetts (average of $195). Flying from Owensboro to Massachusetts in June is currently the most expensive (average of $275). 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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