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$374+ Cheap flights from Owensboro to Boston (OWB - BOS)

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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
OWB — BOS
Jul 11 — Jul 181
Sat 7/11
Sat 7/18
1 adult, Economy
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Cheap flight deals from Owensboro to Boston

Cheapest flights from Owensboro to Boston
Explore the most affordable flight options available from Owensboro to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 11, 2026.

This KAYAK deal was found by Cheapflights users on 6/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:00 am
OWB
-
BOS
2 stops28h 22m
Multiple Airlines
Tue 8/1812:42 pm
BOS
-
OWB
2 stops25h 13m
Multiple Airlines
Deal found 6/8$374
This KAYAK deal was found by Cheapflights users on 6/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:00 am
OWB
-
BOS
2 stops28h 41m
Multiple Airlines
Sat 8/225:01 am
BOS
-
OWB
2 stops8h 54m
Multiple Airlines
Deal found 6/8$394
This KAYAK deal was found by Cheapflights users on 6/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:00 am
OWB
-
BOS
1 stop13h 51m
Multiple Airlines
Thu 8/274:30 pm
BOS
-
OWB
2 stops21h 25m
Multiple Airlines
Deal found 6/8$413
This KAYAK deal was found by Cheapflights users on 6/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:00 am
OWB
-
BOS
2 stops31h 22m
Multiple Airlines
Wed 7/812:45 pm
BOS
-
OWB
2 stops25h 10m
Multiple Airlines
Deal found 6/6$414
This KAYAK deal was found by Cheapflights users on 6/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:00 am
OWB
-
BOS
1 stop13h 51m
Multiple Airlines
Thu 9/1711:25 am
BOS
-
OWB
1 stop26h 30m
Multiple Airlines
Deal found 6/11$443

Find flight deals from Owensboro to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Owensboro (OWB) to Boston (BOS). 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 June 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$374
(KAYAK)
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.
Search Deals
From Owensboro Daviess County to Boston Logan Intl
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Owensboro to Boston 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 June 11, 2026.
Use the filters below to find and compare flights from Owensboro to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OwensboroBoston

OWB - BOS

OWBBOS

Owensboro Daviess County

Thu 8/20

9:00 am-2:41 pm

2 stops28h 41m

Boston Logan Intl

Sat 8/22

5:01 am-12:55 pm

2 stops8h 54m

$394

OwensboroBoston

OWB - BOS

OWBBOS

Owensboro Daviess County

Wed 8/26

9:00 am-11:51 pm

1 stop13h 51m

Boston Logan Intl

Thu 8/27

4:30 pm-12:55 pm

2 stops21h 25m

$413

OwensboroBoston

OWB - BOS

OWBBOS

Owensboro Daviess County

Wed 7/1

9:00 am-11:51 pm

1 stop13h 51m

Boston Logan Intl

Wed 7/8

12:45 pm-12:55 pm

2 stops25h 10m

$425

OwensboroBoston

OWB - BOS

OWBBOS

Owensboro Daviess County

Tue 9/8

9:00 am-11:51 pm

1 stop13h 51m

Boston Logan Intl

Thu 9/17

11:25 am-12:55 pm

1 stop26h 30m

$443
Quickest round-trip

OwensboroBoston

OWB - BOS

OWBBOS

Owensboro Daviess County

Wed 7/15

9:00 am-2:48 pm

2 stops28h 48m

Boston Logan Intl

Wed 7/29

8:10 am-12:55 pm

1 stop5h 45m

$492

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on Owensboro-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Owensboro-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Owensboro-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Owensboro-Boston flights, Cheapflights users trust FlightHub the most. FlightHub 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-Boston 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 Boston

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

Related info for your journey

Find useful and relevant information for your journey from Owensboro to Boston. 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 Boston that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Owensboro to Boston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Waltham
Cambridge
Concord
Hampton Beach
Brockton
Watertown
Seekonk
Cranston
Warwick
Peabody
Auburn
York Beach
Chelsea
Londonderry
Swansea
Old Orchard Beach
Lowell
Smithfield
Braintree
Sandwich

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