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$55+ Cheap flights from Kentucky to Boston (BOS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheap flight deals from Kentucky to Boston

Keep the following information in mind while searching for Kentucky to Boston flight deals. Data was last updated November 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$104
(Cheapflightsfares)

One-way from

$55
(Priceline)

Popular in

April

Cheapest in

September

Average price

$359

Good round-trip deal

$483 or less

Good one-way deal

$258 or less
Provider with most accurate pricing for Louisville Intl-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-Boston Logan Intl flights.
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From Kentucky to Boston Logan Intl
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One-way flight from Kentucky to Boston Logan Intl
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Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Kentucky to Boston Logan Intl.
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Price to beat on a one-way flight from Kentucky to Boston Logan Intl.
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Find flight deals from Kentucky to Boston

Cheapest flights from Kentucky to Boston
Explore the most affordable flight options available from Kentucky to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2025.

This Kissandfly.com deal was found by Cheapflights users on 11/4. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:46 amBNA - BOS
Nonstop2h 29mJetBlue
Sun 12/77:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 11/4$115
This Trip.com deal was found by Cheapflights users on 11/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/69:46 amBNA - BOS
Nonstop2h 29mJetBlue
Mon 12/83:45 pmBOS - BNA
Nonstop3h 04mJetBlue
Deal found 11/4$121
This JetBlue deal was found by Cheapflights users on 11/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:00 amBNA - BOS
Nonstop2h 28mJetBlue
Thu 12/47:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 11/4$127
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:55 pmBNA - BOS
1 stop5h 20mSouthwest
Sun 12/76:50 pmBOS - BNA
Nonstop3h 00mSouthwest
Deal found 11/3$137
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:45 pmBNA - BOS
Nonstop2h 30mSouthwest
Sat 1/38:05 pmBOS - BNA
Nonstop2h 55mSouthwest
Deal found 11/3$141
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/29:55 amBNA - BOS
Nonstop2h 35mSouthwest
Thu 12/45:45 amBOS - BNA
2 stops6h 10mSouthwest
Deal found 11/3$142
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/134:55 pmBNA - BOS
1 stop4h 00mSouthwest
Mon 12/155:35 pmBOS - BNA
1 stop4h 30mSouthwest
Deal found 11/4$147
This JetBlue deal was found by Cheapflights users on 11/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:00 amBNA - BOS
Nonstop2h 28mJetBlue
Tue 12/27:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 11/2$150
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/199:55 amBNA - BOS
Nonstop2h 35mSouthwest
Sat 11/225:05 amBOS - BNA
Nonstop2h 55mSouthwest
Deal found 11/3$151
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:30 amTYS - BOS
Nonstop2h 13mAllegiant Air
Tue 11/1110:33 amBOS - TYS
Nonstop2h 28mAllegiant Air
Deal found 11/3$154
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:30 amTYS - BOS
Nonstop2h 13mAllegiant Air
Sun 11/1611:33 amBOS - TYS
Nonstop2h 32mAllegiant Air
Deal found 11/2$158
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/48:30 amTYS - BOS
1 stop25h 27mMultiple Airlines
Sun 12/79:00 amBOS - TYS
Nonstop2h 31mMultiple Airlines
Deal found 11/2$162

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky 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 November 4, 2025.
Use the filters below to find and compare flights from Kentucky to Boston that are best for you.

Fly from

Kentucky

Fly to

Boston

Route

Depart

Return

Price

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 12/5

7:05 am-10:53 am

Nonstop2h 48m

Boston Logan Intl

Sun 12/7

7:50 am-9:57 am

Nonstop3h 07m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 12/12

7:45 pm-11:15 pm

Nonstop2h 30m

Boston Logan Intl

Mon 12/15

6:00 pm-7:55 pm

Nonstop2h 55m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 12/2

7:00 am-10:28 am

Nonstop2h 28m

Boston Logan Intl

Thu 12/4

7:00 am-9:01 am

Nonstop3h 01m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 12/11

6:40 pm-10:15 pm

Nonstop2h 35m

Boston Logan Intl

Sun 12/14

5:15 am-9:45 am

1 stop5h 30m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 12/4

9:30 am-5:20 pm

1 stop6h 50m

Boston Logan Intl

Thu 12/11

6:00 pm-7:55 pm

Nonstop2h 55m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 12/4

3:00 pm-9:40 pm

1 stop5h 40m

Boston Logan Intl

Sun 12/7

5:00 am-6:55 am

Nonstop2h 55m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Sun 12/14

7:45 pm-11:15 pm

Nonstop2h 30m

Boston Logan Intl

Sat 1/3

8:05 pm-10:00 pm

Nonstop2h 55m

$141

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 1/20

9:50 am-1:20 pm

Nonstop2h 30m

Boston Logan Intl

Sun 1/25

5:10 am-10:10 am

1 stop6h 00m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 11/26

6:00 am-9:28 am

Nonstop2h 28m

Boston Logan Intl

Wed 12/3

3:45 pm-5:49 pm

Nonstop3h 04m

$150

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 11/26

6:00 am-9:28 am

Nonstop2h 28m

Boston Logan Intl

Tue 12/2

7:00 am-9:01 am

Nonstop3h 01m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Boston

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

What is the cheapest month to book a flight from Kentucky to Boston?

Currently, September is the cheapest month in which you can book a flight from Kentucky to Boston (average of $139). Flying from Kentucky to Boston in December is currently the most expensive (average of $248). 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.

What is the cheapest time of day to fly from KY to BOS?

Find hourly flight availability from Kentucky to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2025.

It’s typically best to fly out from Kentucky to Boston in the evening. Doing so could potentially save you 37% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Kentucky to Boston?

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Boston. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kentucky to Boston flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Kentucky to Boston

Explore weekly flight availability from Kentucky to Boston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 4, 2025.

The most flights from USKY to BOS are scheduled on a Monday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Boston. 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 into for flights to Boston from Kentucky?

    Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Kentucky. Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • How popular is this Kentucky to Boston flight route?

    This flight path from Kentucky to Boston Logan Intl was viewed by 10 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Kentucky to Boston?

    There are many flights that can get you from Kentucky to Boston in 2h 28m. Fly via Delta, Southwest, or JetBlue to get the fastest option. Airlines will cover a distance of 941 mi. All flights are typically nonstop.

  • What are the cheapest airlines to fly from Kentucky to Boston one-way?

    For one-way options, check prices for Allegiant Air. According to our data, you can fly for as low as $61. Users have also found prices from $69 and $69 on Delta and Southwest, respectively.

  • What are the most popular routes from Kentucky to Boston?

    The most popular flight routes from Kentucky to Boston are Cincinnati Cinci./N. Kentucky - Boston Logan Intl, Nashville Intl - Boston Logan Intl and Louisville Intl - Boston Logan Intl.

  • What are the most reliable airlines from Kentucky to Boston?

    Before booking your flight to Boston from Kentucky, check out the most reliable airlines to get you to your destination on time: Scandinavian Airlines (100%), Republic Airways (85%), Delta( 80%).

  • What are the cheapest flights from Kentucky to Boston?

    While on average a flight from Kentucky to Boston is generally $477, our data shows the cheapest flight currently is $143. When looking at the most popular route, (Cincinnati Cinci./N. Kentucky - Boston Logan Intl), you can expect to pay $157 for that flight.

  • Can I find deals for flights from Kentucky to Boston that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Kentucky 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.

  • What is the cheapest month to book a flight from Kentucky to Boston?

    Currently, September is the cheapest month in which you can book a flight from Kentucky to Boston (average of $139). Flying from Kentucky to Boston in December is currently the most expensive (average of $248). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Top 5 airlines flying from Kentucky to Boston

Discover the top 5 airlines that operate flights from Kentucky to Boston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$139Average$342FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$171Average$215FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$216Average$385FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$248Average$379FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$271Average$442FlexibilityNo cancel feeOn-time69%

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