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$50+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
1 adult, Economy
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Cheap 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 July 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sat 9/59:30 am
TYS
-
BOS
Nonstop2h 15m
Allegiant Air
Thu 9/1010:15 am
BOS
-
TYS
Nonstop2h 26m
Allegiant Air
Deal found 7/29$180
This Cheapflightsfares deal was found by Cheapflights users on 7/25. 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 8/229:30 am
TYS
-
BOS
Nonstop2h 19m
Allegiant Air
Sat 8/2912:39 pm
BOS
-
TYS
Nonstop2h 28m
Allegiant Air
Deal found 7/25$185
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sun 9/69:30 am
TYS
-
BOS
Nonstop2h 15m
Allegiant Air
Sat 9/1212:35 pm
BOS
-
TYS
Nonstop2h 26m
Allegiant Air
Deal found 7/29$188
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 9/39:30 am
TYS
-
BOS
Nonstop2h 15m
Allegiant Air
Thu 9/1010:15 am
BOS
-
TYS
Nonstop2h 26m
Allegiant Air
Deal found 7/26$197
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Thu 9/39:30 am
TYS
-
BOS
Nonstop2h 15m
Allegiant Air
Sat 9/1212:35 pm
BOS
-
TYS
Nonstop2h 26m
Allegiant Air
Deal found 7/29$198
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:45 am
TYS
-
BOS
Nonstop2h 20m
Allegiant Air
Sat 8/2212:39 pm
BOS
-
TYS
Nonstop2h 28m
Allegiant Air
Deal found 7/28$199
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:30 am
TYS
-
BOS
Nonstop2h 15m
Allegiant Air
Sat 10/39:02 am
BOS
-
TYS
Nonstop2h 30m
Allegiant Air
Deal found 7/29$205
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Fri 10/99:35 pm
TYS
-
BOS
1 stop11h 54m
Allegiant Air
Sat 10/249:02 am
BOS
-
TYS
Nonstop2h 30m
Allegiant Air
Deal found 7/28$206
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:07 am
BNA
-
BOS
1 stop5h 00m
JetBlue
Mon 8/245:16 am
BOS
-
BNA
1 stop5h 46m
JetBlue
Deal found 7/28$211
This Super.com deal was found by Cheapflights users on 7/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:04 am
BNA
-
BOS
1 stop7h 30m
JetBlue
Tue 9/86:05 am
BOS
-
BNA
1 stop4h 55m
JetBlue
Deal found 7/26$212
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:03 pm
BNA
-
BOS
1 stop4h 56m
JetBlue
Sun 8/305:01 am
BOS
-
BNA
1 stop5h 59m
JetBlue
Deal found 7/28$213
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:30 am
BNA
-
BOS
1 stop5h 51m
JetBlue
Wed 9/235:15 am
BOS
-
BNA
1 stop5h 17m
JetBlue
Deal found 7/28$214

Find flight deals from Kentucky to Boston

Keep the following information in mind while searching for Kentucky to Boston flight deals. Data was last updated July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$185
(Cheapflightsfares)

One-way from

$50
(Cheapflightsfares)

Popular in

April

Cheapest in

October

Average price

$454

Good round-trip deal

$455 or less

Good one-way deal

$306 or less
Provider with most accurate pricing for Louisville Intl-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Boston Logan Intl flights.
Search Deals
From Kentucky to Boston Logan Intl
Search Deals
One-way flight from Kentucky to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Kentucky to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Kentucky to Boston Logan Intl.
Search Deals

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 July 29, 2026.
Use the filters below to find and compare flights from Kentucky to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 12/31

6:44 pm-11:57 pm

1 stop4h 13m

Boston Logan Intl

Wed 1/6

7:10 am-12:06 pm

1 stop5h 56m

$265

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Sat 10/3

10:30 am-6:00 pm

1 stop6h 30m

Boston Logan Intl

Mon 10/5

6:45 pm-8:38 pm

Nonstop2h 53m

$281

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 12/8

6:00 am-12:47 pm

1 stop5h 47m

Boston Logan Intl

Thu 12/10

6:00 am-10:14 am

1 stop5h 14m

$285

KnoxvilleBoston

TYS - BOS

TYSBOS

Knoxville McGhee Tyson

Sat 9/26

5:45 pm-1:17 am

1 stop7h 32m

Boston Logan Intl

Sat 10/3

5:30 am-12:58 pm

1 stop7h 28m

$299
Quickest round-trip

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 8/18

1:35 pm-5:05 pm

Nonstop2h 30m

Boston Logan Intl

Thu 8/20

5:25 am-7:00 am

Nonstop2h 35m

$307

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 8/25

10:05 am-6:35 pm

2 stops7h 30m

Boston Logan Intl

Tue 9/1

2:45 pm-7:55 pm

2 stops6h 10m

$317

KnoxvilleBoston

TYS - BOS

TYSBOS

Knoxville McGhee Tyson

Wed 8/19

5:30 pm-10:10 pm

1 stop4h 40m

Boston Logan Intl

Fri 8/21

9:40 am-6:35 pm

2 stops8h 55m

$318

BlountvilleBoston

TRI - BOS

TRIBOS

Blountville Tri Cities TN/VA

Wed 9/9

4:57 pm-10:24 pm

1 stop5h 27m

Boston Logan Intl

Sun 9/13

6:00 am-10:38 am

1 stop4h 38m

$319

KnoxvilleBoston

TYS - BOS

TYSBOS

Knoxville McGhee Tyson

Fri 9/11

5:45 pm-10:33 pm

1 stop4h 48m

Boston Logan Intl

Sun 9/13

5:40 am-10:18 am

1 stop4h 38m

$319

BlountvilleBoston

TRI - BOS

TRIBOS

Blountville Tri Cities TN/VA

Wed 9/16

4:57 pm-10:24 pm

1 stop5h 27m

Boston Logan Intl

Mon 9/21

5:56 pm-11:01 pm

1 stop5h 05m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 60 resultsSorted by cheapest first
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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, January is the cheapest month in which you can book a flight from Kentucky to Boston (average of $357). Flying from Kentucky to Boston in April is currently the most expensive (average of $503). 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 July 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kentucky to Boston as you normally would.

How much does it cost to fly round-trip from Kentucky to Boston?

Airfare is below average for this route at the moment.
Kentucky to Boston flights typically cost between $364 and $469 in December.
The cheapest round-trip price found within the last 5 days was $276 on Allegiant Air (Dec 10-Dec 13).

How far ahead should I book a flight from Kentucky to Boston?

Booking 73 days in advance of your planned departure date is, on average, the best time to get cheap flights from Kentucky to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 8 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 4h 13m. Fly via United Airlines, JetBlue, or Delta to get the fastest option. Airlines will cover a distance of 941 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $99. Users have also found prices from $124 and $125 on Delta and American Airlines, 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 (84%), KLM (83%), Delta( 82%).

  • What are the cheapest flights from Kentucky to Boston?

    While on average a flight from Kentucky to Boston is generally $539, our data shows the cheapest flight currently is $277. When looking at the most popular route, (Cincinnati Cinci./N. Kentucky - Boston Logan Intl), you can expect to pay $237 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, January is the cheapest month in which you can book a flight from Kentucky to Boston (average of $357). Flying from Kentucky to Boston in April is currently the most expensive (average of $503). 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
Waltham
Cambridge
Concord
Randolph
Brockton
Seekonk
Hampton Beach
Cranston
Warwick
Peabody
Dedham
Auburn
York Beach
Chelsea
Londonderry
Swansea
Fitchburg
North Falmouth
Braintree
Revere

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Top 4 airlines flying from Kentucky to Boston

Discover the top 4 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 July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$139Average$391FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$384FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$293Average$413FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$294Average$437FlexibilityNo cancel feeOn-time69%

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