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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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Aug 12 — Aug 191
Wed 8/12
Wed 8/19
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 13, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:10 am
TYS
-
BOS
1 stop27h 58m
Allegiant Air
Thu 9/312:35 pm
BOS
-
TYS
Nonstop2h 26m
Allegiant Air
Deal found 7/8$199
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 9/269:30 am
TYS
-
BOS
Nonstop2h 15m
Allegiant Air
Sat 10/310:19 am
BOS
-
TYS
1 stop21h 46m
Allegiant Air
Deal found 7/12$206
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/279:30 am
TYS
-
BOS
Nonstop2h 19m
Multiple Airlines
Fri 8/2810:04 am
BOS
-
TYS
1 stop9h 01m
Multiple Airlines
Deal found 7/9$209
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/279:30 am
TYS
-
BOS
Nonstop2h 19m
Multiple Airlines
Mon 8/3110:04 am
BOS
-
TYS
1 stop8h 59m
Multiple Airlines
Deal found 7/9$210
This Super.com deal was found by Cheapflights users on 7/9. 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 8/67:45 pm
BNA
-
BOS
Nonstop2h 35m
JetBlue
Sat 8/86:29 am
BOS
-
BNA
Nonstop2h 51m
JetBlue
Deal found 7/9$211
This Southwest deal was found by Cheapflights users on 7/9. 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 9/1510:20 am
BNA
-
BOS
2 stops7h 15m
Southwest
Sat 9/195:00 am
BOS
-
BNA
Nonstop2h 35m
Southwest
Deal found 7/9$212
This Southwest deal was found by Cheapflights users on 7/10. 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 8/66:50 pm
BNA
-
BOS
Nonstop2h 30m
Southwest
Mon 8/108:55 pm
BOS
-
BNA
1 stop11h 30m
Southwest
Deal found 7/10$213
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 8/86:45 am
TYS
-
BOS
Nonstop2h 20m
Multiple Airlines
Sat 8/1510:04 am
BOS
-
TYS
1 stop11h 59m
Multiple Airlines
Deal found 7/7$216
This Super.com deal was found by Cheapflights users on 7/9. 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 8/281:12 pm
BNA
-
BOS
Nonstop2h 40m
JetBlue
Mon 8/3112:44 pm
BOS
-
BNA
1 stop5h 23m
JetBlue
Deal found 7/9$216
This American Airlines deal was found by Cheapflights users on 7/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:45 am
BNA
-
BOS
1 stop6h 29m
American Airlines
Thu 8/139:16 am
BOS
-
BNA
1 stop6h 24m
American Airlines
Deal found 7/8$217
This Kiwi.com deal was found by Cheapflights users on 7/10. 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.
Tue 10/208:30 am
TYS
-
BOS
Nonstop2h 12m
Multiple Airlines
Sat 10/2410:19 am
BOS
-
TYS
2 stops23h 25m
Multiple Airlines
Deal found 7/10$218
This American Airlines deal was found by Cheapflights users on 7/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:40 am
BNA
-
BOS
1 stop4h 58m
American Airlines
Mon 8/317:43 pm
BOS
-
BNA
1 stop4h 37m
American Airlines
Deal found 7/10$218

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 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$198
(Kiwi.com)

One-way from

$55
(Cheapflightsfares)

Popular in

April

Cheapest in

September

Average price

$425

Good round-trip deal

$510 or less

Good one-way deal

$398 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. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 13, 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

KnoxvilleBoston

TYS - BOS

TYSBOS

Knoxville McGhee Tyson

Thu 8/13

6:12 pm-11:41 pm

1 stop5h 29m

Boston Logan Intl

Mon 8/17

9:00 am-4:33 pm

1 stop7h 33m

$219

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 11/12

12:05 pm-7:55 pm

2 stops6h 50m

Boston Logan Intl

Mon 11/16

1:15 pm-7:50 pm

2 stops7h 35m

$227

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 8/25

10:05 am-6:35 pm

2 stops7h 30m

Boston Logan Intl

Mon 8/31

9:40 am-3:05 pm

2 stops6h 25m

$227
Quickest round-trip

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 8/21

6:50 pm-10:20 pm

Nonstop2h 30m

Boston Logan Intl

Tue 8/25

8:30 am-10:10 am

Nonstop2h 40m

$249

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 8/5

8:50 am-4:00 pm

1 stop6h 10m

Boston Logan Intl

Wed 8/12

10:50 am-5:55 pm

2 stops8h 05m

$252

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 9/9

6:50 am-4:55 pm

2 stops9h 05m

Boston Logan Intl

Sun 9/13

5:55 am-9:55 am

1 stop5h 00m

$257

KnoxvilleBoston

TYS - BOS

TYSBOS

Knoxville McGhee Tyson

Fri 10/30

6:21 pm-11:48 pm

1 stop5h 27m

Boston Logan Intl

Tue 11/3

8:00 am-1:49 pm

1 stop5h 49m

$263

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 10/16

8:20 pm-11:50 pm

Nonstop2h 30m

Boston Logan Intl

Tue 10/20

2:50 pm-7:40 pm

2 stops5h 50m

$267

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 9/15

10:05 am-6:35 pm

2 stops7h 30m

Boston Logan Intl

Sun 9/20

5:55 am-9:55 am

1 stop5h 00m

$277

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 8/7

1:35 pm-9:53 pm

2 stops7h 18m

Boston Logan Intl

Mon 8/10

5:44 pm-11:16 pm

1 stop6h 32m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

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, October is the cheapest month in which you can book a flight from Kentucky to Boston (average of $125). Flying from Kentucky to Boston in June is currently the most expensive (average of $274). 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 13, 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.

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 July 13, 2026.

The most flights from USKY to BOS are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

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

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 5h 29m. Fly via Delta, Southwest, or United Airlines to get the fastest option. Airlines will cover a distance of 829 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: KLM (83%), Scandinavian Airlines (81%), Air France( 80%).

  • What are the cheapest flights from Kentucky to Boston?

    While on average a flight from Kentucky to Boston is generally $861, our data shows the cheapest flight currently is $306. When looking at the most popular route, (Cincinnati Cinci./N. Kentucky - Boston Logan Intl), you can expect to pay $277 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, October is the cheapest month in which you can book a flight from Kentucky to Boston (average of $125). Flying from Kentucky to Boston in June is currently the most expensive (average of $274). 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
Brockton
Hampton Beach
Seekonk
Cranston
Warwick
Dedham
Peabody
Randolph
Auburn
Fitchburg
York Beach
Chelsea
Londonderry
Swansea
North Falmouth
Smithfield
Braintree

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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 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$139Average$384FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$236Average$406FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$248Average$371FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$294Average$437FlexibilityNo cancel feeOn-time69%

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