$47 Find Cheap Flights from Boston to Kentucky - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Kentucky departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Boston to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisville1 stop$277
Lexington
Lexington1 stop$319
Paducah
Paducah1 stop$403
Owensboro
Owensboro2 stops$465
Nashville
Nashville1 stop$211
Louisville
Louisville1 stop$277
Lexington
Lexington1 stop$319
Paducah
Paducah1 stop$403
Owensboro
Owensboro2 stops$465
Nashville
Nashville1 stop$211

Book Cheap Boston to Kentucky Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Kentucky that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Kentucky

Sat, Aug 22 - Sat, Aug 29
Allegiant Air Logo
12:39 pm - 3:07 pm
BOS
-
TYS
2h 28mnonstop
Allegiant Air Logo
9:30 am - 11:49 am
TYS
-
BOS
2h 19mnonstop
$115Allegiant Air
Sun, Nov 8 - Sat, Nov 14
Allegiant Air Logo
9:09 am - 11:39 am
BOS
-
TYS
2h 30mnonstop
Allegiant Air Logo
6:00 am - 8:19 am
TYS
-
BOS
2h 19mnonstop
$119Allegiant Air
Sat, Sep 5 - Thu, Sep 10
Multiple Airlines Logo
12:35 pm - 3:01 pm
BOS
-
TYS
2h 26mnonstop
Multiple Airlines Logo
1:31 pm - 10:51 am
TYS
-
BOS
21h 20m
1 stop
$202Multiple Airlines
Sat, Sep 5 - Sun, Sep 6
Multiple Airlines Logo
10:04 am - 7:53 pm
BOS
-
TYS
9h 49m
1 stop
Multiple Airlines Logo
9:30 am - 11:45 am
TYS
-
BOS
2h 15mnonstop
$204Multiple Airlines
Tue, Aug 18 - Tue, Aug 18
JetBlue Logo
5:01 am - 10:02 am
BOS
-
BNA
6h 01m
1 stop
JetBlue Logo
5:58 pm - 11:59 pm
BNA
-
BOS
5h 01m
1 stop
$211JetBlue
Sat, Aug 22 - Mon, Aug 24
JetBlue Logo
5:01 am - 10:02 am
BOS
-
BNA
6h 01m
1 stop
JetBlue Logo
6:03 pm - 11:59 pm
BNA
-
BOS
4h 56m
1 stop
$211JetBlue
Tue, Aug 18 - Wed, Aug 26
Delta Logo
7:45 pm - 9:49 pm
BOS
-
BNA
3h 04mnonstop
Delta Logo
5:35 pm - 9:19 pm
BNA
-
BOS
2h 44mnonstop
$227Delta
Wed, Aug 19 - Tue, Aug 25
Delta Logo
7:45 pm - 9:49 pm
BOS
-
BNA
3h 04mnonstop
Delta Logo
5:35 pm - 9:19 pm
BNA
-
BOS
2h 44mnonstop
$227Delta
Thu, Oct 15 - Sat, Oct 17
Frontier Logo
9:15 am - 5:38 pm
BOS
-
BNA
9h 23m
1 stop
Frontier Logo
6:34 pm - 8:20 am
BNA
-
BOS
12h 46m
1 stop
$246Frontier
Sat, Oct 3 - Wed, Oct 7
Frontier Logo
11:26 am - 4:45 pm
BOS
-
BNA
6h 19m
1 stop
Frontier Logo
5:40 pm - 8:20 am
BNA
-
BOS
13h 40m
1 stop
$254Frontier
Booking Insights

KAYAK's insights & trends for Boston to Kentucky flights

Get data-powered insights and trends into flights from Boston to Kentucky to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Boston to Kentucky?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Boston to Kentucky departing in September.

Flight prices are below average for this route right now.

Flights to Kentucky from Boston usually cost between $357 and $522 in September.
The lowest price found in the past 5 days was $277 on American Airlines (Sep 5-Sep 8).

What is the cheapest Boston to Kentucky flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Kentucky from Boston found in the last 5 days was to Louisville, at $355 round-trip. The most popular route is from Boston (BOS) to Louisville (SDF), and the cheapest round-trip airline ticket found on this route in the last 5 days was $355.

What is the cheapest time of day to fly to Kentucky?

The average price for all round-trip flights from Boston to Kentucky depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Kentucky is generally in the evening, when round-trip flights cost $355 on average. Morning departures are around 28% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $456.

Can I save money by flying with a layover from Boston to Kentucky?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $429 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Kentucky, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Kentucky is December, when tickets cost $381 (return) on average. On the other hand, the most expensive months are April and June, when the average cost of round-trip tickets is $532 and $508 respectively.

What’s the cheapest day of the week to fly from Boston to Kentucky?

The average price of all round-trip flights from Boston to Kentucky clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Kentucky on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Boston to Kentucky. For your return ticket, we recommend flying on a Saturday and avoiding Sundays for the best deals.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Kentucky, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Kentucky, you should book around 3 weeks before departure, which saves you about 6% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low season

January

Cheapest flight

$47
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Boston to Knoxville

FAQs - booking Kentucky flights

  • How does KAYAK find such low prices on flights from Boston to Kentucky?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Kentucky.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Kentucky?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to Kentucky is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Kentucky?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Boston to Kentucky with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Kentucky?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Boston to Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Boston to Kentucky

 
See real verified KAYAK customer reviews for airlines flying from Boston to Kentucky. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Kentucky? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4228 reviews
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

8.0 ExcellentSean, Jul 2026
HOU - LGB
Read more Southwest reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

WiFi was not working and didn’t have a beverage service

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

The seats were a bit cramped and worn, but otherwise okay.

Since the flight wasn’t full, we had some extra room. Crew was great

Flight from Savannah arrived very late and we did not take off till 2 hours after scheduled departure!

It is usually very pleasant. Good service for the price, international flights are even better

Flight attendant was very poor in taking care or showing attention. I slept up front for a few and missed the snacks. She saw me many times, went by me many times and never once asked if I needed anything. The whole 2 hours flight. And this is to a Diamond member in first.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

It’s always a great time flying with united airlines.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

Horrific. We were delayed due a flight attendant stuck in traffic en route to the airport. Over 100 people were then stuck in Charolette. Then I ran to make my layover only to find that my connection didn’t have a plane anymore. Waited 2.5 hours without any updates. On the flight we had to beg for even a pretzel option.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

Great experience. Good dinner and service. FA's were very nice and attentive.

Everything was fine. Flight boarded and departed on time. Seating was spacious enough for my carryon to fit under the seat in front of me. No complaints at all. Flight even arrived early.

Boston ticket agent Cheryl Porter is WONDERFUL. Our Iberia flight to Barcelona was cancelled the morning we were scheduled to leave and Cheryl was our super hero - she found us seats on a flight to London and on to Barcelona. Truly a “can-do” attitude which we appreciated so much after the Iberia ticket agents told us there was “absolutely nothing they could do”. (As did the customer service agents at Iberia’s call center) Ms Porter is truly a wonderful person who genuinely cares about travelers!

Everything you need to know for your flight from Boston to Kentucky

Information on your arrival and departure airports