$106 Find Cheap Flights from San Jose 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 San Jose to Kentucky departing on 8/24. 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.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from San Jose to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisville1 stop$411
Lexington
Lexington1 stop$379
Paducah
Paducah1 stop$572
Owensboro
Owensboro1 stop$633
Nashville
Nashville1 stop$249
Louisville
Louisville1 stop$411
Lexington
Lexington1 stop$379
Paducah
Paducah1 stop$572
Owensboro
Owensboro1 stop$633
Nashville
Nashville1 stop$249

Book Cheap San Jose 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 San Jose 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 San Jose to Kentucky

Thu, Oct 1 - Mon, Oct 12
Frontier Logo
10:47 pm - 1:04 pm
SJC
-
BNA
12h 17m
1 stop
Frontier Logo
7:42 pm - 8:08 pm
BNA
-
SJC
26h 26m
2 stops
$249Frontier
Thu, Oct 29 - Tue, Nov 10
Frontier Logo
2:24 pm - 1:58 pm
SJC
-
BNA
21h 34m
1 stop
Frontier Logo
7:42 pm - 1:12 pm
BNA
-
SJC
43h 30m
2 stops
$252Frontier
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
6:45 am - 1:00 pm
SJC
-
BNA
4h 15mnonstop
Southwest Logo
4:25 pm - 7:10 pm
BNA
-
SJC
4h 45mnonstop
$287Southwest
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
6:45 am - 1:00 pm
SJC
-
BNA
4h 15mnonstop
Southwest Logo
4:25 pm - 7:10 pm
BNA
-
SJC
4h 45mnonstop
$287Southwest
Sat, Aug 29 - Sat, Sep 5
Delta Logo
6:40 am - 3:56 pm
SJC
-
BNA
7h 16m
1 stop
Delta Logo
5:14 am - 11:28 am
BNA
-
SJC
8h 14m
1 stop
$307Delta
Tue, Oct 13 - Wed, Oct 21
Delta Logo
12:51 pm - 9:51 pm
SJC
-
BNA
7h 00m
1 stop
Delta Logo
6:43 am - 2:13 pm
BNA
-
SJC
9h 30m
1 stop
$307Delta
Tue, Oct 6 - Tue, Oct 13
American Airlines Logo
6:00 am - 5:16 pm
SJC
-
BNA
9h 16m
1 stop
American Airlines Logo
4:51 pm - 10:08 pm
BNA
-
SJC
7h 17m
1 stop
$307American Airlines
Sat, Sep 26 - Tue, Sep 29
American Airlines Logo
6:00 am - 5:22 pm
SJC
-
BNA
9h 22m
1 stop
American Airlines Logo
4:55 pm - 10:01 pm
BNA
-
SJC
7h 06m
1 stop
$307American Airlines
Wed, Aug 26 - Sat, Aug 29
United Airlines Logo
8:45 am - 8:33 pm
SJC
-
BNA
9h 48m
2 stops
United Airlines Logo
12:33 pm - 8:57 pm
BNA
-
SJC
10h 24m
2 stops
$317United Airlines
Sat, Sep 5 - Tue, Sep 15
United Airlines Logo
2:10 pm - 11:55 pm
SJC
-
CVG
6h 45m
1 stop
United Airlines Logo
6:08 pm - 10:50 pm
CVG
-
SJC
7h 42m
1 stop
$323United Airlines
Booking Insights

KAYAK's insights & trends for San Jose to Kentucky flights

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

What is the cheapest month to fly from San Jose to Kentucky?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose 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 San Jose to Kentucky is February, when tickets cost $476 (return) on average. On the other hand, the most expensive months are June and April, when the average cost of round-trip tickets is $904 and $823 respectively.

Good to know

Low season

January

Cheapest flight

$106
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 30% increase in price.
Flight from San Jose to Nashville

FAQs - booking Kentucky flights

  • How does KAYAK find such low prices on flights from San Jose 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 San Jose to Kentucky.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Jose 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 San Jose 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 San Jose 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 San Jose 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 San Jose 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 3 airlines serving from San Jose to Kentucky

 
See real verified KAYAK customer reviews for airlines flying from San Jose 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 San Jose 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 4227 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

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

6.0 GoodGordon, Jul 2026
SAN - MCO
Read more Southwest reviews

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

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

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

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Forget beverage, they didn't even have water for half the passangers?

Flight was not full! Had a whole row to myself.

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

Wifi didn’t work, no service, seats are hard as rocks

Delta is always late. Ruined our first day of a short vacation. Timing is important. We pay to stay on an itinerary

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

Flight team was great and we even arrived ahead of plan!

First The flight got delayed because one of the crew members was late and we couldn’t board until she arrived. Then we all boarded and got held in the tarmac for another 30 min.

Crew was absolutely fantastic and we’re so welcoming and friendly ❤️

It was as good as it could be. Flying is not a pleasant experience these days.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

Flight was late, the only reason I almost missed my flight was that my connection was also late.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

It was a short, comfortable flight. It did leave an hour late due to the pilot having to be replaced (family emergency) but that didn’t inconvenience myself & my friend. The situation was explained, eventually.

UA594 was delayed multiple times. I ended up getting picked up so I can make it in time for work 6AM on Monday, 7/6/2026

Boarded from a very small gate at LAX. Staff at gate had us line up, then waited 25 minutes to board without a word of explanation. Plane arrived on time then waited 20 minutes for a plane to vacate our gate. Majority of bags arrived after 15 minutes but it took an hour for a small number of remaining bags to be off-loaded despite my “priority” bag tag.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

A good, solid, no frills experience. Departed and arrived on time, staff were pleasant and attentive. Loved the Bluetooth connectivity on the SJC to IAH leg. Being able to watch movies and listen to them with my noise cancelling headphones was lovely. Missed that on the IAH to LHR leg (so I put the wired buds on and my over ear Quiet Comforts over those).

Everything you need to know for your flight from San Jose to Kentucky

Information on your arrival and departure airports