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Kentucky

$134+ Cheap flights from Oakland, CA (OAK) to Kentucky

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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SDF
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap flight deals from Oakland to Kentucky

Cheapest flights from Oakland to Kentucky
Explore the most affordable flight options available from Oakland to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:31 pm
OAK
-
CVG
1 stop24h 08m
Alaska Airlines
Wed 3/48:09 am
CVG
-
OAK
1 stop11h 28m
Alaska Airlines
Deal found 1/26$257
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:15 am
OAK
-
BNA
1 stop15h 44m
Alaska Airlines
Tue 3/33:54 pm
BNA
-
OAK
1 stop8h 55m
Alaska Airlines
Deal found 1/27$277
This CheapOair deal was found by Cheapflights users on 1/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:40 pm
OAK
-
CVG
1 stop20h 49m
Alaska Airlines
Tue 4/217:29 pm
CVG
-
OAK
1 stop16h 44m
Alaska Airlines
Deal found 1/25$277
This Delta deal was found by Cheapflights users on 1/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:55 am
OAK
-
CVG
1 stop5h 53m
Delta
Tue 5/53:00 pm
CVG
-
OAK
2 stops11h 54m
Delta
Deal found 1/25$302
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:15 am
OAK
-
BNA
1 stop15h 44m
Alaska Airlines
Tue 3/177:00 am
BNA
-
OAK
1 stop11h 37m
Alaska Airlines
Deal found 1/26$309
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:00 am
OAK
-
CVG
1 stop8h 29m
Alaska Airlines
Mon 4/207:29 pm
CVG
-
OAK
1 stop18h 04m
Alaska Airlines
Deal found 1/26$315
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:09 pm
OAK
-
BNA
1 stop7h 50m
Alaska Airlines
Tue 4/287:05 am
BNA
-
OAK
1 stop8h 10m
Alaska Airlines
Deal found 1/28$317
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:15 am
OAK
-
BNA
1 stop15h 44m
Alaska Airlines
Mon 3/25:53 pm
BNA
-
OAK
1 stop17h 31m
Alaska Airlines
Deal found 1/28$320
This Southwest deal was found by Cheapflights users on 1/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:55 am
OAK
-
CVG
2 stops9h 20m
Southwest
Mon 5/118:20 pm
CVG
-
OAK
1 stop7h 05m
Southwest
Deal found 1/26$320
This Southwest deal was found by Cheapflights users on 1/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:15 am
OAK
-
CVG
1 stop5h 55m
Southwest
Sun 3/16:25 am
CVG
-
OAK
1 stop7h 25m
Southwest
Deal found 1/26$326
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:15 am
OAK
-
CVG
1 stop11h 24m
Alaska Airlines
Tue 2/248:09 am
CVG
-
OAK
1 stop11h 28m
Alaska Airlines
Deal found 1/27$333
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:00 am
OAK
-
CVG
1 stop8h 29m
Alaska Airlines
Wed 4/17:29 pm
CVG
-
OAK
1 stop31h 14m
Alaska Airlines
Deal found 1/26$335

Find flight deals from Oakland to Kentucky

Keep the following information in mind while searching for Oakland to Kentucky flight deals. Data was last updated January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(CheapOair)

One-way from

$134
(Southwest)

Popular in

December

Cheapest in

August

Average price

$648
Provider with most accurate pricing for San Francisco-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Louisville Intl flights.
Search Deals
From Oakland to Kentucky
Search Deals
One-way flight from Oakland to Kentucky
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($104 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Kentucky 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 January 28, 2026.
Use the filters below to find and compare flights from Oakland to Kentucky that are best for you.

Fly from

Oakland

Fly to

Kentucky

Route

Depart

Return

Price

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Sat 5/2

11:55 pm-3:20 pm

1 stop12h 25m

Cincinnati Cinci./N. Kentucky

Tue 5/5

7:35 pm-11:25 pm

1 stop6h 50m

$310

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Wed 5/6

5:50 am-3:00 pm

1 stop6h 10m

Cincinnati Cinci./N. Kentucky

Mon 5/11

8:20 pm-12:25 am

1 stop7h 05m

$315

OaklandNashville

OAK - BNA

OAKBNA

Oakland

Sat 4/25

2:09 pm-11:59 pm

1 stop7h 50m

Nashville Intl

Wed 4/29

7:05 am-1:15 pm

1 stop8h 10m

$317

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Thu 3/19

5:45 am-3:35 pm

1 stop6h 50m

Cincinnati Cinci./N. Kentucky

Tue 3/24

7:35 pm-11:40 pm

1 stop7h 05m

$326

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Mon 3/9

5:55 am-2:52 pm

1 stop5h 57m

Cincinnati Cinci./N. Kentucky

Mon 3/23

7:59 pm-11:46 pm

1 stop6h 47m

$333

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Sat 2/21

6:15 am-8:39 pm

1 stop11h 24m

Cincinnati Cinci./N. Kentucky

Tue 2/24

8:09 am-4:37 pm

1 stop11h 28m

$333

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Wed 3/4

9:54 am-8:39 pm

1 stop7h 45m

Cincinnati Cinci./N. Kentucky

Sat 3/7

8:09 am-4:37 pm

1 stop11h 28m

$333

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Tue 3/31

7:00 am-6:29 pm

1 stop8h 29m

Cincinnati Cinci./N. Kentucky

Wed 4/1

7:29 pm-11:43 pm

1 stop31h 14m

$335

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Thu 2/12

5:55 am-3:11 pm

1 stop6h 16m

Cincinnati Cinci./N. Kentucky

Tue 2/17

8:12 am-11:55 am

1 stop6h 43m

$336

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Wed 3/25

5:55 am-2:52 pm

1 stop5h 57m

Cincinnati Cinci./N. Kentucky

Fri 3/27

8:05 am-11:51 am

1 stop6h 46m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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

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

What is the cheapest month to book a flight from Oakland, California to Kentucky?

Currently, September is the cheapest month in which you can book a flight from Oakland, California to Kentucky (average of $112). Flying from Oakland, California to Kentucky in January is currently the most expensive (average of $358). 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.

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kentucky. Reviews last updated January 28, 2026.
Get a feel of what it's like to fly with Southwest from Oakland to Kentucky by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Related info for your journey

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

    Oakland (OAK) is the airport you will fly out of if you book a flight from Oakland to Kentucky. It is only a 7.0 mi journey to Oakland (OAK) from Oakland’s city center.

  • How long is the flight from Oakland, California to Kentucky?

    Southwest, Alaska Airlines, and Delta can get you from Oakland, California to Kentucky in just under 7h 50m. Your travel time can differ by up to 5h 39m. The distance from Oakland, California to Kentucky is about 1953 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Oakland, California to Kentucky?

    Most travelers choose Oakland - Nashville Intl, Oakland - Cincinnati Cinci./N. Kentucky or Oakland - Louisville Intl when deciding on the best route from Oakland, California to Kentucky.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Kentucky 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 Oakland, California to Kentucky?

    Currently, September is the cheapest month in which you can book a flight from Oakland, California to Kentucky (average of $112). Flying from Oakland, California to Kentucky in January is currently the most expensive (average of $358). 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

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Alternative routes for Oakland to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Oakland to Kentucky

Discover the top airline that operate flights from Oakland to Kentucky. 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$348Average$474FlexibilityNo cancel feeOn-time63%

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