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$97+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SDF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Oakland to Kentucky

Keep the following information in mind while searching for Oakland to Kentucky flight deals. Data was last updated September 11, 2025.

Round-trip from

$252
(Southwest)

One-way from

$97
(CheapOair)

Popular in

December

Cheapest in

October

Average price

$365
From Oakland to Kentucky
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One-way flight from Oakland to Kentucky
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Highest demand for flights based on searches. 7% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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.
Tue 11/1111:05 amOAK - BNA
1 stop6h 55mSouthwest
Sat 11/159:15 amBNA - OAK
1 stop7h 10mSouthwest
Deal found 9/10$252
This KAYAK deal was found by Cheapflights users on 9/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:30 amOAK - CVG
1 stop8h 00mAlaska Airlines
Sat 11/156:30 pmCVG - OAK
1 stop8h 29mAlaska Airlines
Deal found 9/10$253
This Southwest deal was found by Cheapflights users on 9/10. 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.
Sat 12/136:00 amOAK - SDF
1 stop6h 50mSouthwest
Mon 12/151:50 pmSDF - OAK
1 stop7h 50mSouthwest
Deal found 9/10$263
This KAYAK deal was found by Cheapflights users on 9/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:30 amOAK - BNA
1 stop6h 01mSpirit Airlines
Tue 9/303:26 pmBNA - OAK
1 stop10h 06mSpirit Airlines
Deal found 9/9$265
This Southwest deal was found by Cheapflights users on 9/9. 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.
Fri 11/75:25 amOAK - SDF
1 stop8h 25mSouthwest
Tue 11/116:05 amSDF - OAK
2 stops9h 15mSouthwest
Deal found 9/9$266
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Thu 9/256:30 amOAK - BNA
2 stops25h 07mMultiple Airlines
Mon 9/298:42 pmBNA - OAK
1 stop28h 50mMultiple Airlines
Deal found 9/10$269
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:30 amOAK - BNA
1 stop6h 01mSpirit Airlines
Wed 10/13:26 pmBNA - OAK
1 stop10h 06mSpirit Airlines
Deal found 9/10$272
This Southwest deal was found by Cheapflights users on 9/9. 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 10/287:10 amOAK - BNA
2 stops7h 35mSouthwest
Wed 10/294:45 pmBNA - OAK
1 stop6h 30mSouthwest
Deal found 9/9$274
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:30 amOAK - BNA
1 stop11h 17mSpirit Airlines
Tue 9/303:26 pmBNA - OAK
1 stop10h 06mSpirit Airlines
Deal found 9/9$278
This KAYAK deal was found by Cheapflights users on 9/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:30 amOAK - BNA
1 stop6h 01mSpirit Airlines
Wed 10/13:26 pmBNA - OAK
1 stop10h 06mSpirit Airlines
Deal found 9/9$282
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 12/1111:00 amOAK - CVG
1 stop6h 35mSouthwest
Mon 12/156:55 pmCVG - OAK
1 stop6h 25mSouthwest
Deal found 9/9$282
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:40 amOAK - CVG
1 stop8h 09mAlaska Airlines
Wed 10/226:49 pmCVG - OAK
1 stop8h 14mAlaska Airlines
Deal found 9/8$289

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 September 11, 2025.
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

OaklandNashville

OAK - BNA

OAKBNA

Oakland

Tue 11/11

11:05 am-8:00 pm

1 stop6h 55m

Nashville Intl

Sat 11/15

9:15 am-2:25 pm

1 stop7h 10m

$252

OaklandLouisville

OAK - SDF

OAKSDF

Oakland

Sat 12/13

6:00 am-3:50 pm

1 stop6h 50m

Louisville Intl

Mon 12/15

1:50 pm-6:40 pm

1 stop7h 50m

$263

OaklandLouisville

OAK - SDF

OAKSDF

Oakland

Fri 11/7

5:25 am-4:50 pm

1 stop8h 25m

Louisville Intl

Tue 11/11

6:05 am-12:20 pm

2 stops9h 15m

$266

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Sat 10/18

6:40 am-5:49 pm

1 stop8h 09m

Cincinnati Cinci./N. Kentucky

Wed 10/22

6:49 pm-12:03 am

1 stop8h 14m

$289

OaklandNashville

OAK - BNA

OAKBNA

Oakland

Sat 10/4

12:37 pm-9:51 pm

1 stop7h 14m

Nashville Intl

Wed 10/8

7:15 pm-11:53 pm

1 stop6h 38m

$297

OaklandLouisville

OAK - SDF

OAKSDF

Oakland

Sat 11/8

5:00 pm-9:51 am

2 stops13h 51m

Louisville Intl

Tue 11/11

6:03 pm-12:03 am

2 stops9h 00m

$307

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Tue 3/3

6:30 am-5:10 pm

1 stop7h 40m

Cincinnati Cinci./N. Kentucky

Wed 3/4

8:00 am-7:14 pm

2 stops14h 14m

$309

OaklandNashville

OAK - BNA

OAKBNA

Oakland

Fri 10/3

12:37 pm-9:51 pm

1 stop7h 14m

Nashville Intl

Wed 10/8

7:15 pm-11:53 pm

1 stop6h 38m

$309

OaklandNashville

OAK - BNA

OAKBNA

Oakland

Sat 10/4

12:37 pm-9:51 pm

1 stop7h 14m

Nashville Intl

Mon 10/6

7:15 pm-11:53 pm

1 stop6h 38m

$309

OaklandLouisville

OAK - SDF

OAKSDF

Oakland

Thu 12/4

12:35 pm-9:30 pm

1 stop5h 55m

Louisville Intl

Mon 12/8

1:05 pm-8:35 pm

1 stop10h 30m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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, January is the cheapest month in which you can book a flight from Oakland, California to Kentucky (average of $299). Flying from Oakland, California to Kentucky in April is currently the most expensive (average of $369). 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 OAK to KY?

Find hourly flight availability from Oakland to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

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

How much does it cost to fly round-trip from Oakland, California to Kentucky?

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 September 11, 2025.
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
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 6h 55m. Your travel time can differ by up to 1h 14m. The distance from Oakland, California to Kentucky is about 1953 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Oakland, California to Kentucky one-way?

    The cheapest airlines for a one-way flight from Oakland, California to Kentucky are Spirit Airlines ($97), Southwest ($123), and Alaska Airlines ($142).

  • 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, January is the cheapest month in which you can book a flight from Oakland, California to Kentucky (average of $299). Flying from Oakland, California to Kentucky in April is currently the most expensive (average of $369). 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

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$306Average$471FlexibilityNo cancel feeOn-time63%

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