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$145+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SDF
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$291
(Alaska Airlines)

One-way from

$145
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$398
Provider with most accurate pricing for San Francisco-Louisville Intl flight deals.
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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. 8% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 29, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:40 amOAK - CVG
1 stop7h 43mAlaska Airlines
Wed 12/106:23 pmCVG - OAK
1 stop8h 36mAlaska Airlines
Deal found 10/27$291
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:55 amOAK - CVG
1 stop6h 15mDelta
Wed 12/106:30 amCVG - OAK
2 stops12h 34mDelta
Deal found 10/27$295
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:50 pmOAK - CVG
2 stops22h 54mDelta
Wed 12/106:30 amCVG - OAK
2 stops12h 34mDelta
Deal found 10/27$299
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/912:30 pmOAK - CVG
1 stop7h 24mDelta
Sat 12/136:10 amCVG - OAK
2 stops8h 40mDelta
Deal found 10/27$302
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:51 pmOAK - CVG
2 stops22h 51mDelta
Wed 12/36:30 amCVG - OAK
2 stops12h 34mDelta
Deal found 10/27$304
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1812:28 pmOAK - CVG
1 stop7h 24mDelta
Wed 12/36:30 amCVG - OAK
2 stops12h 34mDelta
Deal found 10/27$306
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/94:50 pmOAK - CVG
2 stops13h 05mDelta
Wed 12/102:20 pmCVG - OAK
2 stops12h 48mDelta
Deal found 10/27$307
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:55 amOAK - CVG
1 stop6h 15mDelta
Mon 12/86:30 amCVG - OAK
2 stops12h 34mDelta
Deal found 10/27$310
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/62:31 pmOAK - BNA
1 stop22h 24mAlaska Airlines
Tue 12/95:45 pmBNA - OAK
1 stop17h 01mAlaska Airlines
Deal found 10/27$330
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/134:50 pmOAK - SDF
2 stops14h 00mDelta
Mon 12/153:16 pmSDF - OAK
2 stops11h 52mDelta
Deal found 10/28$338
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
Wed 12/102:31 pmOAK - BNA
1 stop7h 28mAlaska Airlines
Mon 12/155:45 pmBNA - OAK
1 stop17h 01mAlaska Airlines
Deal found 10/29$350
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 12/136:40 amOAK - BNA
1 stop30h 15mAlaska Airlines
Thu 2/125:15 pmBNA - OAK
1 stop8h 23mAlaska Airlines
Deal found 10/29$353

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 October 29, 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

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Sat 12/6

5:55 am-3:10 pm

1 stop6h 15m

Cincinnati Cinci./N. Kentucky

Wed 12/10

6:30 am-4:04 pm

2 stops12h 34m

$295

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Fri 12/5

4:50 pm-6:44 pm

2 stops22h 54m

Cincinnati Cinci./N. Kentucky

Sat 12/13

8:05 am-11:50 am

1 stop6h 45m

$300

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Fri 12/5

4:50 pm-6:44 pm

2 stops22h 54m

Cincinnati Cinci./N. Kentucky

Wed 12/10

7:59 pm-12:08 am

1 stop7h 09m

$300

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Tue 12/9

12:30 pm-10:54 pm

1 stop7h 24m

Cincinnati Cinci./N. Kentucky

Sat 12/13

6:10 am-11:50 am

2 stops8h 40m

$302

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Mon 12/8

4:50 pm-6:43 pm

2 stops22h 53m

Cincinnati Cinci./N. Kentucky

Sat 12/13

11:30 am-10:00 pm

2 stops13h 30m

$305

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Sat 12/6

5:55 am-3:10 pm

1 stop6h 15m

Cincinnati Cinci./N. Kentucky

Fri 12/12

6:30 am-12:08 am

2 stops20h 38m

$310

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Sat 12/6

4:50 pm-8:55 am

2 stops13h 05m

Cincinnati Cinci./N. Kentucky

Mon 12/8

6:30 am-12:08 am

2 stops20h 38m

$315

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Fri 12/5

6:40 am-5:23 pm

1 stop7h 43m

Cincinnati Cinci./N. Kentucky

Wed 12/10

6:23 pm-11:59 pm

1 stop8h 36m

$317

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Sat 12/6

12:30 pm-10:54 pm

1 stop7h 24m

Cincinnati Cinci./N. Kentucky

Thu 12/11

8:05 am-11:50 am

1 stop6h 45m

$317

OaklandCincinnati

OAK - CVG

OAKCVG

Oakland

Fri 12/5

4:50 pm-6:44 pm

2 stops22h 54m

Cincinnati Cinci./N. Kentucky

Mon 12/8

7:59 pm-12:08 am

1 stop7h 09m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 February is currently the most expensive (average of $299). 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 October 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Oakland, California to Kentucky at noon. If you’re flexible enough to do this you can expect to save up to 40% on your trip compared to booking a flight in the evening.

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 October 29, 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
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

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?

    Delta, Alaska Airlines, and Southwest can get you from Oakland, California to Kentucky in just under 6h 15m. Your travel time can differ by up to 2h 50m. The distance from Oakland, California to Kentucky is about 2020 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 Alaska Airlines ($145), Delta ($190), and Southwest ($218).

  • 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 February is currently the most expensive (average of $299). 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$348Average$476FlexibilityNo cancel feeOn-time63%

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