$164+ Cheap flights from Oakland, CA (OAK) to Kentucky
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SDF
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Oakland to KentuckyExplore 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 November 4, 2026.
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 November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/1. 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 12/25:30 am -
1 stop8h 40m
Fri 12/47:35 pm -
1 stop7h 00m
Deal found 11/1![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 11/1. 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.
Wed 12/25:07 pm -
2 stops13h 01m
Fri 12/43:12 pm -
2 stops11h 51m
Deal found 11/1![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 11/2. 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 11/1711:50 pm -
1 stop7h 40m
Sat 11/218:30 pm -
1 stop6h 55m
Deal found 11/2![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 11/4. 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 12/16:45 am -
1 stop7h 25m
Thu 12/107:35 pm -
1 stop7h 00m
Deal found 11/4![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 11/2. 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 12/311:40 pm -
1 stop6h 15m
Sat 1/28:30 pm -
1 stop13h 20m
Deal found 11/2![Southwest logo]()
$488
Best flights from Oakland to KentuckyDiscover carefully curated flight deals from Oakland to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Oakland to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/4. 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.
Mon 12/146:30 am -
1 stop6h 05m
Tue 12/157:35 pm -
1 stop7h 00m
Deal found 11/4![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 11/1. 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.
Wed 12/25:07 pm -
2 stops13h 01m
Fri 12/43:12 pm -
2 stops11h 51m
Deal found 11/1![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 11/1. 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 12/25:30 am -
1 stop8h 40m
Fri 12/47:35 pm -
1 stop7h 00m
Deal found 11/1![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 11/3. 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 1/81:45 pm -
1 stop6h 05m
Mon 1/116:40 am -
2 stops8h 35m
Deal found 11/3![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 11/4. 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 12/16:45 am -
1 stop7h 25m
Thu 12/107:35 pm -
1 stop7h 00m
Deal found 11/4![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 11/3. 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 2/239:10 am -
2 stops8h 05m
Sun 2/287:00 am -
2 stops9h 20m
Deal found 11/3![Southwest logo]()
$463
This Southwest deal was found by Cheapflights users on 11/2. 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 12/3111:50 pm -
1 stop7h 40m
Sat 1/29:50 pm -
2 stops12h 00m
Deal found 11/2![Southwest logo]()
$494
This Southwest deal was found by Cheapflights users on 10/31. 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 4/67:40 am -
2 stops8h 45m
Sun 4/116:30 am -
2 stops11h 55m
Deal found 10/31![Southwest logo]()
$529
Last-minute flights from Oakland to KentuckyDiscover last-minute flight deals from Oakland to Kentucky. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Kentucky. Data last updated November 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/2. 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 11/1711:50 pm -
1 stop7h 40m
Sat 11/218:30 pm -
1 stop6h 55m
Deal found 11/2![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 11/4. 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 12/16:45 am -
1 stop7h 25m
Thu 12/107:35 pm -
1 stop7h 00m
Deal found 11/4![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 11/1. 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 12/25:30 am -
1 stop8h 40m
Fri 12/47:35 pm -
1 stop7h 00m
Deal found 11/1![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 11/1. 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.
Wed 12/25:07 pm -
2 stops13h 01m
Fri 12/43:12 pm -
2 stops11h 51m
Deal found 11/1![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 11/2. 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 12/311:40 pm -
1 stop6h 15m
Sat 1/28:30 pm -
1 stop13h 20m
Deal found 11/2![Southwest logo]()
$488
One-way flights from Oakland to KentuckySearch for one-way flight options from Oakland to Kentucky. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Oakland to Kentucky. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/3. 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 2/245:50 am -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$164
This Delta deal was found by Cheapflights users on 11/3. 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 12/115:55 am -
2 stops11h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 11/1. 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.
Mon 11/1611:50 pm -
1 stop7h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 11/1. 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.
Sun 11/1511:50 pm -
1 stop7h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$174
This Delta deal was found by Cheapflights users on 10/31. 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 11/145:55 am -
2 stops9h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Delta logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 2/2410:58 pm -
3 stops39h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 10/31. 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 11/145:10 am -
1 stop6h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 11/3. 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 12/118:30 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 11/1. 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 11/165:55 am -
2 stops8h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 11/4. 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 12/185:00 am -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Fri 12/1112:28 pm -
3 stops25h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$296
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $327 (Southwest) |
One-way from | $164 (Southwest) |
Popular in | December |
Cheapest in | August |
Average price | $383 |
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 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Oakland to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Fri 12/11
5:55 am-8:54 pm
2 stops11h 59m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$169
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Sun 11/15
11:50 pm-10:30 am
1 stop7h 40m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$174
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Sat 11/14
5:55 am-6:20 pm
2 stops9h 25m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$179
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Wed 11/18
5:55 am-5:17 pm
2 stops8h 22m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$179
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Sat 11/14
5:10 am-2:20 pm
1 stop6h 10m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$200
Quickest round-trip
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Fri 12/11
8:30 am-5:30 pm
1 stop6h 00m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$210
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Mon 11/16
5:55 am-5:17 pm
2 stops8h 22m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$265
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Fri 12/18
5:00 am-5:00 pm
2 stops9h 00m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$268
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Mon 12/14
6:30 am-3:35 pm
1 stop6h 05m
Louisville Intl
Tue 12/15
7:35 pm-11:35 pm
1 stop7h 00m
$327
OaklandLouisville
OAK Oakland - SDF Louisville Intl
OAKSDF
Oakland
Wed 12/2
5:30 am-5:10 pm
1 stop8h 40m
Louisville Intl
Fri 12/4
7:35 pm-11:35 pm
1 stop7h 00m
$327
Showing 1-10 of 19 resultsSorted by cheapest first
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.
OAK-SDF
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
OAK-USKY
OAK-SDF
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 $449). Flying from Oakland, California to Kentucky in February is currently the most expensive (average of $822). 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.
How much does it cost to fly round-trip from Oakland, California to Kentucky?
Airfare is below average for this route at the moment.
Oakland, California to Kentucky flights typically cost between $542 and $626 in December.The cheapest round-trip price found within the last 5 days was $327 on Southwest (Dec 2-Dec 4).
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 November 4, 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.
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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.
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Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
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Oakland and Kentucky flights
Browse other Oakland and Kentucky flight options. Last updated on November 4, 2026.
Popular flight searches
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Oakland to Kentucky flights
Consider these flights traveling from Oakland to Kentucky.
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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$306 | Average$576 | FlexibilityNo cancel fee | On-time63% |