$1,139+ Cheap flights from Oakland, CA to Key West (OAK - EYW)
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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — EYW
Jul 18 — Jul 251
Round-trip
1 adult, Economy
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1. Tell us where you want to go
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Oakland to Key West
Cheapest
Best
Last-minute
Cheapest flights from Oakland to Key WestExplore the most affordable flight options available from Oakland to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2026.
Explore the most affordable flight options available from Oakland to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2026.
This Delta deal was found by Cheapflights users on 6/15. 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.
Sun 7/55:03 pm
OAK
- EYW
2 stops14h 50m
Delta
Sat 7/117:50 am
EYW
- OAK
2 stops11h 31m
Delta
Deal found 6/15![Delta logo]()
$1,139
This Delta deal was found by Cheapflights users on 6/14. 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 7/255:30 pm
OAK
- EYW
2 stops14h 30m
Delta
Sat 8/111:48 am
EYW
- OAK
2 stops12h 50m
Delta
Deal found 6/14![Delta logo]()
$1,337
This Delta deal was found by Cheapflights users on 6/17. 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 7/175:05 pm
OAK
- EYW
2 stops14h 45m
Delta
Fri 7/242:24 pm
EYW
- OAK
2 stops12h 26m
Delta
Deal found 6/17![Delta logo]()
$1,594
Best flights from Oakland to Key WestDiscover carefully curated flight deals from Oakland to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 18, 2026.
Discover carefully curated flight deals from Oakland to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 18, 2026.
This Delta deal was found by Cheapflights users on 6/15. 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.
Sun 7/55:03 pm
OAK
- EYW
2 stops14h 50m
Delta
Sat 7/117:50 am
EYW
- OAK
2 stops11h 31m
Delta
Deal found 6/15![Delta logo]()
$1,139
This Delta deal was found by Cheapflights users on 6/14. 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 7/255:30 pm
OAK
- EYW
2 stops14h 30m
Delta
Sat 8/111:48 am
EYW
- OAK
2 stops12h 50m
Delta
Deal found 6/14![Delta logo]()
$1,337
This Delta deal was found by Cheapflights users on 6/17. 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 7/175:05 pm
OAK
- EYW
2 stops14h 45m
Delta
Fri 7/242:24 pm
EYW
- OAK
2 stops12h 26m
Delta
Deal found 6/17![Delta logo]()
$1,594
Last-minute flights from Oakland to Key WestDiscover last-minute flight deals from Oakland to Key West. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Key West. Data last updated June 18, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/15. 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.
Sun 7/55:03 pm
OAK
- EYW
2 stops14h 50m
Delta
Sat 7/117:50 am
EYW
- OAK
2 stops11h 31m
Delta
Deal found 6/15![Delta logo]()
$1,139
This Delta deal was found by Cheapflights users on 6/17. 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 7/175:05 pm
OAK
- EYW
2 stops14h 45m
Delta
Fri 7/242:24 pm
EYW
- OAK
2 stops12h 26m
Delta
Deal found 6/17![Delta logo]()
$1,594
This Delta deal was found by Cheapflights users on 6/14. 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 7/255:30 pm
OAK
- EYW
2 stops14h 30m
Delta
Sat 8/111:48 am
EYW
- OAK
2 stops12h 50m
Delta
Deal found 6/14![Delta logo]()
$1,337
Find flight deals from Oakland to Key West
Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 18, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $1,139 (Delta) |
Popular in | December |
Cheapest in | July |
Average price | $651 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland to Key West 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 June 18, 2026.
Use the filters below to find and compare flights from Oakland to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
OaklandKey West
OAK - EYW
OAKEYW
Oakland
Sun 7/5
5:03 pm-10:53 am
2 stops14h 50m
Key West
Sat 7/11
7:50 am-4:21 pm
2 stops11h 31m
$1,139
OaklandKey West
OAK - EYW
OAKEYW
Oakland
Sat 7/25
5:30 pm-11:00 am
2 stops14h 30m
Key West
Sat 8/1
11:48 am-9:38 pm
2 stops12h 50m
$1,337
OaklandKey West
OAK - EYW
OAKEYW
Oakland
Fri 7/17
5:05 pm-10:50 am
2 stops14h 45m
Key West
Fri 7/24
2:24 pm-11:50 pm
2 stops12h 26m
$1,594
Sorted by cheapest first
- Most accurate provider: When it comes to deals on Oakland, California-Key West flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Oakland, California-Key West flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Oakland, California-Key West flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Oakland, California-Key West flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Oakland to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Oakland with our price prediction graph.
OAK-EYW
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.
Related info for your journey
Find useful and relevant information for your journey from Oakland to Key West. 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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