$645+ Cheap flights from Oakland, CA to Key West (OAK - EYW)
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 3/22. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — EYW
Feb 27 — Mar 61
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Oakland to Key West with Cheapflights
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 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 January 28, 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 January 28, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:55 am
OAK
- EYW
2 stops10h 47m
Delta
Wed 3/47:10 am
EYW
- OAK
2 stops12h 02m
Delta
Deal found 1/27![Delta logo]()
$1,380
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:55 am
OAK
- EYW
2 stops10h 47m
Delta
Wed 3/47:10 am
EYW
- OAK
2 stops12h 02m
Delta
Deal found 1/27![Delta logo]()
$1,440
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:55 am
OAK
- EYW
2 stops10h 47m
Delta
Sat 2/2811:59 am
EYW
- OAK
2 stops12h 47m
Delta
Deal found 1/26![Delta logo]()
$1,500
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 January 28, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $1,380 (Delta) |
One-way from | $645 (Delta) |
Popular in | December |
Cheapest in | August |
Average price | $423 |
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 January 28, 2026.
Use the filters below to find and compare flights from Oakland to Key West that are best for you.
Fly from
Oakland
Fly to
Key West
Route
Depart
Return
Price
OaklandKey West
OAK - EYW
OAKEYW
Oakland
Fri 2/27
5:55 am-7:42 pm
2 stops10h 47m
Key West
Wed 3/4
7:10 am-4:12 pm
2 stops12h 02m
$1,380
OaklandKey West
OAK - EYW
OAKEYW
Oakland
Thu 2/26
5:55 am-7:42 pm
2 stops10h 47m
Key West
Wed 3/4
7:10 am-4:12 pm
2 stops12h 02m
$1,440
OaklandKey West
OAK - EYW
OAKEYW
Oakland
Sat 2/21
5:55 am-7:42 pm
2 stops10h 47m
Key West
Sat 2/28
11:59 am-9:46 pm
2 stops12h 47m
$1,500
OaklandKey West
OAK - EYW
OAKEYW
Oakland
Sun 3/22
4:49 pm-10:48 am
2 stops14h 59m
$645
- 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.
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.