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Key West

$475+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — EYW
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
1 adult, Economy
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Cheap flight deals from Oakland to Key West

Cheapest flights from Oakland to Key West
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 March 17, 2026.

This Delta deal was found by Cheapflights users on 3/16. 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 5/85:05 pm
OAK
-
EYW
2 stops14h 48m
Delta
Mon 5/117:30 am
EYW
-
OAK
2 stops19h 27m
Delta
Deal found 3/16$816
This Delta deal was found by Cheapflights users on 3/16. 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 5/75:05 pm
OAK
-
EYW
2 stops21h 18m
Delta
Mon 5/117:30 am
EYW
-
OAK
2 stops19h 27m
Delta
Deal found 3/16$871
This Delta deal was found by Cheapflights users on 3/16. 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 5/85:05 pm
OAK
-
EYW
2 stops14h 48m
Delta
Sun 5/106:19 pm
EYW
-
OAK
2 stops32h 38m
Delta
Deal found 3/16$945
This Delta deal was found by Cheapflights users on 3/14. 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 5/235:55 pm
OAK
-
EYW
2 stops13h 58m
Delta
Thu 5/286:19 pm
EYW
-
OAK
2 stops25h 06m
Delta
Deal found 3/14$948
This Delta deal was found by Cheapflights users on 3/16. 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 5/75:05 pm
OAK
-
EYW
2 stops23h 44m
Delta
Sun 5/106:19 pm
EYW
-
OAK
2 stops32h 38m
Delta
Deal found 3/16$1,001
This Delta deal was found by Cheapflights users on 3/15. 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.
Wed 4/225:55 am
OAK
-
EYW
2 stops10h 45m
Delta
Mon 4/272:40 pm
EYW
-
OAK
2 stops12h 14m
Delta
Deal found 3/15$1,167
This Delta deal was found by Cheapflights users on 3/14. 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 5/235:55 pm
OAK
-
EYW
2 stops13h 58m
Delta
Fri 5/297:30 am
EYW
-
OAK
2 stops11h 55m
Delta
Deal found 3/14$1,177
This Delta deal was found by Cheapflights users on 3/13. 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 4/94:49 pm
OAK
-
EYW
2 stops14h 59m
Delta
Tue 4/147:33 am
EYW
-
OAK
2 stops11h 51m
Delta
Deal found 3/13$1,197
This Delta deal was found by Cheapflights users on 3/14. 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.
Sun 5/245:55 pm
OAK
-
EYW
2 stops13h 58m
Delta
Thu 5/282:00 pm
EYW
-
OAK
2 stops12h 57m
Delta
Deal found 3/14$1,237
This Delta deal was found by Cheapflights users on 3/17. 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.
Wed 4/15:55 am
OAK
-
EYW
2 stops10h 46m
Delta
Sun 4/57:30 am
EYW
-
OAK
2 stops11h 30m
Delta
Deal found 3/17$1,260

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 March 17, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$816
(Delta)

One-way from

$475
(Delta)

Popular in

December

Cheapest in

August

Average price

$616
Provider with most accurate pricing for Oakland-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Key West flights.
Search Deals
From Oakland to Key West
Search Deals
One-way flight from Oakland to Key West
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($127 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 17, 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

Price

Cheapest round-trip

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Fri 5/8

5:05 pm-10:53 am

2 stops14h 48m

Key West

Mon 5/11

7:30 am-11:57 pm

2 stops19h 27m

$816

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Thu 5/7

5:05 pm-5:23 pm

2 stops21h 18m

Key West

Mon 5/11

7:30 am-11:57 pm

2 stops19h 27m

$871

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Thu 5/7

5:05 pm-7:49 pm

2 stops23h 44m

Key West

Sun 5/10

6:19 pm-11:57 pm

2 stops32h 38m

$1,001

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Wed 4/22

5:55 am-7:40 pm

2 stops10h 45m

Key West

Mon 4/27

2:40 pm-11:54 pm

2 stops12h 14m

$1,167

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Thu 4/9

4:49 pm-10:48 am

2 stops14h 59m

Key West

Tue 4/14

7:33 am-4:24 pm

2 stops11h 51m

$1,197
Quickest round-trip

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Wed 4/1

5:55 am-7:41 pm

2 stops10h 46m

Key West

Sun 4/5

7:30 am-4:00 pm

2 stops11h 30m

$1,260

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Sat 4/25

5:55 pm-10:46 am

2 stops13h 51m

Key West

Sat 5/2

11:45 am-9:41 pm

2 stops12h 56m

$1,439

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Sat 5/23

5:55 pm-10:53 am

2 stops13h 58m

Key West

Wed 5/27

7:30 am-4:25 pm

2 stops11h 55m

$1,499

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Fri 5/22

6:00 am-7:49 pm

2 stops10h 49m

Key West

Thu 5/28

2:00 pm-11:57 pm

2 stops12h 57m

$1,697

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Fri 5/22

5:05 pm-10:53 am

2 stops14h 48m

Key West

Fri 5/29

7:30 am-4:25 pm

2 stops11h 55m

$1,697

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/15

Showing 1-10 of 11 resultsSorted by cheapest first
1
2
  • 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.

Cheapflights Insights

Everything you need to know about your flight from Oakland to Key West

What is the cheapest month to book a flight from Oakland, California to Key West?

Currently, August is the cheapest month in which you can book a flight from Oakland, California to Key West (average of $227). Flying from Oakland, California to Key West in September is currently the most expensive (average of $501). 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.

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.

  • How long is the flight from Oakland, California to Key West?

    Airlines like Delta fly from Oakland, California to Key West in about 14h 48m. The time it takes to get you to your destination can typically vary by up to . The distance from Oakland, California to Key West is about 2535 mi.

  • Can I find deals for flights from Oakland to Key West that include hotel bookings?

    Yes. In addition to deals on Oakland to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Key West.

  • Can I find deals for business class flights from Oakland to Key West?

    Yes. Cheapflights offers flight deals from Oakland to Key West 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 Key West?

    Currently, August is the cheapest month in which you can book a flight from Oakland, California to Key West (average of $227). Flying from Oakland, California to Key West in September is currently the most expensive (average of $501). 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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