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Key West

$270+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — EYW
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
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 August 1, 2026.

This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:00 pm
OAK
-
EYW
2 stops14h 50m
Delta
Wed 9/21:59 pm
EYW
-
OAK
2 stops11h 39m
Delta
Deal found 7/29$577
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:33 pm
OAK
-
EYW
2 stops28h 24m
Delta
Tue 9/111:48 am
EYW
-
OAK
2 stops13h 50m
Delta
Deal found 7/29$593
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:00 pm
OAK
-
EYW
2 stops14h 50m
Delta
Wed 9/27:40 am
EYW
-
OAK
2 stops11h 34m
Delta
Deal found 7/29$617
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:33 pm
OAK
-
EYW
2 stops19h 17m
Delta
Wed 9/211:48 am
EYW
-
OAK
2 stops13h 50m
Delta
Deal found 7/29$624
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:33 pm
OAK
-
EYW
2 stops25h 47m
Delta
Wed 9/27:40 am
EYW
-
OAK
2 stops11h 34m
Delta
Deal found 7/29$628
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:33 pm
OAK
-
EYW
2 stops20h 53m
Delta
Tue 9/17:40 am
EYW
-
OAK
2 stops11h 34m
Delta
Deal found 7/29$638
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:00 pm
OAK
-
EYW
2 stops14h 50m
Delta
Fri 9/411:48 am
EYW
-
OAK
2 stops31h 26m
Delta
Deal found 7/29$671
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:33 pm
OAK
-
EYW
2 stops25h 47m
Delta
Wed 9/211:48 am
EYW
-
OAK
2 stops13h 50m
Delta
Deal found 7/29$678
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:33 pm
OAK
-
EYW
2 stops19h 17m
Delta
Fri 9/46:15 pm
EYW
-
OAK
2 stops24h 59m
Delta
Deal found 7/29$681
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:33 pm
OAK
-
EYW
2 stops19h 17m
Delta
Fri 9/41:59 pm
EYW
-
OAK
2 stops29h 15m
Delta
Deal found 7/29$691
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:00 pm
OAK
-
EYW
2 stops14h 50m
Delta
Mon 8/316:15 pm
EYW
-
OAK
2 stops31h 23m
Delta
Deal found 7/29$702
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:33 pm
OAK
-
EYW
2 stops28h 24m
Delta
Mon 8/316:15 pm
EYW
-
OAK
2 stops24h 59m
Delta
Deal found 7/29$713

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 August 1, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$577
(Delta)

One-way from

$270
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$494
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. 13% potential increase in price ($92 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 1, 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

Sat 8/29

12:33 pm-10:50 am

2 stops19h 17m

Key West

Wed 9/2

1:59 pm-10:38 pm

2 stops11h 39m

$593

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Thu 8/27

12:33 pm-5:20 pm

2 stops25h 47m

Key West

Wed 9/2

7:40 am-4:14 pm

2 stops11h 34m

$628

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Tue 8/25

5:00 pm-10:50 am

2 stops14h 50m

Key West

Fri 9/4

11:48 am-4:14 pm

2 stops31h 26m

$671

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Sat 12/5

5:00 pm-10:48 am

2 stops14h 48m

Key West

Fri 12/11

6:02 pm-4:17 pm

2 stops25h 15m

$760

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Wed 8/26

12:33 pm-7:57 pm

2 stops28h 24m

Key West

Mon 8/31

6:15 pm-4:14 pm

2 stops24h 59m

$763

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Wed 8/26

12:33 pm-7:57 pm

2 stops28h 24m

Key West

Sat 8/29

1:31 pm-10:38 pm

2 stops12h 07m

$798

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Fri 12/4

12:37 pm-8:02 pm

2 stops28h 25m

Key West

Fri 12/11

6:02 pm-11:56 am

2 stops20h 54m

$866

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Sat 12/5

12:37 pm-5:07 pm

2 stops25h 30m

Key West

Sat 12/12

6:02 pm-4:17 pm

2 stops25h 15m

$990

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Sat 10/17

5:02 pm-10:47 am

2 stops14h 45m

Key West

Sat 10/24

7:40 am-4:22 pm

2 stops11h 42m

$1,089

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Sun 8/16

5:00 pm-10:50 am

2 stops14h 50m

Key West

Thu 8/20

1:59 pm-11:56 pm

2 stops12h 57m

$1,102

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

Showing 1-10 of 18 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.

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 19h 17m. 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.

See more FAQs

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