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Key West

$474+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — EYW
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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 December 15, 2025.

This Delta deal was found by Cheapflights users on 12/14. 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.
Thu 12/255:53 amOAK - EYW
2 stops10h 50mDelta
Tue 12/307:25 amEYW - OAK
2 stops11h 39mDelta
Deal found 12/14$1,359

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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,359
(Delta)

One-way from

$474
(Delta)

Popular in

December

Cheapest in

August

Average price

$747
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. 20% potential increase in price ($128 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 15, 2025.
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

Thu 12/25

5:53 am-7:43 pm

2 stops10h 50m

Key West

Tue 12/30

7:25 am-4:04 pm

2 stops11h 39m

$1,359

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Fri 2/6

5:55 am-7:40 pm

2 stops10h 45m

Key West

Mon 2/9

2:45 pm-11:53 pm

2 stops12h 08m

$3,953

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Wed 1/28

5:55 am-7:40 pm

2 stops10h 45m

$474

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Wed 1/28

7:33 pm-1:30 pm

3 stops38h 57m

$628

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Sun 12/28

5:53 am-8:58 pm

2 stops12h 05m

$935

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Compare providers for flights from Oakland to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oakland to Key West in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oakland, California-Key West flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Oakland, California-Key West flight deals on Cheapflights vs. eDreams >95% 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 eDreams the most. eDreams 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 10h 50m. 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.

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