In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

How far in advance should I book a flight from Oakland, California to Key West?

To save on the cost of your flight from Oakland, California to Key West, book at least 51 days before your planned departure. Booking around this time can save you about 101% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $355 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $1,009.

What is the cheapest month to fly from Oakland, California to Key West?

August is one of the best times of the year to fly to Key West from Oakland, California. Prices for August average $474 per person but you can even find prices for as low as $227. The most expensive prices can be found in the month of June. Opting for a August flight can save you 40% on your journey compared to booking in June

What is the cheapest time of day to fly from OAK to EYW?

When flying from Oakland, California to Key West, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 8% versus a flight in the morning.

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.

$495+ Flights from Oakland, CA to Key West

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Cheap flight deals from Oakland to Key West

Round-trip from	$495 (Mytrip)
One-way from	$380 (Mytrip)
Popular in	June
Cheapest in	August
Average price	$383

From Oakland to Key West

Search Deals

One-way flight from Oakland to Key West

Search Deals

Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Find 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 July 30, 2025.

Fri 9/196:00 amOAK - EYW

3 stops24h 02mMultiple Airlines

Mon 9/2212:32 pmEYW - OAK

2 stops22h 06mMultiple Airlines

Deal found 7/29

$495

Fri 9/195:05 pmOAK - EYW

2 stops14h 50mDelta

Mon 9/222:00 pmEYW - OAK

2 stops12h 50mDelta

Deal found 7/29

$1,059

Best flights from Oakland to Key West
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 July 30, 2025.

Fri 9/196:00 amOAK - EYW

3 stops24h 02mMultiple Airlines

Mon 9/2212:32 pmEYW - OAK

2 stops22h 06mMultiple Airlines

Deal found 7/29

$495

Fri 9/195:05 pmOAK - EYW

2 stops14h 50mDelta

Mon 9/222:00 pmEYW - OAK

2 stops12h 50mDelta

Deal found 7/29

$1,059

Last-minute flights from Oakland to Key West
Discover last-minute flight deals from Oakland to Key West. Data last updated July 30, 2025 and is based on user searches.

Sat 8/26:00 amOAK - EYW

3 stops28h 07mMultiple Airlines

Fri 8/810:02 amEYW - OAK

2 stops25h 26mMultiple Airlines

Deal found 7/28

$853

Fly from

Fly to

Route

Depart

Return

Price

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Fri 9/19

6:00 am-9:02 am

3 stops24h 02m

Key West

Mon 9/22

12:32 pm-7:38 am

2 stops22h 06m

$495

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Fri 9/19

5:05 pm-10:55 am

2 stops14h 50m

Key West

Mon 9/22

2:00 pm-11:50 pm

2 stops12h 50m

$1,059

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 $328). Flying from Oakland, California to Key West in March is currently the most expensive (average of $492). 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.

Reviews of airlines servicing Key West

See what other customers who have flown with Delta from Oakland to Key West have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,980 reviews

Reviews

1 / 20

10.0

Excellent

Michael,Sep 2023

SMF - ATL

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Delta

8.0

Very good

7,980 reviews

Delta

8.0

Very good

7,980 reviews

Reviews

1 / 20

10.0

Excellent

Michael,Sep 2023

SMF - ATL

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Related info for your journey

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 $328). Flying from Oakland, California to Key West in March is currently the most expensive (average of $492). 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

Browse thousands of different options on Cheapflights for your next trip

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$495+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Oakland to Key West with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Oakland to Key West

Round-trip from

One-way from

Popular in

Cheapest in

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Find 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 July 30, 2025.

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 July 30, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Oakland to Key West that are best for you.

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.

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?

Reviews of airlines servicing Key West

See what other customers who have flown with Delta from Oakland to Key West have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

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.

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oakland to Key West

See prices for flight routes from nearby airports that may be better suited for you.

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Travel Smart

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 July 30, 2025.