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Florida Keys

$109+ Cheap flights from Oakland, CA (OAK) to Florida Keys

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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — EYW
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheap flight deals from Oakland to Florida Keys

Keep the following information in mind while searching for Oakland to Florida Keys flight deals. Data was last updated November 6, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$217
(Southwest)

One-way from

$109
(Southwest)

Popular in

December

Cheapest in

January

Average price

$381
Provider with most accurate pricing for San Francisco-Miami flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Miami flights.
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From Oakland to Florida Keys
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One-way flight from Oakland to Florida Keys
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Highest demand for flights based on searches. 6% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Oakland to Florida Keys

Cheapest flights from Oakland to Florida Keys
Explore the most affordable flight options available from Oakland to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2025.

This Southwest deal was found by Cheapflights users on 11/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:45 amOAK - MIA
1 stop7h 15mSouthwest
Thu 12/111:05 pmMIA - OAK
1 stop8h 35mSouthwest
Deal found 11/5$217
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/39:45 amOAK - MIA
1 stop27h 15mAlaska Airlines
Sat 12/65:00 pmMIA - OAK
1 stop18h 46mAlaska Airlines
Deal found 11/4$251
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/179:45 amOAK - MIA
1 stop17h 27mAlaska Airlines
Thu 12/257:25 amMIA - OAK
1 stop19h 34mAlaska Airlines
Deal found 11/6$254
This Delta deal was found by Cheapflights users on 11/5. 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 12/94:50 pmOAK - MIA
1 stop10h 34mDelta
Wed 12/176:50 pmMIA - OAK
1 stop8h 18mDelta
Deal found 11/5$257
This Delta deal was found by Cheapflights users on 11/4. 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 12/34:50 pmOAK - MIA
1 stop10h 34mDelta
Wed 12/108:10 amMIA - OAK
2 stops10h 54mDelta
Deal found 11/4$262
This Southwest deal was found by Cheapflights users on 11/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:50 amOAK - MIA
1 stop9h 05mSouthwest
Wed 12/101:05 pmMIA - OAK
1 stop8h 35mSouthwest
Deal found 11/5$263
This Delta deal was found by Cheapflights users on 11/5. 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 12/104:50 pmOAK - MIA
1 stop10h 34mDelta
Tue 12/166:50 pmMIA - OAK
1 stop8h 18mDelta
Deal found 11/5$267
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amOAK - MIA
2 stops10h 25mSouthwest
Sat 12/66:05 amMIA - OAK
1 stop7h 50mSouthwest
Deal found 11/4$282
This Delta deal was found by Cheapflights users on 11/4. 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 12/95:55 amOAK - MIA
2 stops12h 55mDelta
Tue 12/1612:00 pmMIA - OAK
2 stops15h 08mDelta
Deal found 11/4$298
This Delta deal was found by Cheapflights users on 11/4. 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 12/245:53 amOAK - EYW
2 stops10h 50mDelta
Thu 12/2511:47 amEYW - OAK
2 stops14h 00mDelta
Deal found 11/4$1,207
This Delta deal was found by Cheapflights users on 11/4. 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 12/245:53 amOAK - EYW
2 stops10h 50mDelta
Mon 12/291:02 pmEYW - OAK
2 stops13h 56mDelta
Deal found 11/4$1,327
This Delta deal was found by Cheapflights users on 11/4. 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 12/185:55 amOAK - EYW
2 stops11h 11mDelta
Thu 12/2511:47 amEYW - OAK
2 stops14h 00mDelta
Deal found 11/4$1,328

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Florida Keys 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 November 6, 2025.
Use the filters below to find and compare flights from Oakland to Florida Keys that are best for you.

Fly from

Oakland

Fly to

Florida Keys

Route

Depart

Return

Price

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Tue 12/9

9:45 am-4:00 pm

1 stop27h 15m

Miami

Tue 12/16

6:34 pm-10:41 am

1 stop19h 07m

$251

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Wed 12/3

9:45 am-4:00 pm

1 stop27h 15m

Miami

Wed 12/10

6:34 pm-10:41 am

1 stop19h 07m

$251

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Tue 12/9

4:50 pm-11:21 am

2 stops15h 31m

Miami

Tue 12/16

6:50 pm-12:08 am

1 stop8h 18m

$262

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Mon 11/24

4:51 pm-6:25 am

1 stop10h 34m

Miami

Thu 12/4

3:50 pm-12:08 am

2 stops11h 18m

$262

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Sun 12/7

6:50 am-6:55 pm

1 stop9h 05m

Miami

Wed 12/10

1:05 pm-6:40 pm

1 stop8h 35m

$263

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Tue 1/20

4:54 pm-5:28 am

1 stop9h 34m

Miami

Fri 1/23

6:43 am-11:57 am

1 stop8h 14m

$268

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Mon 11/24

4:51 pm-6:25 am

1 stop10h 34m

Miami

Fri 12/5

7:15 pm-11:50 am

2 stops19h 35m

$310

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Tue 12/2

4:50 pm-6:24 am

1 stop10h 34m

Miami

Thu 12/4

6:50 pm-12:08 am

1 stop8h 18m

$312

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Tue 12/2

4:50 pm-6:24 am

1 stop10h 34m

Miami

Sat 12/6

8:10 am-4:10 pm

2 stops11h 00m

$317

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Thu 11/27

12:28 pm-6:25 am

1 stop14h 57m

Miami

Thu 12/4

6:50 pm-12:08 am

1 stop8h 18m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 31 results
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4

Best time to book a flight from Oakland to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys 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 Florida Keys

What is the cheapest month to book a flight from Oakland, California to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Oakland, California to Florida Keys (average of $227). Flying from Oakland, California to Florida Keys in June is currently the most expensive (average of $382). 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 Florida Keys

Get insights into the airlines that provide service to Florida Keys. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Florida Keys. Reviews last updated November 6, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Oakland to Florida Keys to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
9,003 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,115 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Florida Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Oakland to Florida Keys?

    For a flight from Oakland to Florida Keys, you will be flying from Oakland. Oakland (OAK) is just 7.0 mi from the center of the city.

  • How long is the flight from Oakland, California to Florida Keys?

    Alaska Airlines, Delta, and Southwest can get you from Oakland, California to Florida Keys in just under 9h 05m. Your travel time can differ by up to 18h 10m. Oakland, California and Florida Keys are separated by a distance of 2572 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Oakland to Florida Keys that include hotel bookings?

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

  • How can I find direct flights from Oakland to Florida Keys?

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

  • Can I find deals for business class flights from Oakland to Florida Keys?

    Yes. Cheapflights offers flight deals from Oakland to Florida Keys 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 Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Oakland, California to Florida Keys (average of $227). Flying from Oakland, California to Florida Keys in June is currently the most expensive (average of $382). 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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