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Florida Keys

$129+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — EYW
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap 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 December 23, 2025.

This Delta deal was found by Cheapflights users on 12/22. 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 12/3112:34 pmOAK - MIA
2 stops19h 00mDelta
Tue 1/136:45 amMIA - OAK
1 stop8h 12mDelta
Deal found 12/22$486
This Southwest deal was found by Cheapflights users on 12/21. 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 12/298:15 amOAK - MIA
1 stop12h 40mSouthwest
Thu 1/19:30 amMIA - OAK
1 stop14h 05mSouthwest
Deal found 12/21$492
This Delta deal was found by Cheapflights users on 12/22. 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 12/3112:34 pmOAK - MIA
2 stops19h 00mDelta
Mon 1/126:45 amMIA - OAK
1 stop8h 12mDelta
Deal found 12/22$497
This Delta deal was found by Cheapflights users on 12/22. 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 12/3112:34 pmOAK - MIA
2 stops19h 00mDelta
Wed 1/146:45 amMIA - OAK
1 stop8h 12mDelta
Deal found 12/22$526
This Delta deal was found by Cheapflights users on 12/22. 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 12/3112:34 pmOAK - MIA
2 stops19h 00mDelta
Thu 1/88:15 amMIA - OAK
2 stops10h 59mDelta
Deal found 12/22$531
This Southwest deal was found by Cheapflights users on 12/22. 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.
Tue 12/235:00 amOAK - MIA
1 stop10h 30mSouthwest
Mon 12/296:00 amMIA - OAK
2 stops12h 10mSouthwest
Deal found 12/22$534
This Alaska Airlines deal was found by Cheapflights users on 12/22. 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 12/313:01 pmOAK - MIA
1 stop12h 04mAlaska Airlines
Wed 1/146:34 pmMIA - OAK
1 stop29h 06mAlaska Airlines
Deal found 12/22$569
This Southwest deal was found by Cheapflights users on 12/21. 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.
Thu 12/255:45 amOAK - MIA
1 stop7h 15mSouthwest
Thu 1/112:00 pmMIA - OAK
1 stop11h 35mSouthwest
Deal found 12/21$580

Find 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 December 23, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$257
(Delta)

One-way from

$129
(Delta)

Popular in

December

Cheapest in

January

Average price

$503
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.
Search Deals
From Oakland to Florida Keys
Search Deals
One-way flight from Oakland to Florida Keys
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 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 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 December 23, 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

Wed 1/21

4:54 pm-5:28 am

1 stop9h 34m

Miami

Tue 1/27

6:43 am-11:52 am

1 stop8h 09m

$257

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Mon 1/26

4:54 pm-5:28 am

1 stop9h 34m

Miami

Wed 1/28

6:43 am-11:52 am

1 stop8h 09m

$268

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Sat 3/7

6:15 am-2:44 pm

2 stops29h 29m

Miami

Mon 3/9

4:44 pm-9:24 am

1 stop19h 40m

$287

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Tue 1/6

4:54 pm-5:30 am

1 stop9h 36m

Miami

Tue 1/13

6:45 am-11:57 am

1 stop8h 12m

$297

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Mon 2/16

6:15 am-4:59 pm

1 stop31h 44m

Miami

Wed 2/18

5:59 pm-10:49 pm

1 stop31h 50m

$304

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Mon 2/16

6:45 am-7:05 pm

2 stops9h 20m

Miami

Sat 2/21

7:45 am-5:40 pm

2 stops12h 55m

$383

OaklandMiami

OAK - MIA

OAKMIA

Oakland

Mon 3/23

7:35 pm-2:25 pm

2 stops15h 50m

Miami

Sat 3/28

5:15 pm-12:10 am

2 stops9h 55m

$383

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Sun 1/18

5:55 am-11:25 am

2 stops26h 30m

Key West

Sat 1/24

6:06 pm-4:14 pm

2 stops49h 08m

$900

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Wed 1/21

5:55 am-7:40 pm

2 stops10h 45m

Key West

Wed 1/28

7:10 am-4:14 pm

2 stops12h 04m

$909

OaklandKey West

OAK - EYW

OAKEYW

Oakland

Sat 1/17

12:38 pm-7:40 pm

2 stops28h 02m

Key West

Sat 1/24

6:06 pm-4:14 pm

2 stops49h 08m

$926

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 26 results
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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 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.

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 December 23, 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
4,256 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,015 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,109 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Spirit Airlines
6.3
Okay
8,194 reviews
Southwest
8.0
Very good
4,256 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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?

    Delta and Alaska Airlines can get you from Oakland, California to Florida Keys in just under 9h 34m. Your travel time can differ by up to 19h 55m. 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.

  • What are the cheapest airlines to fly from Oakland, California to Florida Keys one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $125. Delta flights start at $128 while deals on United Airlines start at $143 one-way.

  • 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 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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