$103 Cheap Flights from Oakland (OAK) to Fort Myers (RSW)

View $103 flight on Sat, Jul 5, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Oakland to Fort Myers (OAK-RSW)

Prices were available within the past 7 days and start at $103 for one-way flights and $263 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Thu, May 29 - Tue, Jun 3
OAK
Oakland
RSW
Fort Myers
$263 Roundtrip, just found
$263
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Oakland to Fort Myers, returning Tue, Jun 3, priced at $263 just found
Southwest Airlines
Wed, Nov 12 - Sun, Nov 16
OAK
Oakland
RSW
Fort Myers
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Oakland to Fort Myers, returning Sun, Nov 16, priced at $265 found 1 day ago
Delta
Tue, Jun 17 - Tue, Jun 24
OAK
Oakland
RSW
Fort Myers
$267 Roundtrip, found 6 hours ago
$267
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Jun 17 from Oakland to Fort Myers, returning Tue, Jun 24, priced at $267 found 6 hours ago
Southwest Airlines
Sun, Jun 1 - Wed, Jun 4
OAK
Oakland
RSW
Fort Myers
$277 Roundtrip, found 15 hours ago
$277
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sun, Jun 1 from Oakland to Fort Myers, returning Wed, Jun 4, priced at $277 found 15 hours ago
Spirit Airlines
Sun, Jun 1 - Wed, Jun 4
OAK
Oakland
RSW
Fort Myers
$284 Roundtrip, found 15 hours ago
$284
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Sun, Jun 1 from Oakland to Fort Myers, returning Wed, Jun 4, priced at $284 found 15 hours ago
Delta
Tue, Jun 17 - Sat, Jul 5
OAK
Oakland
RSW
Fort Myers
$292 Roundtrip, found 6 hours ago
$292
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Jun 17 from Oakland to Fort Myers, returning Sat, Jul 5, priced at $292 found 6 hours ago
Southwest Airlines
Wed, May 7 - Wed, May 14
OAK
Oakland
RSW
Fort Myers
$293 Roundtrip, found 9 hours ago
$293
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, May 7 from Oakland to Fort Myers, returning Wed, May 14, priced at $293 found 9 hours ago
Spirit Airlines
Thu, May 29 - Sun, Jun 1
OAK
Oakland
RSW
Fort Myers
$295 Roundtrip, found 4 days ago
$295
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, May 29 from Oakland to Fort Myers, returning Sun, Jun 1, priced at $295 found 4 days ago
Sun Country Airlines
Sun, Jun 1 - Wed, Jun 4
OAK
Oakland
RSW
Fort Myers
$308 Roundtrip, found 15 hours ago
$308
Roundtrip
found 15 hours ago
Select Sun Country Airlines flight, departing Sun, Jun 1 from Oakland to Fort Myers, returning Wed, Jun 4, priced at $308 found 15 hours ago
Alaska Airlines
Tue, Jun 3 - Tue, Jun 10
OAK
Oakland
RSW
Fort Myers
$361 Roundtrip, found 1 day ago
$361
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Jun 3 from Oakland to Fort Myers, returning Tue, Jun 10, priced at $361 found 1 day ago
Flights from Oakland (OAK) to Fort Myers (RSW)
Origin airport
Oakland Intl.
Destination airport
Southwest Florida Intl.
Airlines serving
Alaska Airlines, Delta, Southwest Airlines, Spirit Airlines
Roundtrip price
$263
Distance
2468 mi

Oakland to Fort Myers Flights

The cheapest times to fly from Oakland to Fort Myers

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Oakland to Fort Myers are during the month of May. You can find some of the cheapest flights from Oakland to Fort Myers with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Oakland to Fort Myers

Sunday is one of the best days to book for cheap flights from Oakland to Fort Myers: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Oakland to Fort Myers

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Oakland to Fort Myers in 2025. You can also book with separate airlines for your outbound and return journeys, from $103 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Oakland to Fort Myers flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Oakland to Fort Myers airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from Oakland Intl. Airport (OAK) to Southwest Florida Intl. Airport (RSW) cost?
Discover the latest flight deals from OAK to RSW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from OAK to RSW?
The cheapest flights from OAK to RSW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from OAK to RSW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from OAK to RSW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Oakland Intl. Airport (OAK) to Southwest Florida Intl. Airport (RSW)?
You’ll have to hop on a flight with a layover if you’re traveling from Oakland Intl. Airport (OAK) to Southwest Florida Intl. Airport (RSW). Direct flights don’t operate daily on this route. However, simply filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from OAK to RSW?
You’ll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Oakland Intl. Airport (OAK) to Southwest Florida Intl. Airport (RSW)?
Opt for a flight from Oakland Intl. Airport (OAK) to Southwest Florida Intl. Airport (RSW) that leaves before 3 PM to reduce the risk of cancellations. Departures later than this are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
Is it cheaper to buy a plane ticket from Oakland Intl. Airport (OAK) to Southwest Florida Intl. Airport (RSW) last-minute?
Booking your ticket from OAK to RSW right before your trip is typically more expensive. However, if there’s some wiggle room with your departure times and dates, you could grab a cheap last-minute fare.
Is it cheaper to book an OAK to RSW flight and hotel package?
You’ll generally save money by booking an OAK to RSW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it’s simple to manage everything in one place. After selecting your ideal accommodations and flights, consider adding extras such as tours, car rentals and activities.
Can I cancel or change the date of my flight from Oakland Intl. Airport (OAK) to Southwest Florida Intl. Airport (RSW)?
Usually, it’s possible to cancel or reschedule your OAK to RSW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline’s policies in your itinerary to see what changes are possible and if any costs are involved. You’ll also find more details on our Customer Service portal.

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*Available to One Key members.