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Kissimmee

$109+ Cheap flights from Oakland, CA (OAK) to Kissimmee, FL

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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MCO
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheapflights Tip: The best prices from Oakland to Kissimmee are usually found in September or October, booked 58 days in advance, depart on a Thursday or Monday and return on a Tuesday

Cheap flight deals from Oakland to Kissimmee

Cheapest flights from Oakland to Kissimmee
Explore the most affordable flight options available from Oakland to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This Delta deal was found by Cheapflights users on 12/19. 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.
Sun 12/285:53 amOAK - MCO
1 stop7h 12mDelta
Wed 1/74:47 pmMCO - OAK
1 stop9h 06mDelta
Deal found 12/19$682
This Southwest deal was found by Cheapflights users on 12/19. 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 12/3011:00 amOAK - MCO
1 stop7h 05mSouthwest
Tue 1/69:55 amMCO - OAK
1 stop10h 35mSouthwest
Deal found 12/19$722
This Alaska Airlines deal was found by Cheapflights users on 12/19. 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 12/319:49 amOAK - MCO
1 stop11h 39mAlaska Airlines
Tue 1/67:15 amMCO - OAK
1 stop9h 52mAlaska Airlines
Deal found 12/19$758
This Southwest deal was found by Cheapflights users on 12/20. 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.
Sat 12/279:55 amOAK - MCO
1 stop8h 05mSouthwest
Sat 1/32:00 pmMCO - OAK
1 stop10h 45mSouthwest
Deal found 12/20$778
This Southwest deal was found by Cheapflights users on 12/19. 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.
Sat 12/275:10 amOAK - MCO
1 stop7h 20mSouthwest
Sat 12/274:55 pmMCO - OAK
1 stop8h 55mSouthwest
Deal found 12/19$807
This Southwest deal was found by Cheapflights users on 12/19. 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.
Fri 12/265:50 pmOAK - MCO
1 stop9h 00mSouthwest
Wed 12/3111:15 amMCO - OAK
2 stops11h 35mSouthwest
Deal found 12/19$812
This Southwest deal was found by Cheapflights users on 12/18. 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 12/295:00 amOAK - MCO
1 stop9h 15mSouthwest
Sat 1/39:25 amMCO - OAK
1 stop9h 40mSouthwest
Deal found 12/18$827

Find flight deals from Oakland to Kissimmee

Keep the following information in mind while searching for Oakland to Kissimmee flight deals. Data was last updated December 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$256
(Alaska Airlines)

One-way from

$109
(Southwest)

Popular in

December

Cheapest in

September

Average price

$669
Provider with most accurate pricing for San Francisco-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Orlando (ORL) flights.
Search Deals
From Oakland to Kissimmee
Search Deals
One-way flight from Oakland to Kissimmee
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 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 Kissimmee 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 21, 2025.
Use the filters below to find and compare flights from Oakland to Kissimmee that are best for you.

Fly from

Oakland

Fly to

Kissimmee

Route

Depart

Return

Price

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sat 1/24

8:20 am-7:30 pm

1 stop8h 10m

Orlando

Sat 1/31

3:20 pm-8:25 pm

1 stop8h 05m

$257

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 2/24

9:40 am-10:05 pm

1 stop9h 25m

Orlando

Fri 2/27

6:40 am-2:10 pm

1 stop10h 30m

$257

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 1/20

10:40 am-10:00 pm

1 stop8h 20m

Orlando

Thu 1/22

11:05 am-5:30 pm

1 stop9h 25m

$257

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Mon 1/26

4:54 pm-8:49 am

2 stops12h 55m

Orlando

Fri 1/30

7:00 pm-11:53 pm

1 stop7h 53m

$262

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 2/24

6:15 am-11:59 pm

1 stop14h 44m

Orlando

Wed 2/25

7:00 am-4:37 pm

1 stop12h 37m

$270

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sat 1/31

11:08 am-7:35 am

1 stop17h 27m

Orlando

Tue 2/3

7:00 am-4:23 pm

1 stop12h 23m

$290

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Mon 1/12

12:38 pm-11:45 pm

1 stop8h 07m

Orlando

Wed 1/21

7:00 am-11:52 am

1 stop7h 52m

$298

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 1/13

8:30 pm-7:05 am

1 stop7h 35m

$109

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 2/24

4:59 pm-6:11 am

1 stop10h 12m

$129

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Fri 2/20

5:40 pm-5:50 am

1 stop9h 10m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 17 results
1
2

Best time to book a flight from Oakland to Kissimmee

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

How far ahead should I book a flight from Oakland, California to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from Oakland to Kissimmee. Price data was last updated on December 12, 2025.

Booking 58 days in advance of your planned departure date is, on average, the best time to get cheap flights from Oakland, California to Kissimmee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, May is the cheapest month in which you can book a flight from Oakland, California to Kissimmee (average of $128). Flying from Oakland, California to Kissimmee in December is currently the most expensive (average of $216). 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.

What is the cheapest time of day to fly from OAK to K1S?

Find hourly flight availability from Oakland to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 21, 2025.

When flying from Oakland, California to Kissimmee, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 40% versus a flight in the evening.

Reviews of airlines servicing Kissimmee

Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated December 21, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Oakland to Kissimmee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,494 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,494 reviews
Alaska Airlines
8.0
Very good
11,494 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
8.0
Very good
4,256 reviews
Alaska Airlines
8.0
Very good
11,494 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,017 reviews
Alaska Airlines
8.0
Very good
11,494 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Spirit Airlines
6.3
Okay
8,189 reviews
Alaska Airlines
8.0
Very good
11,494 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Kissimmee. 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 Kissimmee?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Oakland to Kissimmee. 4 airlines have flights from Oakland to Kissimmee on a regular basis. Booking flights from Oakland to Kissimmee should not be difficult; the airport handles an average of 0 outbound flights to Kissimmee per day.

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

    Departing from Oakland, California to Kissimmee will take you 8h 07m. The distance between Oakland, California and Kissimmee is about 2432 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $111. Users have also found prices from $112 and $128 on Spirit Airlines and Delta, respectively.

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

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

  • How can I find direct flights from Oakland to Kissimmee?

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

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

    Yes. Cheapflights offers flight deals from Oakland to Kissimmee 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 Kissimmee?

    Currently, May is the cheapest month in which you can book a flight from Oakland, California to Kissimmee (average of $128). Flying from Oakland, California to Kissimmee in December is currently the most expensive (average of $216). 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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Top 4 airlines flying from Oakland to Kissimmee

Discover the top 4 airlines that operate flights from Oakland to Kissimmee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$184Average$305FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$257Average$386FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$276Average$478FlexibilityNo cancel feeOn-time63%
DeltaCheapest$286Average$462FlexibilityNo cancel feeOn-timeN/A

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