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Kissimmee

$128+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MCO
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheapflights Tip: The best prices from Oakland to Kissimmee are usually found in September or June, booked 58 days in advance, depart on a Thursday or Monday and return on a Tuesday

Find 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 November 3, 2025.

This Delta deal was found by Cheapflights users on 11/3. 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 - MCO
1 stop10h 10mDelta
Wed 12/105:01 pmMCO - OAK
1 stop10h 07mDelta
Deal found 11/3$257
This Delta deal was found by Cheapflights users on 11/3. 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 12/75:55 amOAK - MCO
2 stops12h 33mDelta
Wed 12/105:01 pmMCO - OAK
1 stop10h 07mDelta
Deal found 11/3$262
This Delta deal was found by Cheapflights users on 11/3. 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 12/35:55 amOAK - MCO
2 stops12h 17mDelta
Wed 12/108:15 amMCO - OAK
2 stops10h 49mDelta
Deal found 11/3$267
This Southwest deal was found by Cheapflights users on 11/2. 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 12/74:00 pmOAK - MCO
1 stop10h 25mSouthwest
Tue 12/166:55 amMCO - OAK
2 stops11h 25mSouthwest
Deal found 11/2$268
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:21 amOAK - MCO
1 stop9h 37mAlaska Airlines
Wed 12/177:00 amMCO - OAK
1 stop9h 32mAlaska Airlines
Deal found 11/2$276
This Delta deal was found by Cheapflights users on 11/3. 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.
Sat 12/612:30 pmOAK - MCO
1 stop8h 40mDelta
Tue 12/97:10 amMCO - OAK
1 stop7h 40mDelta
Deal found 11/3$277
This Delta deal was found by Cheapflights users on 11/3. 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.
Sat 12/65:55 amOAK - MCO
2 stops12h 33mDelta
Fri 12/126:35 pmMCO - OAK
1 stop8h 33mDelta
Deal found 11/3$282
This Delta deal was found by Cheapflights users on 11/3. 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.
Sat 12/65:55 amOAK - MCO
2 stops9h 29mDelta
Wed 12/103:00 pmMCO - OAK
2 stops12h 08mDelta
Deal found 11/3$287
This Delta deal was found by Cheapflights users on 11/3. 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 12/144:50 pmOAK - MCO
1 stop10h 10mDelta
Tue 12/165:01 pmMCO - OAK
1 stop10h 07mDelta
Deal found 11/3$288
This Delta deal was found by Cheapflights users on 11/3. 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 12/35:55 amOAK - MCO
2 stops12h 17mDelta
Thu 12/117:10 amMCO - OAK
1 stop7h 40mDelta
Deal found 11/3$293
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 12/1111:21 amOAK - MCO
1 stop9h 37mAlaska Airlines
Tue 12/167:00 amMCO - OAK
1 stop9h 32mAlaska Airlines
Deal found 11/3$296
This Delta deal was found by Cheapflights users on 11/3. 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.
Fri 12/54:50 pmOAK - MCO
1 stop10h 10mDelta
Tue 12/95:01 pmMCO - OAK
1 stop10h 07mDelta
Deal found 11/3$297

Cheap flight deals from Oakland to Kissimmee

Keep the following information in mind while searching for Oakland to Kissimmee flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$256
(Alaska Airlines)

One-way from

$128
(Alaska Airlines)

Popular in

May

Cheapest in

September

Average price

$458
Provider with most accurate pricing for San Francisco-Orlando (ORL) flight deals.
Search Deals
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. 2% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 3, 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

Mon 12/8

4:50 pm-6:00 am

1 stop10h 10m

Orlando

Wed 12/10

5:01 pm-12:08 am

1 stop10h 07m

$257

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 12/9

4:50 pm-6:00 am

1 stop10h 10m

Orlando

Wed 12/17

7:10 am-11:50 am

1 stop7h 40m

$257

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Mon 12/15

5:55 am-5:23 pm

1 stop8h 28m

Orlando

Tue 12/16

6:35 pm-12:08 am

1 stop8h 33m

$257

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 3/3

5:05 pm-5:46 am

1 stop9h 41m

Orlando

Wed 3/4

7:00 pm-11:53 pm

1 stop7h 53m

$257

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sun 12/7

4:00 pm-5:25 am

1 stop10h 25m

Orlando

Tue 12/16

6:55 am-3:20 pm

2 stops11h 25m

$268

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 3/3

6:35 pm-6:17 am

1 stop8h 42m

Orlando

Wed 3/4

10:00 am-5:43 pm

1 stop10h 43m

$271

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sat 12/6

4:50 pm-6:00 am

1 stop10h 10m

Orlando

Wed 12/10

6:35 pm-12:08 am

1 stop8h 33m

$277

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Thu 12/4

9:55 am-9:55 pm

1 stop9h 00m

Orlando

Tue 12/9

9:20 am-5:15 pm

1 stop10h 55m

$297

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Mon 1/12

5:17 pm-7:35 am

1 stop11h 18m

Orlando

Tue 1/20

7:00 am-4:23 pm

1 stop12h 23m

$297

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Mon 3/9

6:35 pm-6:17 am

1 stop8h 42m

Orlando

Mon 3/16

10:00 am-5:43 pm

1 stop10h 43m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 19 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 October 31, 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 June is currently the most expensive (average of $204). 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 November 3, 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 November 3, 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
11,236 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
11,236 reviews
Alaska Airlines
8.0
Very good
11,236 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,238 reviews
Alaska Airlines
8.0
Very good
11,236 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
7.9
Good
8,001 reviews
Alaska Airlines
8.0
Very good
11,236 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Spirit Airlines
6.3
Okay
8,115 reviews
Alaska Airlines
8.0
Very good
11,236 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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. 5 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 10h 10m. 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 Alaska Airlines. According to our data, you can fly for as low as $128. Users have also found prices from $169 and $189 on Southwest 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 June is currently the most expensive (average of $204). 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 5 airlines flying from Oakland to Kissimmee

Discover the top 5 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$209Average$312FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$237Average$423FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$276Average$480FlexibilityNo cancel feeOn-time63%
DeltaCheapest$286Average$462FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$389Average$523FlexibilityNo cancel feeOn-time69%

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