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Kissimmee

$78+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MCO
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Oakland to Kissimmee are usually found in May or January, booked 73 days in advance, depart on a Thursday or Monday and return on a Tuesday

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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$170
(CheapOair)

One-way from

$78
(Orbitz)

Popular in

December

Cheapest in

May

Average price

$356
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.
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From Oakland to Kissimmee
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One-way flight from Oakland to Kissimmee
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Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 May 1, 2025.

This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/289:09 pmOAK - MCO
2 stops13h 58mSpirit Airlines
Sat 5/316:17 amMCO - OAK
2 stops16h 57mSpirit Airlines
Deal found 4/29$170
This Delta deal was found by Cheapflights users on 4/30. 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.
Mon 6/306:00 amOAK - MCO
1 stop8h 59mDelta
Thu 7/107:15 pmMCO - OAK
1 stop7h 40mDelta
Deal found 4/30$257
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/122:07 pmOAK - MCO
3 stops46h 21mMultiple Airlines
Fri 5/163:11 pmMCO - OAK
3 stops24h 56mMultiple Airlines
Deal found 4/30$273
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 5/137:00 amOAK - MCO
1 stop8h 59mAlaska Airlines
Tue 5/204:39 pmMCO - OAK
1 stop10h 07mAlaska Airlines
Deal found 4/29$307
This Southwest deal was found by Cheapflights users on 4/29. 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 8/66:25 amOAK - MCO
1 stop7h 50mSouthwest
Mon 8/116:40 amMCO - OAK
2 stops10h 25mSouthwest
Deal found 4/29$352
This Sun Country Air deal was found by Cheapflights users on 4/29. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/241:49 pmOAK - MCO
1 stop18h 42mSun Country Air
Sun 7/277:15 pmMCO - OAK
1 stop24h 36mSun Country Air
Deal found 4/29$375

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 May 1, 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

Wed 5/28

9:09 pm-2:07 pm

2 stops13h 58m

Orlando

Sat 5/31

6:17 am-8:14 pm

2 stops16h 57m

$170

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Mon 6/30

6:00 am-5:59 pm

1 stop8h 59m

Orlando

Wed 7/16

11:50 am-4:14 pm

1 stop7h 24m

$257

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Mon 5/12

2:07 pm-3:28 pm

3 stops46h 21m

Orlando

Fri 5/16

3:11 pm-1:07 pm

3 stops24h 56m

$273

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 5/13

7:00 am-6:59 pm

1 stop8h 59m

Orlando

Tue 5/20

4:39 pm-11:46 pm

1 stop10h 07m

$307

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Wed 8/6

6:25 am-5:15 pm

1 stop7h 50m

Orlando

Mon 8/11

6:40 am-2:05 pm

2 stops10h 25m

$352

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Thu 7/24

1:49 pm-11:31 am

1 stop18h 42m

Orlando

Sun 7/27

7:15 pm-4:51 pm

1 stop24h 36m

$375

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 5/27

11:51 am-3:28 pm

2 stops24h 37m

$78

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Wed 5/28

12:48 pm-12:25 am

1 stop8h 37m

$128

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Tue 6/17

4:58 pm-5:39 am

1 stop9h 41m

$129

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Fri 6/6

5:45 am-8:27 pm

2 stops35h 42m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 13 results
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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 April 25, 2025.

Booking 72 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 $206). Flying from Oakland, California to Kissimmee in November is currently the most expensive (average of $289). 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 May 1, 2025.

When flying from Oakland, California to Kissimmee, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

Temperature in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 May 1, 2025.
To help decide which airline to fly from Oakland to Kissimmee, see what other customers have to say about Alaska Airlines, Southwest and Delta. 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
9,972 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Sun Country Air
6.9
Okay
346 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
7,963 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $78. Users have also found prices from $129 and $150 on Delta and Sun Country Air, 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 $206). Flying from Oakland, California to Kissimmee in November is currently the most expensive (average of $289). 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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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$162Average$321FlexibilityNo cancel feeOn-time65%
DeltaCheapest$261Average$468FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$275Average$515FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$356Average$500FlexibilityNo cancel feeOn-time63%

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