HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kissimmee

$105+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MCO
Oct 18 — Oct 251
Sat 10/18
Sat 10/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Kissimmee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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

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 September 18, 2025.

Round-trip from

$209
(Southwest)

One-way from

$105
(Southwest)

Popular in

May

Cheapest in

September

Average price

$376
From Oakland to Kissimmee
Search Deals
One-way flight from Oakland to Kissimmee
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 18, 2025.

This Southwest deal was found by Cheapflights users on 9/16. 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 10/186:30 amOAK - MCO
1 stop8h 10mSouthwest
Sat 10/256:50 amMCO - OAK
1 stop9h 05mSouthwest
Deal found 9/16$209
This Southwest deal was found by Cheapflights users on 9/16. 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 10/248:45 pmOAK - MCO
1 stop7h 55mSouthwest
Tue 10/286:15 amMCO - OAK
2 stops8h 55mSouthwest
Deal found 9/16$214
This Southwest deal was found by Cheapflights users on 9/15. 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 10/269:00 pmOAK - MCO
1 stop7h 40mSouthwest
Wed 10/292:50 pmMCO - OAK
1 stop9h 00mSouthwest
Deal found 9/15$237
This Southwest deal was found by Cheapflights users on 9/16. 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 12/59:50 amOAK - MCO
1 stop9h 05mSouthwest
Fri 12/128:25 amMCO - OAK
1 stop9h 55mSouthwest
Deal found 9/16$247
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 10/258:05 pmOAK - MCO
1 stop8h 35mAlaska Airlines
Thu 10/304:29 pmMCO - OAK
1 stop10h 30mAlaska Airlines
Deal found 9/15$257
This Southwest deal was found by Cheapflights users on 9/15. 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 10/255:05 amOAK - MCO
1 stop6h 50mSouthwest
Wed 10/294:50 pmMCO - OAK
2 stops9h 10mSouthwest
Deal found 9/15$262
This Southwest deal was found by Cheapflights users on 9/17. 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 11/128:20 amOAK - MCO
1 stop7h 20mSouthwest
Fri 11/149:35 amMCO - OAK
2 stops10h 50mSouthwest
Deal found 9/17$272
This Delta deal was found by Cheapflights users on 9/15. 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 10/74:51 pmOAK - MCO
1 stop10h 04mDelta
Thu 10/166:39 pmMCO - OAK
1 stop8h 14mDelta
Deal found 9/15$284

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 September 18, 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

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

$231

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sat 12/6

10:05 am-9:20 pm

2 stops8h 15m

Orlando

Mon 12/15

4:10 pm-8:35 pm

1 stop7h 25m

$262

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sat 10/25

8:05 pm-7:40 am

1 stop8h 35m

Orlando

Tue 10/28

7:00 am-1:55 pm

1 stop9h 55m

$267

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Fri 12/5

12:35 pm-10:25 pm

1 stop6h 50m

Orlando

Fri 12/12

4:35 pm-9:20 pm

1 stop7h 45m

$277

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sat 10/18

6:30 am-5:40 pm

1 stop8h 10m

Orlando

Sat 10/25

12:45 pm-7:30 pm

1 stop9h 45m

$277

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sun 10/26

12:30 pm-11:59 pm

1 stop8h 29m

Orlando

Tue 10/28

7:00 am-11:50 am

1 stop7h 50m

$284

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Wed 10/15

8:35 pm-6:50 am

1 stop7h 15m

Orlando

Tue 10/21

6:15 am-12:10 pm

2 stops8h 55m

$298

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Fri 10/17

5:40 pm-6:10 am

1 stop9h 30m

Orlando

Sat 10/25

3:30 pm-9:25 pm

2 stops8h 55m

$342

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sat 12/6

7:15 pm-5:50 am

1 stop7h 35m

$105

OaklandOrlando

OAK - MCO

OAKMCO

Oakland

Sat 10/18

8:05 pm-6:50 am

1 stop7h 45m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

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 September 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 $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 September 18, 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.

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 September 18, 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
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
8.0
Very good
7,961 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
8,023 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

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 8h 15m. 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 $105. Users have also found prices from $119 and $129 on Alaska 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 $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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oakland to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to Orlando flights
Los Angeles to Miami flights
Los Angeles to Fort Lauderdale flights
San Francisco to Orlando flights
San Francisco to Miami flights
Los Angeles to Tampa flights
Ontario to Orlando flights
Ontario to Miami flights
Burbank to Fort Lauderdale flights
Las Vegas to Orlando flights
Santa Ana to Fort Lauderdale flights
San Diego to Orlando flights
San Diego to Miami flights
Santa Ana to Orlando flights
San Francisco to Tampa flights
San Francisco to Fort Lauderdale flights
Las Vegas to Fort Lauderdale flights
Ontario to Fort Lauderdale flights
Burbank to Orlando flights
Santa Ana to Miami flights
San Diego to Fort Lauderdale flights
Las Vegas to Miami flights
Burbank to Miami flights
Los Angeles to West Palm Beach flights
Sacramento to Orlando flights
San Jose to Orlando flights
Ontario to Tampa flights
San Diego to Tampa flights
San Jose to Miami flights
Sacramento to Miami flights
Santa Ana to Tampa flights
San Francisco to West Palm Beach flights
Las Vegas to Tampa flights
Oakland to Orlando flights
Burbank to Tampa flights
San Diego to Fort Myers flights
Sacramento to Fort Lauderdale flights
Ontario to West Palm Beach flights
Los Angeles to Fort Myers flights
Ontario to Jacksonville flights
San Francisco to Fort Myers flights
Oakland to Miami flights
Los Angeles to Jacksonville flights
Los Angeles to Pensacola flights
San Francisco to Jacksonville flights
Fresno to Orlando flights
Sacramento to Tampa flights
San Jose to Fort Lauderdale flights
San Diego to Jacksonville flights
Los Angeles to Sarasota flights

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 September 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$162Average$300FlexibilityNo cancel feeOn-time65%
DeltaCheapest$261Average$466FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$267Average$423FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$286Average$477FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$389Average$477FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.