$119+ 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MCO
Mar 6 — Mar 131
1 adult, Economy
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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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Oakland to Kissimmee
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Best
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One-way
Cheapest flights from Oakland to KissimmeeExplore 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 February 4, 2026.
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 February 4, 2026.
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:31 pm
OAK
- MCO
1 stop11h 09m
Hawaiian Airlines
Tue 3/107:00 am
MCO
- OAK
1 stop12h 37m
Hawaiian Airlines
Deal found 2/2![Hawaiian Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 3/37:40 am
OAK
- MCO
1 stop8h 45m
Southwest
Tue 3/106:40 am
MCO
- OAK
1 stop9h 35m
Southwest
Deal found 2/2![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:55 pm
OAK
- MCO
1 stop7h 05m
Southwest
Tue 3/311:20 pm
MCO
- OAK
1 stop9h 35m
Southwest
Deal found 2/3![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:50 pm
OAK
- MCO
1 stop6h 35m
Southwest
Tue 3/177:05 am
MCO
- OAK
1 stop11h 00m
Southwest
Deal found 2/3![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 4/117:35 pm
OAK
- MCO
1 stop6h 55m
Southwest
Sat 4/188:15 am
MCO
- OAK
1 stop11h 40m
Southwest
Deal found 2/2![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 2/2. 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 3/15:25 am
OAK
- MCO
1 stop7h 50m
Southwest
Mon 3/95:15 pm
MCO
- OAK
1 stop8h 05m
Southwest
Deal found 2/2![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1810:45 am
OAK
- MCO
2 stops8h 20m
Southwest
Sat 4/258:00 am
MCO
- OAK
1 stop14h 00m
Southwest
Deal found 2/3![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 2/245:25 am
OAK
- MCO
2 stops8h 55m
Southwest
Sat 2/2811:55 am
MCO
- OAK
1 stop8h 45m
Southwest
Deal found 2/2![Southwest logo]()
$292
Best flights from Oakland to KissimmeeDiscover carefully curated flight deals from Oakland to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
Discover carefully curated flight deals from Oakland to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 3/33:30 pm
OAK
- MCO
2 stops11h 20m
Southwest
Tue 3/107:15 am
MCO
- OAK
1 stop8h 30m
Southwest
Deal found 2/2![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 2/1. 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 3/174:49 pm
OAK
- MCO
1 stop10h 04m
Delta
Mon 3/237:00 pm
MCO
- OAK
1 stop7h 46m
Delta
Deal found 2/1![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 4/117:35 pm
OAK
- MCO
1 stop6h 55m
Southwest
Sat 4/188:15 am
MCO
- OAK
1 stop11h 40m
Southwest
Deal found 2/2![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 2/1. 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 2/286:25 pm
OAK
- MCO
1 stop9h 35m
Southwest
Tue 3/107:05 am
MCO
- OAK
1 stop11h 00m
Southwest
Deal found 2/1![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 2/246:25 am
OAK
- MCO
1 stop8h 40m
Southwest
Sat 2/286:10 am
MCO
- OAK
1 stop8h 05m
Southwest
Deal found 2/2![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 5/95:00 am
OAK
- MCO
2 stops9h 55m
Southwest
Sun 5/107:30 pm
MCO
- OAK
1 stop8h 15m
Southwest
Deal found 2/2![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 2/2. 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.
Mon 4/139:30 pm
OAK
- MCO
1 stop6h 40m
Southwest
Fri 4/175:45 pm
MCO
- OAK
1 stop7h 50m
Southwest
Deal found 2/2![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/268:25 pm
OAK
- MCO
1 stop7h 35m
Southwest
Sat 2/284:40 pm
MCO
- OAK
1 stop8h 05m
Southwest
Deal found 2/3![Southwest logo]()
$337
Last-minute flights from Oakland to KissimmeeDiscover last-minute flight deals from Oakland to Kissimmee. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Kissimmee. Data last updated February 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:25 am
OAK
- MCO
2 stops8h 55m
Southwest
Sat 2/286:10 am
MCO
- OAK
1 stop8h 05m
Southwest
Deal found 2/3![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 2/3. 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 2/244:59 pm
OAK
- MCO
1 stop10h 12m
Delta
Tue 3/37:00 pm
MCO
- OAK
1 stop7h 51m
Delta
Deal found 2/3![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:50 pm
OAK
- MCO
1 stop6h 35m
Southwest
Tue 3/177:05 am
MCO
- OAK
1 stop11h 00m
Southwest
Deal found 2/3![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 2/2. 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 3/15:25 am
OAK
- MCO
1 stop7h 50m
Southwest
Mon 3/95:15 pm
MCO
- OAK
1 stop8h 05m
Southwest
Deal found 2/2![Southwest logo]()
$287
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:31 pm
OAK
- MCO
1 stop11h 09m
Hawaiian Airlines
Tue 3/107:00 am
MCO
- OAK
1 stop12h 37m
Hawaiian Airlines
Deal found 2/2![Hawaiian Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 2/2. 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.
Tue 3/37:40 am
OAK
- MCO
1 stop8h 45m
Southwest
Tue 3/106:40 am
MCO
- OAK
1 stop9h 35m
Southwest
Deal found 2/2![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 2/3. 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 3/312:40 pm
OAK
- MCO
1 stop8h 10m
Delta
Wed 3/254:46 pm
MCO
- OAK
1 stop10h 00m
Delta
Deal found 2/3![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:55 pm
OAK
- MCO
1 stop7h 05m
Southwest
Tue 3/311:20 pm
MCO
- OAK
1 stop9h 35m
Southwest
Deal found 2/3![Southwest logo]()
$257
One-way flights from Oakland to KissimmeeSearch for one-way flight options from Oakland to Kissimmee. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Oakland to Kissimmee. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Southwest deal was found by Cheapflights users on 2/2. 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.
Wed 3/117:35 pm
OAK
- MCO
1 stop6h 50m
Southwest
Deal found 2/2![Southwest logo]()
$119
This Delta deal was found by Cheapflights users on 2/3. 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 4/155:04 pm
OAK
- MCO
1 stop10h 04m
Delta
Deal found 2/3![Delta logo]()
$129
This Delta deal was found by Cheapflights users on 2/3. 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 3/115:55 am
OAK
- MCO
2 stops9h 20m
Delta
Deal found 2/3![Delta logo]()
$134
This CheapOair deal was found by Cheapflights users on 2/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:31 pm
OAK
- MCO
1 stop11h 09m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$149
This CheapOair deal was found by Cheapflights users on 2/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:59 pm
OAK
- MCO
1 stop18h 08m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$154
This Alaska Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 5/127:19 pm
OAK
- MCO
1 stop7h 36m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$159
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:00 am
OAK
- MCO
1 stop19h 55m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 2/2. 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.
Thu 2/268:25 pm
OAK
- MCO
1 stop7h 35m
Southwest
Deal found 2/2![Southwest logo]()
$169
This CheapOair deal was found by Cheapflights users on 2/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:15 am
OAK
- MCO
2 stops13h 42m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$174
This CheapOair deal was found by Cheapflights users on 2/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:40 pm
OAK
- MCO
2 stops12h 06m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$184
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:30 pm
OAK
- MCO
1 stop7h 25m
Southwest
Deal found 2/3![Southwest logo]()
$189
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 February 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $224 (Trip.com) |
One-way from | $119 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $522 |
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 February 4, 2026.
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
3:30 pm-5:50 am
2 stops11h 20m
Orlando
Tue 3/10
7:15 am-12:45 pm
1 stop8h 30m
$272
OaklandOrlando
OAK - MCO
OAKMCO
Oakland
Sat 4/11
7:35 pm-5:30 am
1 stop6h 55m
Orlando
Sat 4/18
8:15 am-4:55 pm
1 stop11h 40m
$282
OaklandOrlando
OAK - MCO
OAKMCO
Oakland
Sat 2/28
6:25 pm-7:00 am
1 stop9h 35m
Orlando
Tue 3/10
7:05 am-3:05 pm
1 stop11h 00m
$287
OaklandOrlando
OAK - MCO
OAKMCO
Oakland
Tue 2/24
6:25 am-6:05 pm
1 stop8h 40m
Orlando
Sat 2/28
6:10 am-11:15 am
1 stop8h 05m
$287
OaklandOrlando
OAK - MCO
OAKMCO
Oakland
Sat 5/9
5:00 am-5:55 pm
2 stops9h 55m
Orlando
Sun 5/10
7:30 pm-12:45 am
1 stop8h 15m
$312
OaklandOrlando
OAK - MCO
OAKMCO
Oakland
Mon 4/13
9:30 pm-7:10 am
1 stop6h 40m
Orlando
Fri 4/17
5:45 pm-10:35 pm
1 stop7h 50m
$317
OaklandOrlando
OAK - MCO
OAKMCO
Oakland
Tue 3/17
4:49 pm-5:53 am
1 stop10h 04m
Orlando
Mon 3/23
7:00 pm-11:46 pm
1 stop7h 46m
$337
OaklandOrlando
OAK - MCO
OAKMCO
Oakland
Thu 2/26
8:25 pm-7:00 am
1 stop7h 35m
Orlando
Sat 2/28
4:40 pm-9:45 pm
1 stop8h 05m
$337
OaklandOrlando
OAK - MCO
OAKMCO
Oakland
Wed 3/11
6:10 pm-6:15 am
1 stop9h 05m
$119
OaklandOrlando
OAK - MCO
OAKMCO
Oakland
Tue 3/10
6:15 am-7:09 pm
1 stop9h 54m
$119
Showing 1-10 of 17 results
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.
OAK-MCO
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
OAK-K1S
OAK-MCO
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 January 30, 2026.
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 $232). 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.
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 February 4, 2026.
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.
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
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.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Oakland to Kissimmee
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Complete your trip
Complete your trip to Kissimmee by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Oakland to Kissimmee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oakland and Kissimmee flights
Browse other Oakland and Kissimmee flight options. Last updated on February 4, 2026.
Other flights from Oakland
Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on February 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oakland to Kissimmee flights
Consider these flights traveling from Oakland to Kissimmee.
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 February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$222 | Average$288 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$237 | Average$386 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$276 | Average$458 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$288 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$389 | Average$549 | FlexibilityNo cancel fee | On-time69% |