$90+ Cheap flights from San Jose, CA (SJC) 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MCO
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from San Jose 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 San Jose to Kissimmee
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Cheapest flights from San Jose to KissimmeeExplore the most affordable flight options available from San Jose to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
Explore the most affordable flight options available from San Jose to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
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.
Wed 2/257:30 pm
SJC
- MCO
1 stop7h 20m
Southwest
Fri 2/275:50 pm
MCO
- SJC
1 stop8h 05m
Southwest
Deal found 2/3![Southwest logo]()
$317
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.
Tue 3/32:48 pm
SJC
- MCO
2 stops13h 52m
Alaska Airlines
Tue 3/107:44 am
MCO
- SJC
1 stop9h 29m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$320
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 2/286:35 am
SJC
- MCO
2 stops10h 25m
Southwest
Sat 3/75:50 pm
MCO
- SJC
1 stop8h 00m
Southwest
Deal found 2/1![Southwest logo]()
$322
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:15 pm
SJC
- MCO
1 stop6h 50m
American Airlines
Tue 3/316:40 am
MCO
- SJC
1 stop9h 49m
American Airlines
Deal found 2/2![American Airlines logo]()
$323
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.
Tue 4/76:45 am
SJC
- MCO
1 stop8h 10m
Southwest
Mon 4/136:15 pm
MCO
- SJC
1 stop8h 15m
Southwest
Deal found 2/1![Southwest logo]()
$324
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:32 pm
SJC
- MCO
1 stop29h 15m
Multiple Airlines
Fri 4/177:00 am
MCO
- SJC
2 stops14h 02m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 1/31. 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 2/216:35 am
SJC
- MCO
2 stops10h 25m
Southwest
Sat 2/288:45 am
MCO
- SJC
2 stops10h 00m
Southwest
Deal found 1/31![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 1/31. 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 2/257:50 am
SJC
- MCO
2 stops9h 15m
Southwest
Mon 3/235:00 pm
MCO
- SJC
1 stop8h 40m
Southwest
Deal found 1/31![Southwest logo]()
$329
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
SJC
- MCO
1 stop9h 22m
American Airlines
Sat 5/28:00 am
MCO
- SJC
1 stop8h 12m
American Airlines
Deal found 2/1![American Airlines logo]()
$332
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 3/106:10 am
SJC
- MCO
2 stops9h 45m
Southwest
Tue 3/313:55 pm
MCO
- SJC
2 stops10h 50m
Southwest
Deal found 2/2![Southwest logo]()
$333
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.
Tue 2/242:50 pm
SJC
- MCO
1 stop11h 50m
Alaska Airlines
Sat 2/287:44 am
MCO
- SJC
1 stop9h 32m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$334
Best flights from San Jose to KissimmeeDiscover carefully curated flight deals from San Jose to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from San Jose to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 pm
SJC
- MCO
1 stop7h 49m
Delta
Fri 4/176:15 am
MCO
- SJC
1 stop9h 05m
Delta
Deal found 2/2![Delta logo]()
$317
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.
Wed 4/226:15 am
SJC
- MCO
1 stop7h 50m
Southwest
Mon 4/275:05 pm
MCO
- SJC
2 stops9h 50m
Southwest
Deal found 2/1![Southwest logo]()
$322
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:45 am
SJC
- MCO
2 stops10h 14m
United Airlines
Fri 4/244:48 pm
MCO
- SJC
1 stop8h 48m
United Airlines
Deal found 2/1![United Airlines logo]()
$322
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:15 pm
SJC
- MCO
1 stop6h 50m
American Airlines
Tue 3/316:40 am
MCO
- SJC
1 stop9h 49m
American Airlines
Deal found 2/2![American Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 1/31. 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 2/211:55 pm
SJC
- MCO
1 stop6h 40m
Delta
Sat 2/286:00 am
MCO
- SJC
1 stop9h 52m
Delta
Deal found 1/31![Delta logo]()
$317
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.
Tue 4/76:45 am
SJC
- MCO
2 stops9h 05m
Southwest
Mon 4/135:30 pm
MCO
- SJC
2 stops8h 55m
Southwest
Deal found 2/1![Southwest logo]()
$327
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.
Wed 2/251:57 pm
SJC
- MCO
1 stop7h 06m
Delta
Wed 3/46:00 am
MCO
- SJC
1 stop9h 52m
Delta
Deal found 2/1![Delta logo]()
$317
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 3/107:30 pm
SJC
- MCO
1 stop6h 55m
Southwest
Tue 3/317:00 am
MCO
- SJC
2 stops9h 45m
Southwest
Deal found 2/2![Southwest logo]()
$328
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.
Sat 3/146:25 pm
SJC
- MCO
1 stop10h 00m
Delta
Sat 3/216:05 am
MCO
- SJC
1 stop9h 47m
Delta
Deal found 2/1![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 1/31. 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 2/257:50 am
SJC
- MCO
2 stops9h 15m
Southwest
Mon 3/235:00 pm
MCO
- SJC
1 stop8h 40m
Southwest
Deal found 1/31![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 1/31. 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 3/316:15 pm
SJC
- MCO
1 stop10h 25m
Delta
Fri 4/37:10 am
MCO
- SJC
1 stop8h 21m
Delta
Deal found 1/31![Delta logo]()
$317
Last-minute flights from San Jose to KissimmeeDiscover last-minute flight deals from San Jose to Kissimmee. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Kissimmee. Data last updated February 3, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 1/31. 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 2/216:35 am
SJC
- MCO
2 stops10h 25m
Southwest
Sat 2/288:45 am
MCO
- SJC
2 stops10h 00m
Southwest
Deal found 1/31![Southwest logo]()
$327
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.
Tue 2/242:50 pm
SJC
- MCO
1 stop11h 50m
Alaska Airlines
Sat 2/287:44 am
MCO
- SJC
1 stop9h 32m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$334
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.
Wed 2/257:30 pm
SJC
- MCO
1 stop7h 20m
Southwest
Fri 2/275:50 pm
MCO
- SJC
1 stop8h 05m
Southwest
Deal found 2/3![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 1/31. 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 2/257:50 am
SJC
- MCO
2 stops9h 15m
Southwest
Mon 3/235:00 pm
MCO
- SJC
1 stop8h 40m
Southwest
Deal found 1/31![Southwest logo]()
$329
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 2/286:35 am
SJC
- MCO
2 stops10h 25m
Southwest
Sat 3/75:50 pm
MCO
- SJC
1 stop8h 00m
Southwest
Deal found 2/1![Southwest logo]()
$322
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.
Tue 3/32:48 pm
SJC
- MCO
2 stops13h 52m
Alaska Airlines
Tue 3/107:44 am
MCO
- SJC
1 stop9h 29m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$320
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:15 pm
SJC
- MCO
1 stop6h 50m
American Airlines
Tue 3/316:40 am
MCO
- SJC
1 stop9h 49m
American Airlines
Deal found 2/2![American Airlines logo]()
$323
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 3/106:10 am
SJC
- MCO
2 stops9h 45m
Southwest
Tue 3/313:55 pm
MCO
- SJC
2 stops10h 50m
Southwest
Deal found 2/2![Southwest logo]()
$333
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:42 pm
SJC
- MCO
1 stop8h 44m
Frontier
Sat 3/2110:45 pm
MCO
- SJC
2 stops37h 40m
Frontier
Deal found 2/1![Frontier logo]()
$339
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.
Mon 3/232:10 pm
SJC
- MCO
1 stop7h 35m
Southwest
Fri 3/276:35 pm
MCO
- SJC
1 stop7h 45m
Southwest
Deal found 2/1![Southwest logo]()
$340
One-way flights from San Jose to KissimmeeSearch for one-way flight options from San Jose to Kissimmee. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from San Jose to Kissimmee. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:35 am
SJC
- MCO
1 stop17h 55m
Frontier
Deal found 2/1![Frontier logo]()
$90
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:02 pm
SJC
- MCO
1 stop8h 28m
Frontier
Deal found 2/1![Frontier logo]()
$109
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:20 pm
SJC
- MCO
1 stop8h 06m
Frontier
Deal found 2/2![Frontier logo]()
$119
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:20 pm
SJC
- MCO
3 stops14h 29m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$134
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/47:32 pm
SJC
- MCO
1 stop9h 01m
Frontier
Deal found 2/3![Frontier logo]()
$145
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/198:20 pm
SJC
- MCO
1 stop8h 13m
Frontier
Deal found 2/2![Frontier logo]()
$155
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2411:02 am
SJC
- MCO
1 stop7h 29m
American Airlines
Deal found 2/2![American Airlines logo]()
$159
This Southwest deal was found by Cheapflights users on 1/31. 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 3/248:40 am
SJC
- MCO
2 stops9h 20m
Southwest
Deal found 1/31![Southwest logo]()
$164
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.
Thu 5/219:45 pm
SJC
- MCO
1 stop8h 00m
Southwest
Deal found 2/1![Southwest logo]()
$166
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:49 pm
SJC
- MCO
2 stops38h 25m
Frontier
Deal found 2/3![Frontier logo]()
$176
Find flight deals from San Jose to Kissimmee
Keep the following information in mind while searching for San Jose to Kissimmee flight deals. Data was last updated February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (United Airlines) |
One-way from | $90 (CheapOair) |
Popular in | December |
Cheapest in | January |
Average price | $478 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose 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 3, 2026.
Use the filters below to find and compare flights from San Jose to Kissimmee that are best for you.
Fly from
San Jose
Fly to
Kissimmee
Route
Depart
Return
Price
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Mon 4/13
10:55 pm-9:44 am
1 stop7h 49m
Orlando
Fri 4/17
6:15 am-12:20 pm
1 stop9h 05m
$317
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Sat 2/21
1:55 pm-11:35 pm
1 stop6h 40m
Orlando
Sat 2/28
6:00 am-12:52 pm
1 stop9h 52m
$317
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Wed 2/25
1:57 pm-12:03 am
1 stop7h 06m
Orlando
Wed 3/4
6:00 am-12:52 pm
1 stop9h 52m
$317
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Sat 3/14
6:25 pm-7:25 am
1 stop10h 00m
Orlando
Sat 3/21
6:05 am-12:52 pm
1 stop9h 47m
$317
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Tue 3/31
6:15 pm-7:40 am
1 stop10h 25m
Orlando
Fri 4/3
7:10 am-12:31 pm
1 stop8h 21m
$317
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Wed 4/22
6:15 am-5:05 pm
1 stop7h 50m
Orlando
Mon 4/27
5:05 pm-11:55 pm
2 stops9h 50m
$322
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Sat 4/18
8:45 am-9:59 pm
2 stops10h 14m
Orlando
Fri 4/24
4:48 pm-10:36 pm
1 stop8h 48m
$322
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Tue 3/10
7:15 pm-5:05 am
1 stop6h 50m
Orlando
Tue 3/31
6:40 am-1:29 pm
1 stop9h 49m
$323
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Tue 4/7
6:45 am-6:50 pm
2 stops9h 05m
Orlando
Mon 4/13
5:30 pm-11:25 pm
2 stops8h 55m
$327
San JoseOrlando
SJC - MCO
SJCMCO
San Jose
Tue 3/10
7:30 pm-5:25 am
1 stop6h 55m
Orlando
Tue 3/31
7:00 am-1:45 pm
2 stops9h 45m
$328
Showing 1-10 of 21 results
Best time to book a flight from San Jose to Kissimmee
Have a flexible travel schedule? Discover the best time to fly to Kissimmee from San Jose with our price prediction graph.
SJC-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 San Jose to Kissimmee
SJC-K1S
SJC-MCO
How far ahead should I book a flight from San Jose, California to Kissimmee?
Use this chart to determine the optimal time to book a round-trip flight from San Jose to Kissimmee. Price data was last updated on January 30, 2026.
The best time to book flights from San Jose, California to Kissimmee is 48 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from San Jose, California to Kissimmee?
Currently, May is the cheapest month in which you can book a flight from San Jose, California to Kissimmee (average of $128). Flying from San Jose, 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 3, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from San Jose 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.
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from San Jose 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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Alternative routes for San Jose to Kissimmee
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from San Jose to Kissimmee
Discover the top 7 airlines that operate flights from San Jose 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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$117 | Average$276 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$167 | Average$272 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$434 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$267 | Average$459 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$271 | Average$454 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$276 | Average$432 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$285 | Average$444 | FlexibilityNo cancel fee | On-timeN/A |