Kissimmee

$92+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MCO
May 1 — May 81
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Cheap flight deals from San Jose to Kissimmee

Cheapest flights from San Jose to Kissimmee
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 April 1, 2026.

This Southwest deal was found by Cheapflights users on 4/1. 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 5/28:15 am
SJC
-
MCO
2 stops8h 30m
Southwest
Sat 5/97:20 am
MCO
-
SJC
2 stops10h 05m
Southwest
Deal found 4/1$297
This CheapOair deal was found by Cheapflights users on 3/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:36 pm
SJC
-
MCO
1 stop8h 57m
Frontier
Sat 4/184:29 pm
MCO
-
SJC
1 stop29h 58m
Frontier
Deal found 3/31$301
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 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
2 stops21h 13m
Multiple Airlines
Wed 4/228:24 pm
MCO
-
SJC
1 stop24h 48m
Multiple Airlines
Deal found 3/29$305
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 5/46:39 pm
SJC
-
MCO
2 stops30h 30m
Frontier
Thu 5/143:46 pm
MCO
-
SJC
1 stop23h 13m
Frontier
Deal found 3/28$307
This Orbitz deal was found by Cheapflights users on 4/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:09 pm
SJC
-
MCO
1 stop8h 59m
Multiple Airlines
Sat 5/233:46 pm
MCO
-
SJC
1 stop23h 13m
Multiple Airlines
Deal found 4/1$308
This Expedia deal was found by Cheapflights users on 3/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/302:12 pm
SJC
-
MCO
1 stop12h 28m
Multiple Airlines
Mon 6/16:14 pm
MCO
-
SJC
1 stop7h 45m
Multiple Airlines
Deal found 3/27$310
This Expedia deal was found by Cheapflights users on 3/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/215:35 pm
SJC
-
MCO
1 stop9h 17m
Multiple Airlines
Sun 4/268:24 pm
MCO
-
SJC
1 stop24h 20m
Multiple Airlines
Deal found 3/31$313
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Sun 5/38:22 pm
SJC
-
MCO
2 stops29h 08m
Frontier
Thu 5/73:46 pm
MCO
-
SJC
1 stop23h 13m
Frontier
Deal found 3/27$321
This CheapOair deal was found by Cheapflights users on 3/29. 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.
Sat 4/117:36 pm
SJC
-
MCO
1 stop8h 57m
Frontier
Thu 4/168:24 pm
MCO
-
SJC
1 stop24h 20m
Frontier
Deal found 3/29$322
This Expedia deal was found by Cheapflights users on 3/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:39 pm
SJC
-
MCO
1 stop7h 25m
Multiple Airlines
Fri 4/246:59 pm
MCO
-
SJC
1 stop20h 04m
Multiple Airlines
Deal found 3/30$325
This Alaska Airlines deal was found by Cheapflights users on 3/31. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:09 pm
SJC
-
MCO
1 stop8h 59m
Alaska Airlines
Wed 6/36:14 pm
MCO
-
SJC
1 stop7h 45m
Alaska Airlines
Deal found 3/31$326

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 April 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$301
(CheapOair)

One-way from

$92
(CheapOair)

Popular in

December

Cheapest in

January

Average price

$471
Provider with most accurate pricing for San Jose-Orlando (ORL) flight deals.
Provider most trusted by Cheapflights users for San Jose-Orlando (ORL) flights.
From San Jose to Kissimmee
One-way flight from San Jose to Kissimmee
Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Average for round-trip flights in April 2026

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 April 1, 2026.
Use the filters below to find and compare flights from San Jose to Kissimmee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Mon 6/1

5:09 pm-5:08 am

1 stop8h 59m

Orlando

Wed 6/3

6:14 pm-10:59 pm

1 stop7h 45m

$326
Quickest round-trip

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Tue 4/28

7:40 pm-5:30 am

1 stop6h 50m

Orlando

Tue 5/5

2:55 pm-8:30 pm

1 stop8h 35m

$371

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Sun 4/19

9:45 pm-8:45 am

1 stop8h 00m

Orlando

Wed 4/22

9:05 am-5:25 pm

2 stops11h 20m

$375

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Sat 4/25

8:15 am-7:45 pm

2 stops8h 30m

Orlando

Sat 5/2

9:05 am-3:45 pm

1 stop9h 40m

$376

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Sat 5/2

8:55 am-7:45 pm

2 stops7h 50m

Orlando

Sat 5/9

9:05 am-3:45 pm

1 stop9h 40m

$376

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Tue 5/12

6:40 am-6:30 pm

2 stops8h 50m

Orlando

Tue 5/19

9:05 am-5:25 pm

2 stops11h 20m

$381

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Tue 5/19

6:20 am-5:04 pm

1 stop7h 44m

Orlando

Tue 5/26

6:05 am-12:18 pm

1 stop9h 13m

$385

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Fri 9/11

7:15 am-7:44 pm

1 stop9h 29m

Orlando

Sat 9/19

5:25 pm-10:41 pm

1 stop8h 16m

$389

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Mon 4/20

12:20 pm-12:55 am

2 stops9h 35m

Orlando

Fri 4/24

5:05 pm-11:55 pm

2 stops9h 50m

$389

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Wed 5/20

10:40 am-10:30 pm

1 stop8h 50m

Orlando

Wed 5/27

5:05 pm-9:55 pm

1 stop7h 50m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 21 resultsSorted by cheapest first
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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.
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

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 March 13, 2026.

The best time to book flights from San Jose, California to Kissimmee is 70 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 $233). 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.

How much does it cost to fly round-trip from San Jose, California to Kissimmee?

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 April 1, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andDelta 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.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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.
  • What airport do you fly from for flights from San Jose to Kissimmee?

    San Jose (SJC) is the airport you will fly out of if you book a flight from San Jose to Kissimmee. You should not have trouble finding flights to Kissimmee from San Jose; the airport handles an average of 0 outbound flights to Kissimmee per day. You should also have plenty of airline options to choose from since 7 airlines have flights from the San Jose airport to Kissimmee. It is only a 2.9 mi journey to San Jose (SJC) from San Jose’s city center.

  • How long is the flight from San Jose, California to Kissimmee?

    Alaska Airlines and Southwest can get you from San Jose, California to Kissimmee in just under 6h 50m. Your travel time can differ by up to 2h 09m. Airlines will cover a distance of 2415 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $84. Users have also found prices from $128 and $151 on Delta and American Airlines, respectively.

  • Can I find deals for flights from San Jose to Kissimmee that include hotel bookings?

    Yes. In addition to deals on San Jose to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Kissimmee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Kissimmee.

  • Can I find deals for business class flights from San Jose to Kissimmee?

    Yes. Cheapflights offers flight deals from San Jose 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 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 $233). 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

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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 April 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$139Average$320FlexibilityNo cancel feeOn-time65%
FrontierCheapest$214Average$320FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$256Average$425FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$267Average$457FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$270Average$463FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$276Average$413FlexibilityNo cancel feeOn-time69%
DeltaCheapest$276Average$434FlexibilityNo cancel feeOn-timeN/A

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