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Kissimmee

$88+ Cheap flights from San Jose (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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MCO
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from San Jose to Kissimmee are usually found in January or May, booked 43 days in advance, depart on a Saturday or Friday and return on a Tuesday

Cheap 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 September 17, 2025.

Round-trip from

$212
(Booking.com)

One-way from

$88
(Trip.com)

Popular in

March

Cheapest in

January

Average price

$429
From San Jose to Kissimmee
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One-way flight from San Jose to Kissimmee
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Highest demand for flights based on searches. 11% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 17, 2025.

This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:27 pmSJC - MCO
1 stop14h 37mFrontier
Sun 10/266:00 amMCO - SJC
1 stop8h 32mFrontier
Deal found 9/16$212
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:43 pmSJC - MCO
1 stop8h 02mFrontier
Mon 11/36:00 amMCO - SJC
1 stop8h 32mFrontier
Deal found 9/16$220
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:27 pmSJC - MCO
1 stop14h 17mFrontier
Mon 11/108:00 amMCO - SJC
1 stop12h 34mFrontier
Deal found 9/16$232
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/206:43 pmSJC - MCO
1 stop8h 02mFrontier
Fri 10/246:00 amMCO - SJC
1 stop8h 32mFrontier
Deal found 9/15$237
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:51 amSJC - MCO
1 stop9h 24mMultiple Airlines
Thu 11/68:59 pmMCO - SJC
1 stop17h 33mMultiple Airlines
Deal found 9/15$251
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/512:26 pmSJC - MCO
1 stop14h 18mMultiple Airlines
Wed 10/810:00 amMCO - SJC
1 stop12h 06mMultiple Airlines
Deal found 9/16$257
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2912:25 pmSJC - MCO
1 stop9h 20mFrontier
Thu 10/26:00 amMCO - SJC
1 stop10h 14mFrontier
Deal found 9/16$258
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/111:40 amSJC - MCO
2 stops17h 20mMultiple Airlines
Sun 10/56:00 amMCO - SJC
1 stop8h 26mMultiple Airlines
Deal found 9/16$262
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/136:43 pmSJC - MCO
1 stop8h 02mFrontier
Mon 10/206:00 amMCO - SJC
1 stop8h 32mFrontier
Deal found 9/16$265
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:25 pmSJC - MCO
1 stop9h 20mFrontier
Sun 10/56:00 amMCO - SJC
1 stop8h 26mFrontier
Deal found 9/15$268
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:25 pmSJC - MCO
1 stop14h 19mFrontier
Mon 9/297:05 amMCO - SJC
1 stop13h 40mFrontier
Deal found 9/15$269

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 September 17, 2025.
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

Sat 10/25

6:25 am-4:50 pm

1 stop7h 25m

Orlando

Tue 10/28

7:00 am-1:45 pm

1 stop9h 45m

$292

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Mon 11/17

7:47 pm-7:40 am

1 stop8h 53m

Orlando

Wed 11/19

5:49 pm-10:37 pm

1 stop7h 48m

$292

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Thu 11/6

11:51 am-12:15 am

1 stop9h 24m

Orlando

Thu 11/13

9:00 am-3:54 pm

1 stop9h 54m

$292

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Wed 10/8

7:35 pm-7:21 am

1 stop8h 46m

Orlando

Wed 10/15

4:55 pm-11:40 pm

1 stop9h 45m

$293

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Wed 10/8

7:35 pm-7:21 am

1 stop8h 46m

Orlando

Thu 10/16

6:39 pm-11:40 pm

1 stop8h 01m

$293

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Sun 10/26

1:00 pm-11:05 pm

1 stop7h 05m

Orlando

Wed 10/29

2:50 pm-9:20 pm

2 stops9h 30m

$298

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Mon 10/13

8:55 pm-8:45 am

1 stop8h 50m

Orlando

Wed 10/22

2:50 pm-9:20 pm

2 stops9h 30m

$298

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Tue 3/3

9:05 am-11:39 pm

1 stop11h 34m

Orlando

Wed 3/4

7:00 am-4:20 pm

1 stop12h 20m

$325

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Tue 10/7

12:38 pm-12:19 am

1 stop8h 41m

Orlando

Thu 10/16

7:00 am-7:35 pm

2 stops15h 35m

$340

San JoseOrlando

SJC - MCO

SJCMCO

San Jose

Mon 10/6

10:29 am-12:19 am

1 stop10h 50m

Orlando

Wed 10/8

7:00 am-2:50 pm

1 stop10h 50m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 24 results
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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 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 September 12, 2025.

To ensure you get the cheapest price possible for a flight from San Jose to Kissimmee, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from San Jose to Kissimmee?

Currently, May is the cheapest month in which you can book a flight from San Jose to Kissimmee (average of $206). Flying from San Jose 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 SJC to K1S?

Find hourly flight availability from San Jose 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 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Jose to Kissimmee as you normally would.

What is the cheapest day to fly from San Jose to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from San Jose to Kissimmee. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their San Jose to Kissimmee flight should consider departing on Thursday at noon when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 17, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and American 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.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 to Kissimmee?

    For as low as $292, Alaska Airlines can have you in Kissimmee from San Jose in 7h 25m. Airlines will cover a distance of 2415 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 to Kissimmee?

    Currently, May is the cheapest month in which you can book a flight from San Jose to Kissimmee (average of $206). Flying from San Jose 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.

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$117Average$235FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$167Average$304FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$250Average$461FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$265Average$414FlexibilityNo cancel feeOn-time75%
DeltaCheapest$275Average$439FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$306Average$471FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$312Average$503FlexibilityNo cancel feeOn-time69%

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