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$72+ Cheap flights from Kissimmee, FL to Puerto Rico

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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Kissimmee to Puerto Rico

Keep the following information in mind while searching for Kissimmee to Puerto Rico flight deals. Data was last updated September 17, 2025.

Round-trip from

$122
(Priceline)

One-way from

$72
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$247
From Kissimmee to Puerto Rico
Search Deals
One-way flight from Kissimmee to Puerto Rico
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 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 Kissimmee to Puerto Rico

Cheapest flights from Kissimmee to Puerto Rico
Explore the most affordable flight options available from Kissimmee to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Sat 11/18:20 amMCO - PSE
Nonstop3h 00mFrontier
Mon 11/312:15 pmPSE - MCO
Nonstop3h 15mFrontier
Deal found 9/14$117
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:29 pmMCO - BQN
Nonstop2h 48mFrontier
Sun 11/23:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/15$122
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.
Wed 10/2211:16 pmMCO - BQN
Nonstop2h 48mFrontier
Sat 10/252:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/16$123
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.
Tue 10/1411:16 pmMCO - BQN
Nonstop2h 48mFrontier
Mon 10/202:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/16$125
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/811:16 pmMCO - BQN
Nonstop2h 48mFrontier
Sat 10/112:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/16$135
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.
Fri 11/1411:16 pmMCO - BQN
Nonstop2h 48mFrontier
Sat 11/153:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/15$137
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.
Sat 11/18:20 amMCO - PSE
Nonstop3h 00mFrontier
Sat 11/812:15 pmPSE - MCO
Nonstop3h 15mFrontier
Deal found 9/16$137
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.
Fri 10/1011:16 pmMCO - BQN
Nonstop2h 48mFrontier
Fri 10/172:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/16$138
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.
Wed 10/2911:29 pmMCO - BQN
Nonstop2h 48mFrontier
Sat 11/13:12 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/15$139
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/117:15 amMCO - BQN
Nonstop2h 53mFrontier
Thu 10/162:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/16$143
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:00 amMCO - PSE
Nonstop2h 55mFrontier
Sat 12/1310:50 amPSE - MCO
Nonstop3h 24mFrontier
Deal found 9/15$148
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.
Fri 10/246:19 amMCO - PSE
Nonstop2h 59mFrontier
Fri 10/3112:15 pmPSE - MCO
Nonstop3h 15mFrontier
Deal found 9/15$149

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee to Puerto Rico 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 Kissimmee to Puerto Rico that are best for you.

Fly from

Kissimmee

Fly to

Puerto Rico

Route

Depart

Return

Price

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sat 11/1

8:20 am-11:20 am

Nonstop3h 00m

Ponce Mercedita

Mon 11/3

12:15 pm-2:30 pm

Nonstop3h 15m

$117

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sat 12/6

6:00 am-9:55 am

Nonstop2h 55m

Ponce Mercedita

Sat 12/13

10:50 am-1:14 pm

Nonstop3h 24m

$137

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 10/24

6:19 am-9:18 am

Nonstop2h 59m

Ponce Mercedita

Fri 10/31

12:15 pm-3:30 pm

Nonstop3h 15m

$149

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sat 11/1

8:20 am-11:20 am

Nonstop3h 00m

Ponce Mercedita

Sat 11/8

12:15 pm-2:30 pm

Nonstop3h 15m

$154

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 11/10

7:20 am-11:20 am

Nonstop3h 00m

Ponce Mercedita

Fri 11/14

12:15 pm-2:30 pm

Nonstop3h 15m

$157

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 10/24

6:19 am-9:18 am

Nonstop2h 59m

Ponce Mercedita

Mon 10/27

10:13 am-1:26 pm

Nonstop3h 13m

$191

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 10/17

6:19 am-9:18 am

Nonstop2h 59m

Ponce Mercedita

Mon 10/20

10:44 am-1:57 pm

Nonstop3h 13m

$191

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 11/14

7:20 am-11:20 am

Nonstop3h 00m

Ponce Mercedita

Mon 11/17

12:15 pm-2:30 pm

Nonstop3h 15m

$195

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Wed 10/29

9:55 pm-12:40 am

Nonstop2h 45m

Aguadilla Borinquen

Sun 11/2

4:00 am-5:57 am

Nonstop2h 57m

$198

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 12/5

6:00 am-9:55 am

Nonstop2h 55m

Ponce Mercedita

Sat 12/13

10:50 am-1:14 pm

Nonstop3h 24m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
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Best time to book a flight from Kissimmee to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Kissimmee 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 Kissimmee to Puerto Rico

What is the cheapest month to book a flight from Kissimmee to Puerto Rico?

Currently, September is the cheapest month in which you can book a flight from Kissimmee to Puerto Rico (average of $254). Flying from Kissimmee to Puerto Rico in June is currently the most expensive (average of $339). 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 K1S to PR?

Find hourly flight availability from Kissimmee to Puerto Rico. 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.

When flying from Kissimmee to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Kissimmee to Puerto Rico?

Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Puerto Rico. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Sunday at noon when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Kissimmee to Puerto Rico

Explore weekly flight availability from Kissimmee to Puerto Rico. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 17, 2025.

The most flights from K1S to PR0 are scheduled on a Monday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated September 17, 2025.
Read through reviews of airlines operating flights from Kissimmee to Puerto Rico, such as Southwest, American Airlines, and JetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,914 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Kissimmee to Puerto Rico?

    A quick flight from Kissimmee to Puerto Rico can take about 2h 45m. Frontier provides one of the quickest options available for as low as $198. There are 1128 mi between Kissimmee and Puerto Rico. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Kissimmee to Puerto Rico one-way?

    $79 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and Southwest, with prices starting from $96 and $122, respectively.

  • What are the most popular routes from Kissimmee to Puerto Rico?

    The most popular flight routes from Kissimmee to Puerto Rico are Orlando - San Juan Luis Munoz Marin Intl, Orlando - Ponce Mercedita and Orlando - Aguadilla Borinquen.

  • What are the most reliable airlines from Kissimmee to Puerto Rico?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Kissimmee to Puerto Rico on time: Azul (75%), JetBlue (75%), Frontier (65%).

  • What are the cheapest flights from Kissimmee to Puerto Rico?

    On average you can expect to pay $317 for a flight from Kissimmee to Puerto Rico. The cheapest flight overall is $85 while the most popular route, (Orlando - San Juan Luis Munoz Marin Intl) is currently priced at $173.

  • Can I find deals for flights from Kissimmee to Puerto Rico that include hotel bookings?

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

  • How can I find direct flights from Kissimmee to Puerto Rico?

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

  • Can I find deals for business class flights from Kissimmee to Puerto Rico?

    Yes. Cheapflights offers flight deals from Kissimmee to Puerto Rico 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 Kissimmee to Puerto Rico?

    Currently, September is the cheapest month in which you can book a flight from Kissimmee to Puerto Rico (average of $254). Flying from Kissimmee to Puerto Rico in June is currently the most expensive (average of $339). 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

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Alternative routes for Kissimmee to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Jacksonville to Montego Bay flights
Miami to St. George's flights
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Top 8 airlines flying from Kissimmee to Puerto Rico

Discover the top 8 airlines that operate flights from Kissimmee to Puerto Rico. 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
Avelo AirlinesCheapest$66Average$195FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$90Average$219FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$106Average$231FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$333FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$131Average$421FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$225Average$392FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$243Average$366FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$325Average$456FlexibilityNo cancel feeOn-time69%

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