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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 15 — Oct 221
Wed 10/15
Wed 10/22
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 15, 2025.

Round-trip from

$117
(Cheapflightsfares)

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 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/36:30 amMCO - PSE
Nonstop3h 00mFrontier
Sun 10/510:15 amPSE - MCO
Nonstop3h 11mFrontier
Deal found 9/13$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 Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:16 pmMCO - BQN
Nonstop2h 48mFrontier
Sun 11/163:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/14$125
This Trip.com deal was found by Cheapflights users on 9/13. 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 10/26:30 amMCO - PSE
Nonstop3h 00mFrontier
Sun 10/510:15 amPSE - MCO
Nonstop3h 11mFrontier
Deal found 9/13$129
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/26:30 amMCO - PSE
Nonstop3h 00mFrontier
Fri 10/310:15 amPSE - MCO
Nonstop3h 11mFrontier
Deal found 9/13$130
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.
Sun 9/216:30 amMCO - PSE
Nonstop3h 00mFrontier
Sun 9/2810:15 amPSE - MCO
Nonstop3h 11mFrontier
Deal found 9/14$132
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1711:16 pmMCO - BQN
Nonstop2h 48mFrontier
Tue 10/212:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/14$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 9/14. 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.
Wed 10/2911:29 pmMCO - BQN
Nonstop2h 48mFrontier
Fri 11/73:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/14$139
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1211:16 pmMCO - BQN
Nonstop2h 48mFrontier
Sat 11/153:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/14$143
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2711:35 pmMCO - BQN
Nonstop2h 52mFrontier
Fri 10/33:32 amBQN - MCO
Nonstop2h 58mFrontier
Deal found 9/14$146
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/2411:35 pmMCO - BQN
Nonstop2h 52mFrontier
Mon 10/273:29 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 9/13$148

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 15, 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

Fri 10/3

6:30 am-9:30 am

Nonstop3h 00m

Ponce Mercedita

Sun 10/5

10:15 am-1:26 pm

Nonstop3h 11m

$117

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

Thu 10/2

6:30 am-9:30 am

Nonstop3h 00m

Ponce Mercedita

Fri 10/3

10:15 am-1:26 pm

Nonstop3h 11m

$130

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 9/26

6:30 am-9:30 am

Nonstop3h 00m

Ponce Mercedita

Sun 9/28

10:15 am-1:26 pm

Nonstop3h 11m

$132

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sun 9/21

6:30 am-9:30 am

Nonstop3h 00m

Ponce Mercedita

Sun 9/28

10:15 am-1:26 pm

Nonstop3h 11m

$132

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 9/26

6:30 am-9:30 am

Nonstop3h 00m

Ponce Mercedita

Fri 10/3

10:15 am-1:26 pm

Nonstop3h 11m

$154

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

$168

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 10/3

7:59 pm-10:56 pm

Nonstop2h 57m

Ponce Mercedita

Mon 10/6

5:20 am-8:26 am

Nonstop3h 06m

$187

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 10/3

6:30 am-9:30 am

Nonstop3h 00m

Ponce Mercedita

Mon 10/6

10:15 am-1:26 pm

Nonstop3h 11m

$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

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 15, 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 7, 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 15, 2025.

The most flights from K1S to PR0 are scheduled on a Monday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 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 15, 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

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
2,912 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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. Generally, flights for this route are nonstop.

  • 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 $116 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: JetBlue (75%), Azul (74%), Frontier (60%).

  • 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 $157.

  • 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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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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$195FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$89Average$236FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$104Average$230FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$333FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$130Average$419FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$225Average$391FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$242Average$367FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$325Average$456FlexibilityNo cancel feeOn-time69%

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