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Puerto Rico

$87+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Aug 1 — Aug 81
Sat 8/1
Sat 8/8
1 adult, Economy
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Cheap 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 July 2, 2026.

This Priceline deal was found by Cheapflights users on 6/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:55 pm
MCO
-
SJU
Nonstop2h 55m
Frontier
Sat 10/101:59 am
SJU
-
MCO
1 stop18h 41m
Frontier
Deal found 6/29$237
This eDestinos deal was found by Cheapflights users on 6/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2111:17 pm
MCO
-
SJU
Nonstop2h 58m
Frontier
Mon 7/2710:48 pm
SJU
-
MCO
Nonstop3h 09m
Frontier
Deal found 6/28$239
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Mon 9/282:36 pm
MCO
-
SJU
Nonstop3h 01m
Frontier
Thu 10/296:31 pm
SJU
-
MCO
Nonstop3h 12m
Frontier
Deal found 6/27$240
This eDestinos deal was found by Cheapflights users on 6/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:38 am
MCO
-
SJU
1 stop14h 45m
Frontier
Wed 7/225:45 pm
SJU
-
MCO
1 stop25h 26m
Frontier
Deal found 6/27$241
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 9/2710:55 pm
MCO
-
SJU
Nonstop2h 55m
Frontier
Thu 10/299:03 am
SJU
-
MCO
Nonstop3h 10m
Frontier
Deal found 6/27$242
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Fri 10/25:05 am
MCO
-
SJU
Nonstop2h 53m
Frontier
Mon 10/262:55 am
SJU
-
MCO
Nonstop3h 03m
Frontier
Deal found 6/27$243
This Frontier deal was found by Cheapflights users on 6/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:17 pm
MCO
-
BQN
Nonstop2h 53m
Frontier
Tue 8/43:10 am
BQN
-
MCO
Nonstop2h 51m
Frontier
Deal found 6/28$244
This Trip.com deal was found by Cheapflights users on 6/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:01 am
MCO
-
SJU
1 stop13h 48m
Frontier
Tue 9/812:11 pm
SJU
-
MCO
Nonstop3h 14m
Frontier
Deal found 6/29$244
This Frontier deal was found by Cheapflights users on 6/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:17 pm
MCO
-
BQN
Nonstop2h 53m
Frontier
Sun 9/612:04 pm
BQN
-
MCO
Nonstop3h 01m
Frontier
Deal found 6/27$246
This eDestinos deal was found by Cheapflights users on 6/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:30 am
MCO
-
SJU
1 stop16h 37m
Frontier
Tue 7/213:36 pm
SJU
-
MCO
1 stop27h 52m
Frontier
Deal found 6/28$246
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:05 am
MCO
-
SJU
Nonstop3h 01m
Frontier
Sat 9/126:31 pm
SJU
-
MCO
Nonstop3h 12m
Frontier
Deal found 7/2$247
This Frontier deal was found by Cheapflights users on 6/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:45 pm
MCO
-
SJU
Nonstop2h 59m
Frontier
Fri 10/162:58 am
SJU
-
MCO
Nonstop3h 03m
Frontier
Deal found 6/30$248

Find 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 July 2, 2026.

Round-trip from

$237
(Priceline)

One-way from

$87
(Frontier)

Popular in

December

Cheapest in

February

Average price

$311
From Kissimmee to Puerto Rico
Search Deals
One-way flight from Kissimmee to Puerto Rico
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 2, 2026.
Use the filters below to find and compare flights from Kissimmee to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 8/31

5:01 am-7:58 am

Nonstop2h 57m

Ponce Mercedita

Tue 9/1

5:01 am-11:02 am

1 stop6h 01m

$305

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Wed 8/26

6:24 pm-12:33 am

1 stop6h 09m

Aguadilla Borinquen

Thu 8/27

6:55 pm-9:53 pm

Nonstop2h 58m

$310

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 8/20

6:24 pm-11:59 pm

1 stop5h 35m

Ponce Mercedita

Mon 8/24

8:48 am-11:51 am

Nonstop3h 03m

$318

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 8/7

5:01 am-7:58 am

Nonstop2h 57m

Ponce Mercedita

Mon 8/10

5:01 am-11:02 am

1 stop6h 01m

$318

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Wed 7/22

5:45 am-8:43 am

Nonstop2h 58m

Ponce Mercedita

Wed 7/29

5:01 am-11:08 am

1 stop6h 07m

$320
Quickest round-trip

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Tue 9/8

5:01 am-7:56 am

Nonstop2h 55m

Ponce Mercedita

Tue 9/29

9:30 am-12:35 pm

Nonstop3h 05m

$323

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 8/27

5:01 am-7:58 am

Nonstop2h 57m

Ponce Mercedita

Sun 8/30

5:01 am-11:02 am

1 stop6h 01m

$327

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 12/3

7:15 pm-11:05 pm

Nonstop2h 50m

Ponce Mercedita

Sat 12/12

5:20 am-7:30 am

Nonstop3h 10m

$338

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Thu 9/24

10:00 am-11:05 pm

2 stops13h 05m

San Juan Luis Munoz Marin Intl

Mon 9/28

6:00 am-4:45 pm

2 stops10h 45m

$346

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Sat 9/5

1:35 pm-9:55 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Tue 9/8

6:00 am-10:00 pm

2 stops16h 00m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/27

Showing 1-10 of 60 resultsSorted by cheapest first
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2
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6

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 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 July 2, 2026.

It’s optimal to fly from Kissimmee to Puerto Rico in the evening. By choosing this option you can save up to 17% on the cost of your flight, compared to a flight in the afternoon.

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 July 2, 2026.

The most flights from K1S to PR0 are scheduled on a Thursday (30 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).

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 June 27, 2026.

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

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 July 2, 2026.
Read through reviews of airlines operating flights from Kissimmee to Puerto Rico, such as Southwest,American Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,769 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
JetBlue
7.1
Good
3,009 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,850 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 57m. Frontier provides one of the quickest options available for as low as $255. There are 1178 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?

    $62 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 American Airlines, with prices starting from $116 and $126, 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 (91%), JetBlue (90%), Aer Lingus (89%).

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

    On average you can expect to pay $268 for a flight from Kissimmee to Puerto Rico. The cheapest flight overall is $126 while the most popular route, (Orlando - San Juan Luis Munoz Marin Intl) is currently priced at $221.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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.
Orlando to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
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Miami to Santiago de los Caballeros flights
Miami to Bridgetown flights
Orlando to Saint Thomas Island flights
Tampa to Santo Domingo flights
Orlando to Oranjestad flights
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Miami to Cap Haitien flights
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Fort Lauderdale to Cap Haitien flights
Tampa to Oranjestad flights
Miami to St. John's flights
Tampa to Nassau flights
Miami to Castries flights
Fort Lauderdale to Aguadilla flights
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Top 5 airlines flying from Kissimmee to Puerto Rico

Discover the top 5 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 July 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$222FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$109Average$266FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$146Average$363FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$226Average$372FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$244Average$364FlexibilityNo cancel feeOn-time63%

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