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Puerto Rico

$85+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Jul 22 — Jul 291
Wed 7/22
Wed 7/29
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 June 22, 2026.

This Priceline deal was found by Cheapflights users on 6/20. 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 10/2110:18 am
MCO
-
SJU
Nonstop2h 58m
Frontier
Wed 10/286:05 am
SJU
-
MCO
Nonstop3h 08m
Frontier
Deal found 6/20$231
This Orbitz deal was found by Cheapflights users on 6/20. 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.
Fri 9/186:55 am
MCO
-
SJU
1 stop8h 24m
Frontier
Mon 9/216:42 pm
SJU
-
MCO
Nonstop3h 10m
Frontier
Deal found 6/20$232
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2111:15 pm
MCO
-
SJU
Nonstop2h 54m
Frontier
Thu 6/259:24 am
SJU
-
MCO
Nonstop3h 09m
Frontier
Deal found 6/17$233
This eDestinos deal was found by Cheapflights users on 6/21. 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 6/3011:15 pm
MCO
-
SJU
Nonstop2h 54m
Frontier
Mon 7/68:37 pm
SJU
-
MCO
Nonstop3h 09m
Frontier
Deal found 6/21$234
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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.
Thu 8/278:05 am
MCO
-
SJU
Nonstop3h 01m
Frontier
Mon 8/316:44 am
SJU
-
MCO
1 stop13h 32m
Frontier
Deal found 6/21$235
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 8/216:58 am
MCO
-
SJU
1 stop20h 01m
Frontier
Sun 8/233:10 am
SJU
-
MCO
Nonstop3h 00m
Frontier
Deal found 6/19$236
This Frontier deal was found by Cheapflights users on 6/21. 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.
Wed 7/2911:17 pm
MCO
-
BQN
Nonstop2h 53m
Frontier
Sun 8/23:10 am
BQN
-
MCO
Nonstop2h 51m
Frontier
Deal found 6/21$237
This Frontier deal was found by Cheapflights users on 6/20. 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 8/88:59 pm
MCO
-
SJU
1 stop9h 45m
Frontier
Thu 8/208:57 pm
SJU
-
MCO
Nonstop3h 00m
Frontier
Deal found 6/20$237
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 7/258:40 am
MCO
-
BQN
Nonstop2h 54m
Frontier
Sat 8/83:10 am
BQN
-
MCO
Nonstop2h 51m
Frontier
Deal found 6/21$238
This Trip.com deal was found by Cheapflights users on 6/18. 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.
Tue 8/42:21 pm
MCO
-
SJU
Nonstop3h 10m
Frontier
Fri 8/78:37 pm
SJU
-
MCO
Nonstop3h 00m
Frontier
Deal found 6/18$238
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 7/2711:17 pm
MCO
-
BQN
Nonstop2h 53m
Frontier
Sat 8/812:19 pm
BQN
-
MCO
Nonstop3h 01m
Frontier
Deal found 6/21$239
This Super.com deal was found by Cheapflights users on 6/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:15 am
MCO
-
SJU
Nonstop2h 56m
Frontier
Sat 9/123:00 am
SJU
-
MCO
Nonstop3h 00m
Frontier
Deal found 6/20$239

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 June 22, 2026.

Round-trip from

$231
(Priceline)

One-way from

$85
(Super.com)

Popular in

December

Cheapest in

February

Average price

$336
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 June 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 June 22, 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

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Thu 9/10

12:15 pm-10:50 pm

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Tue 9/15

6:00 am-10:00 pm

2 stops16h 00m

$268

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Mon 8/10

12:45 pm-10:50 pm

1 stop10h 05m

San Juan Luis Munoz Marin Intl

Mon 8/17

5:45 pm-8:45 pm

Nonstop3h 00m

$282
Quickest round-trip

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Tue 8/18

3:05 pm-6:03 pm

Nonstop2h 58m

Aguadilla Borinquen

Wed 8/19

8:39 am-11:33 am

Nonstop2h 54m

$283

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Tue 8/18

5:01 am-7:58 am

Nonstop2h 57m

Ponce Mercedita

Thu 8/20

8:48 am-11:51 am

Nonstop3h 03m

$283

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Thu 10/22

5:20 pm-12:35 am

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Mon 10/26

5:30 am-4:05 pm

2 stops10h 35m

$304

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Wed 11/18

6:05 am-9:55 am

Nonstop2h 50m

San Juan Luis Munoz Marin Intl

Sat 11/21

2:15 pm-9:50 pm

1 stop8h 35m

$317

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 8/31

6:24 pm-11:59 pm

1 stop5h 35m

Ponce Mercedita

Fri 9/4

10:47 am-1:54 pm

Nonstop3h 07m

$318

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Sun 10/18

2:05 pm-12:15 am

2 stops10h 10m

San Juan Luis Munoz Marin Intl

Thu 10/22

5:30 am-5:10 pm

2 stops11h 40m

$321

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Wed 8/19

11:55 am-10:00 pm

2 stops10h 05m

San Juan Luis Munoz Marin Intl

Sun 8/23

6:00 am-6:15 pm

2 stops12h 15m

$321

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 8/31

5:01 am-7:56 am

Nonstop2h 55m

Ponce Mercedita

Tue 9/29

9:30 am-12:35 pm

Nonstop3h 05m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
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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 June 22, 2026.

It’s optimal to fly from Kissimmee to Puerto Rico in the evening. By choosing this option you can save up to 26% on the cost of your flight, compared to a flight in the morning.

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 June 22, 2026.

The most flights from K1S to PR0 are scheduled on a Sunday (34 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (18 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 20, 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 June 22, 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
4,242 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

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
4,242 reviews
Southwest
7.9
Good
4,242 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

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
11,737 reviews
Southwest
7.9
Good
4,242 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

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
2,996 reviews
Southwest
7.9
Good
4,242 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

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
2,872 reviews
Southwest
7.9
Good
4,242 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

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 58m. Southwest provides one of the quickest options available for as low as $283. 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?

    $61 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 - Aguadilla Borinquen and Orlando - Ponce Mercedita.

  • 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 $277 for a flight from Kissimmee to Puerto Rico. The cheapest flight overall is $138 while the most popular route, (Orlando - San Juan Luis Munoz Marin Intl) is currently priced at $209.

  • 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Orlando to Santo Domingo flights
Orlando to Punta Cana flights
Miami to Luis Munoz Marin Intl flights
Fort Lauderdale to Montego Bay flights
Fort Lauderdale to Santo Domingo flights
Miami to Willemstad flights
Miami to Santo Domingo flights
Miami to Punta Cana flights
Fort Lauderdale to Punta Cana flights
Orlando to Montego Bay flights
Miami to Nassau flights
Fort Lauderdale to Kingston flights
Jacksonville to Luis Munoz Marin Intl flights
Orlando to Aguadilla flights
Miami to Havana flights
Fort Lauderdale to Nassau flights
Orlando to Santiago de los Caballeros flights
Orlando to Ponce flights
Miami to Port of Spain flights
Miami to Providenciales flights
Miami to Oranjestad flights
Miami to Montego Bay flights
Orlando to Nassau flights
Miami to Simpson Bay flights
Fort Lauderdale to Santiago de los Caballeros flights
Miami to Santiago de los Caballeros flights
West Palm Beach to Luis Munoz Marin Intl flights
Miami to Kingston flights
Orlando to Oranjestad flights
Tampa to Punta Cana flights
Fort Lauderdale to Oranjestad flights
Orlando to Saint Thomas Island flights
Tampa to Santo Domingo flights
Miami to Bridgetown flights
Miami to Cap Haitien flights
Miami to Saint Thomas Island flights
Fort Lauderdale to Cap Haitien flights
Orlando to Providenciales flights
Miami to Castries flights
Miami to Georgetown flights
Tampa to Oranjestad flights
Miami to St. John's flights
Tampa to Montego Bay flights
Orlando to Port of Spain flights

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 June 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$222FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$109Average$259FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$145Average$363FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$226Average$370FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$244Average$363FlexibilityNo cancel feeOn-time63%

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