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$68+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Round-trip from

$139
(Super.com)

One-way from

$68
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$242
From Kissimmee to Puerto Rico
Search Deals
One-way flight from Kissimmee to Puerto Rico
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This Super.com deal was found by Cheapflights users on 1/8. 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.
Wed 2/1811:15 pmMCO - BQN
Nonstop2h 42mFrontier
Mon 2/233:59 amBQN - MCO
Nonstop3h 01mFrontier
Deal found 1/8$139
This Frontier deal was found by Cheapflights users on 1/8. 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 2/2611:15 pmMCO - BQN
Nonstop2h 42mFrontier
Sat 2/283:58 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 1/8$140
This Frontier deal was found by Cheapflights users on 1/7. 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 3/2811:00 pmMCO - BQN
Nonstop2h 42mFrontier
Fri 4/33:55 amBQN - MCO
Nonstop3h 07mFrontier
Deal found 1/7$144
This Super.com deal was found by Cheapflights users on 1/6. 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.
Tue 2/1711:15 pmMCO - BQN
Nonstop2h 42mFrontier
Thu 2/193:58 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 1/6$152
This Orbitz deal was found by Cheapflights users on 1/8. 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 1/236:00 amMCO - SJU
Nonstop2h 47mMultiple Airlines
Mon 1/267:00 pmSJU - MCO
1 stop16h 54mMultiple Airlines
Deal found 1/8$153
This Super.com deal was found by Cheapflights users on 1/8. 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.
Fri 2/276:20 amMCO - PSE
Nonstop2h 50mFrontier
Mon 3/211:30 amPSE - MCO
Nonstop3h 25mFrontier
Deal found 1/8$153
This Frontier deal was found by Cheapflights users on 1/5. 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 1/3111:27 amMCO - SJU
Nonstop2h 59mFrontier
Sat 1/316:11 pmSJU - MCO
1 stop7h 20mFrontier
Deal found 1/5$154
This CheapOair deal was found by Cheapflights users on 1/6. 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.
Mon 1/127:10 amMCO - BQN
Nonstop2h 47mFrontier
Wed 1/143:48 amBQN - MCO
Nonstop3h 02mFrontier
Deal found 1/6$155
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/2111:27 amMCO - SJU
Nonstop2h 59mMultiple Airlines
Wed 1/284:40 pmSJU - MCO
1 stop8h 19mMultiple Airlines
Deal found 1/6$155
This CheapOair deal was found by Cheapflights users on 1/6. 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.
Fri 1/167:25 amMCO - PSE
Nonstop2h 55mFrontier
Sun 1/1812:14 pmPSE - MCO
Nonstop3h 32mFrontier
Deal found 1/6$155
This Frontier deal was found by Cheapflights users on 1/8. 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 2/1311:15 pmMCO - BQN
Nonstop2h 42mFrontier
Sun 2/153:58 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 1/8$156
This Super.com deal was found by Cheapflights users on 1/7. 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.
Fri 1/2311:37 amMCO - SJU
1 stop7h 47mSpirit Airlines
Tue 1/278:05 pmSJU - MCO
Nonstop3h 20mSpirit Airlines
Deal found 1/7$156

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 January 8, 2026.
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 2/27

6:20 am-10:10 am

Nonstop2h 50m

Ponce Mercedita

Mon 3/2

11:30 am-1:55 pm

Nonstop3h 25m

$159

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 2/27

6:20 am-10:10 am

Nonstop2h 50m

Ponce Mercedita

Sat 3/7

12:35 pm-3:07 pm

Nonstop3h 32m

$160

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 2/13

6:20 am-10:10 am

Nonstop2h 50m

Ponce Mercedita

Mon 2/16

11:45 am-2:10 pm

Nonstop3h 25m

$166

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 2/23

6:45 am-10:35 am

Nonstop2h 50m

Ponce Mercedita

Fri 2/27

11:00 am-1:25 pm

Nonstop3h 25m

$172

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sat 2/7

9:00 am-12:52 pm

Nonstop2h 52m

Ponce Mercedita

Mon 2/23

11:30 am-1:55 pm

Nonstop3h 25m

$181

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sat 3/7

7:45 am-11:40 am

Nonstop2h 55m

Ponce Mercedita

Tue 3/24

11:35 am-3:00 pm

Nonstop3h 25m

$183

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Wed 1/21

11:50 pm-3:30 am

Nonstop2h 40m

Aguadilla Borinquen

Tue 1/27

5:01 am-7:04 am

Nonstop3h 03m

$193

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 1/15

7:25 am-11:20 am

Nonstop2h 55m

Ponce Mercedita

Sun 1/18

12:14 pm-2:46 pm

Nonstop3h 32m

$200

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 3/27

9:59 pm-12:50 am

Nonstop2h 51m

Ponce Mercedita

Fri 4/3

6:52 pm-10:02 pm

Nonstop3h 10m

$213

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 3/27

9:59 pm-12:50 am

Nonstop2h 51m

Ponce Mercedita

Sun 4/5

6:52 pm-10:02 pm

Nonstop3h 10m

$213

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

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, August is the cheapest month in which you can book a flight from Kissimmee to Puerto Rico (average of $53). Flying from Kissimmee to Puerto Rico in December is currently the most expensive (average of $124). 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 January 8, 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.

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 January 3, 2026.

Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Tuesday at noon when fares are most often at their lowest. Saturday at noon 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 January 8, 2026.

The most flights from K1S to PR0 are scheduled on a Wednesday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 January 8, 2026.
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
4,250 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,097 reviews
Southwest
8.0
Very good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,892 reviews
Southwest
8.0
Very good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,289 reviews
Southwest
8.0
Very good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,061 reviews
Southwest
8.0
Very good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 40m. Frontier provides one of the quickest options available for as low as $193. 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?

    $59 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and JetBlue, with prices starting from $63 and $108, 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: Spirit Airlines (80%), Frontier (75%), Azul (74%).

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

    On average you can expect to pay $325 for a flight from Kissimmee to Puerto Rico. The cheapest flight overall is $81 while the most popular route, (Orlando - San Juan Luis Munoz Marin Intl) is currently priced at $118.

  • 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, August is the cheapest month in which you can book a flight from Kissimmee to Puerto Rico (average of $53). Flying from Kissimmee to Puerto Rico in December is currently the most expensive (average of $124). 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.
Orlando to Luis Munoz Marin Intl flights
Orlando to Punta Cana flights
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West Palm Beach to Punta Cana flights
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Miami to George Town flights
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Miami to Road Town flights
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Tampa to Nassau flights
Tampa to Oranjestad flights

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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$197FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$93Average$228FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$110Average$249FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$251FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$135Average$373FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$225Average$438FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$244Average$367FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$325Average$502FlexibilityNo cancel feeOn-time69%

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