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Puerto Rico

$80+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Jun 18 — Jun 251
Thu 6/18
Thu 6/25
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 May 19, 2026.

This Super.com deal was found by Cheapflights users on 5/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:13 pm
MCO
-
SJU
Nonstop2h 58m
Frontier
Tue 8/116:31 pm
SJU
-
MCO
Nonstop3h 12m
Frontier
Deal found 5/15$200
This Super.com deal was found by Cheapflights users on 5/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:15 am
MCO
-
SJU
1 stop21h 42m
Frontier
Wed 6/248:50 am
SJU
-
MCO
1 stop13h 05m
Frontier
Deal found 5/15$206
This Super.com deal was found by Cheapflights users on 5/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:38 am
MCO
-
SJU
1 stop7h 55m
Frontier
Wed 7/85:15 pm
SJU
-
MCO
1 stop13h 29m
Frontier
Deal found 5/15$208
This Frontier deal was found by Cheapflights users on 5/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:51 pm
MCO
-
SJU
1 stop7h 53m
Frontier
Wed 8/266:25 am
SJU
-
MCO
1 stop9h 13m
Frontier
Deal found 5/17$211
This Super.com deal was found by Cheapflights users on 5/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:00 pm
MCO
-
SJU
1 stop23h 42m
Frontier
Wed 8/55:15 pm
SJU
-
MCO
1 stop13h 29m
Frontier
Deal found 5/14$213
This Cheapflightsfares deal was found by Cheapflights users on 5/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:18 am
MCO
-
SJU
1 stop7h 07m
Frontier
Tue 9/81:59 am
SJU
-
MCO
1 stop18h 41m
Frontier
Deal found 5/18$214
This Super.com deal was found by Cheapflights users on 5/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:01 pm
MCO
-
SJU
1 stop9h 43m
Frontier
Sat 7/119:00 am
SJU
-
MCO
1 stop13h 01m
Frontier
Deal found 5/15$215
This Frontier deal was found by Cheapflights users on 5/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:10 am
MCO
-
SJU
1 stop8h 15m
Frontier
Mon 9/281:59 am
SJU
-
MCO
1 stop8h 26m
Frontier
Deal found 5/18$216
This Trip.com deal was found by Cheapflights users on 5/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2211:13 pm
MCO
-
SJU
Nonstop2h 58m
Frontier
Wed 8/126:31 pm
SJU
-
MCO
Nonstop3h 12m
Frontier
Deal found 5/15$217
This Trip.com deal was found by Cheapflights users on 5/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/111:15 pm
MCO
-
SJU
Nonstop2h 54m
Frontier
Wed 7/85:15 pm
SJU
-
MCO
1 stop13h 29m
Frontier
Deal found 5/15$218
This Frontier deal was found by Cheapflights users on 5/14. 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.
Thu 9/311:12 pm
MCO
-
BQN
Nonstop2h 52m
Frontier
Mon 9/72:59 am
BQN
-
MCO
Nonstop2h 53m
Frontier
Deal found 5/14$221
This Priceline deal was found by Cheapflights users on 5/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:45 am
MCO
-
PSE
Nonstop3h 01m
Frontier
Mon 8/1710:31 am
PSE
-
MCO
Nonstop3h 07m
Frontier
Deal found 5/16$225

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 May 19, 2026.

Round-trip from

$200
(Super.com)

One-way from

$80
(Super.com)

Popular in

December

Cheapest in

February

Average price

$277
From Kissimmee to Puerto Rico
Search Deals
One-way flight from Kissimmee to Puerto Rico
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 19, 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

Fri 9/11

5:45 am-8:38 am

Nonstop2h 53m

Ponce Mercedita

Mon 9/14

9:30 am-12:35 pm

Nonstop3h 05m

$303

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 11/5

5:45 am-9:37 am

Nonstop2h 52m

Ponce Mercedita

Tue 11/10

10:30 am-12:42 pm

Nonstop3h 12m

$318

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 11/6

5:45 am-9:37 am

Nonstop2h 52m

Ponce Mercedita

Sat 11/14

10:30 am-12:42 pm

Nonstop3h 12m

$318

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 8/31

6:55 am-9:52 am

Nonstop2h 57m

Ponce Mercedita

Fri 9/4

10:37 am-1:59 pm

Nonstop3h 22m

$323

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 8/31

6:55 am-9:52 am

Nonstop2h 57m

Ponce Mercedita

Fri 9/4

5:01 am-12:07 pm

1 stop7h 06m

$342

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Thu 8/6

2:50 pm-5:55 pm

Nonstop3h 05m

San Juan Luis Munoz Marin Intl

Wed 8/12

3:59 pm-7:05 pm

Nonstop3h 06m

$345

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 8/20

5:01 am-7:56 am

Nonstop2h 55m

Ponce Mercedita

Thu 8/27

5:01 am-12:07 pm

1 stop7h 06m

$353

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sat 8/22

1:55 pm-4:56 pm

Nonstop3h 01m

Ponce Mercedita

Thu 8/27

5:01 am-12:07 pm

1 stop7h 06m

$353

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 8/17

5:01 am-7:56 am

Nonstop2h 55m

Ponce Mercedita

Tue 8/25

5:01 am-12:07 pm

1 stop7h 06m

$357

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 6/4

6:10 am-9:07 am

Nonstop2h 57m

Ponce Mercedita

Mon 6/8

10:02 am-1:23 pm

Nonstop3h 21m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/17

Showing 1-10 of 60 resultsSorted by cheapest first
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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 May 19, 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 May 16, 2026.

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. Saturday 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 May 19, 2026.

The most flights from K1S to PR0 are scheduled on a Monday (25 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 May 19, 2026.
Read through reviews of airlines operating flights from Kissimmee to Puerto Rico, such as Southwest,JetBlue, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,284 reviews

Overall

7.9

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,284 reviews
Southwest
7.9
Good
4,284 reviews

Overall

7.9

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,983 reviews
Southwest
7.9
Good
4,284 reviews

Overall

7.9

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,645 reviews
Southwest
7.9
Good
4,284 reviews

Overall

7.9

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.2
Okay
8,612 reviews
Southwest
7.9
Good
4,284 reviews

Overall

7.9

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,945 reviews
Southwest
7.9
Good
4,284 reviews

Overall

7.9

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 53m. JetBlue provides one of the quickest options available for as low as $303. 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 Spirit Airlines and JetBlue, with prices starting from $71 and $115, 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: Aer Lingus (85%), Azul (84%), JetBlue (81%).

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

    On average you can expect to pay $245 for a flight from Kissimmee to Puerto Rico. The cheapest flight overall is $76 while the most popular route, (Orlando - San Juan Luis Munoz Marin Intl) is currently priced at $250.

  • 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

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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 7 airlines flying from Kissimmee to Puerto Rico

Discover the top 7 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 May 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$222FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$98Average$228FlexibilityNo cancel feeOn-time65%
FrontierCheapest$107Average$252FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$139Average$388FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$229Average$374FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$244Average$360FlexibilityNo cancel feeOn-time63%
DeltaCheapest$253Average$313FlexibilityNo cancel feeOn-timeN/A

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