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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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
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 December 3, 2025.

This eDestinos deal was found by Cheapflights users on 12/1. 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.
Thu 12/1111:00 pmMCO - SJU
Nonstop2h 50mMultiple Airlines
Sat 12/131:32 pmSJU - MCO
Nonstop3h 16mMultiple Airlines
Deal found 12/1$147
This Cheapflightsfares deal was found by Cheapflights users on 12/1. 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 12/128:23 pmMCO - SJU
Nonstop2h 53mSpirit Airlines
Sat 12/134:10 amSJU - MCO
1 stop4h 35mSpirit Airlines
Deal found 12/1$149
This Frontier deal was found by Cheapflights users on 11/30. 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.
Mon 12/811:15 pmMCO - BQN
Nonstop2h 43mFrontier
Mon 12/156:42 pmBQN - MCO
Nonstop3h 11mFrontier
Deal found 11/30$150
This eDestinos deal was found by Cheapflights users on 11/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:00 amMCO - SJU
Nonstop2h 55mFrontier
Sat 12/133:55 amSJU - MCO
Nonstop3h 10mFrontier
Deal found 11/30$152
This Cheapflightsfares deal was found by Cheapflights users on 12/1. 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 12/1011:00 pmMCO - SJU
Nonstop2h 50mFrontier
Sat 12/1311:05 amSJU - MCO
Nonstop3h 22mFrontier
Deal found 12/1$154
This Super.com deal was found by Cheapflights users on 12/1. 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 12/1011:00 pmMCO - SJU
Nonstop2h 50mFrontier
Sun 12/141:59 amSJU - MCO
1 stop9h 55mFrontier
Deal found 12/1$155
This Expedia deal was found by Cheapflights users on 12/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/98:23 pmMCO - SJU
Nonstop2h 53mSpirit Airlines
Fri 12/125:00 pmSJU - MCO
Nonstop3h 18mSpirit Airlines
Deal found 12/2$156
This Super.com deal was found by Cheapflights users on 12/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:05 amMCO - SJU
1 stop7h 50mSpirit Airlines
Sat 12/61:32 pmSJU - MCO
Nonstop3h 16mSpirit Airlines
Deal found 12/2$160
This Priceline deal was found by Cheapflights users on 11/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/911:00 pmMCO - SJU
Nonstop2h 50mMultiple Airlines
Fri 12/126:59 pmSJU - MCO
1 stop14h 15mMultiple Airlines
Deal found 11/30$161
This Cheapflightsfares deal was found by Cheapflights users on 12/2. 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.
Thu 12/1111:00 pmMCO - SJU
Nonstop2h 50mFrontier
Fri 12/123:55 amSJU - MCO
Nonstop3h 10mFrontier
Deal found 12/2$162
This Cheapflightsfares deal was found by Cheapflights users on 12/1. 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 12/1011:00 pmMCO - SJU
Nonstop2h 50mFrontier
Sat 12/133:55 amSJU - MCO
Nonstop3h 10mFrontier
Deal found 12/1$163
This eDestinos deal was found by Cheapflights users on 11/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:23 pmMCO - SJU
Nonstop2h 53mSpirit Airlines
Sat 12/136:00 amSJU - MCO
1 stop18h 49mSpirit Airlines
Deal found 11/30$164

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 December 3, 2025.

Round-trip from

$151
(Cheapflightsfares)

One-way from

$80
(Priceline)

Popular in

December

Cheapest in

February

Average price

$347
From Kissimmee to Puerto Rico
Search Deals
One-way flight from Kissimmee to Puerto Rico
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 3, 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

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Wed 1/28

7:43 pm-11:33 pm

Nonstop2h 50m

San Juan Luis Munoz Marin Intl

Sun 2/1

6:00 am-8:15 am

Nonstop3h 15m

$162

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 3/2

6:00 am-9:55 am

Nonstop2h 55m

Ponce Mercedita

Sun 3/8

10:50 am-2:14 pm

Nonstop3h 24m

$184

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 1/16

7:25 am-11:20 am

Nonstop2h 55m

Ponce Mercedita

Mon 1/19

12:14 pm-2:46 pm

Nonstop3h 32m

$195

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Fri 12/12

8:18 pm-12:01 am

Nonstop2h 43m

Aguadilla Borinquen

Tue 12/16

5:01 am-7:01 am

Nonstop3h 00m

$198

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Fri 12/12

11:00 pm-2:50 am

Nonstop2h 50m

San Juan Luis Munoz Marin Intl

Sat 12/13

3:55 am-6:05 am

Nonstop3h 10m

$203

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Mon 1/12

7:25 am-11:19 am

Nonstop2h 54m

Ponce Mercedita

Sat 1/17

1:00 pm-3:28 pm

Nonstop3h 28m

$209

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 12/26

10:07 pm-2:00 am

Nonstop2h 53m

Ponce Mercedita

Tue 12/30

6:01 am-8:13 am

Nonstop3h 12m

$212

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sat 2/7

11:00 am-2:53 pm

Nonstop2h 53m

Ponce Mercedita

Mon 2/9

3:50 pm-6:08 pm

Nonstop3h 18m

$212

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 2/13

9:15 pm-1:08 am

Nonstop2h 53m

Ponce Mercedita

Tue 2/17

6:00 am-8:13 am

Nonstop3h 13m

$212

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 2/12

9:15 pm-1:08 am

Nonstop2h 53m

Ponce Mercedita

Sat 2/14

3:15 am-5:27 am

Nonstop3h 12m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

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 December 3, 2025.

It’s optimal to fly from Kissimmee to Puerto Rico in the evening. By choosing this option you can save up to 48% 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 November 29, 2025.

Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday 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 December 3, 2025.

The most flights from K1S to PR0 are scheduled on a Tuesday (20 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 December 3, 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
4,253 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

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
11,045 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

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
2,900 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

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
8,157 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

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
5.8
Fair
3,093 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

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 43m. Spirit Airlines 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?

    $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 $62 and $106, 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: Spirit Airlines (89%), Frontier (88%), Azul (69%).

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

    On average you can expect to pay $208 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 $134.

  • 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
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Fort Lauderdale to Santiago de los Caballeros flights
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Tampa to Santo Domingo flights
Fort Lauderdale to Oranjestad flights
Tampa to Saint Thomas Island flights
Miami to St. John's flights
Miami to Kingston flights
West Palm Beach to Punta Cana flights
Orlando to Simpson Bay flights
Miami to Bridgetown flights
Miami to George Town flights
Tampa to Nassau flights
Miami to Puerto Plata 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 December 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$197FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$92Average$227FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$109Average$233FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$251FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$134Average$374FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$225Average$439FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$244Average$365FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$325Average$504FlexibilityNo cancel feeOn-time69%

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