HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Puerto Rico

$77+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kissimmee to Puerto Rico with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 octubre 28, 2025.

This Frontier deal was found by Cheapflights users on 10/26. 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.
mié. 10/2911:29 pmMCO - BQN
Nonstop2h 48mFrontier
sáb. 11/13:12 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 10/26$151
This Frontier deal was found by Cheapflights users on 10/28. 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.
lun. 11/2411:15 pmMCO - BQN
Nonstop2h 48mFrontier
jue. 11/273:55 amBQN - MCO
Nonstop3h 06mFrontier
Deal found 10/28$160
This Frontier deal was found by Cheapflights users on 10/28. 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.
mar. 11/187:48 amMCO - SJU
1 stop9h 06mFrontier
dom. 11/2310:22 pmSJU - MCO
Nonstop3h 15mFrontier
Deal found 10/28$161
This Frontier deal was found by Cheapflights users on 10/26. 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.
mié. 10/2911:29 pmMCO - BQN
Nonstop2h 48mFrontier
dom. 11/23:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 10/26$163
This Frontier deal was found by Cheapflights users on 10/28. 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.
jue. 11/275:15 pmMCO - SJU
Nonstop2h 57mFrontier
jue. 12/410:42 amSJU - MCO
2 stops14h 53mFrontier
Deal found 10/28$164
This Frontier deal was found by Cheapflights users on 10/27. 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.
sáb. 11/111:29 pmMCO - BQN
Nonstop2h 48mFrontier
vie. 11/73:59 amBQN - MCO
Nonstop2h 59mFrontier
Deal found 10/27$167
This Frontier deal was found by Cheapflights users on 10/28. 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.
sáb. 11/811:00 pmMCO - SJU
Nonstop2h 54mFrontier
sáb. 11/2210:28 pmSJU - MCO
Nonstop3h 15mFrontier
Deal found 10/28$169
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
sáb. 11/2211:22 pmMCO - BQN
Nonstop2h 48mFrontier
lun. 11/243:55 amBQN - MCO
Nonstop3h 06mFrontier
Deal found 10/26$170
This Frontier deal was found by Cheapflights users on 10/28. 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.
sáb. 11/157:48 amMCO - SJU
1 stop9h 06mFrontier
dom. 11/233:59 amSJU - MCO
Nonstop3h 02mFrontier
Deal found 10/28$170
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/66:00 amMCO - PSE
Nonstop2h 55mFrontier
lun. 12/810:50 amPSE - MCO
Nonstop3h 24mFrontier
Deal found 10/28$170
This CheapOair deal was found by Cheapflights users on 10/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/1311:00 pmMCO - SJU
Nonstop2h 50mFrontier
sáb. 12/203:55 amSJU - MCO
Nonstop3h 10mFrontier
Deal found 10/27$171
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/46:00 amMCO - PSE
Nonstop2h 55mFrontier
sáb. 12/1310:50 amPSE - MCO
Nonstop3h 24mFrontier
Deal found 10/28$171

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 octubre 28, 2025.

Round-trip from

$154
(Frontier)

One-way from

$77
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$259
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 ($13 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 October 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 octubre 28, 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

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

vie. 12/5

6:00 am-9:55 am

Nonstop2h 55m

Ponce Mercedita

sáb. 12/13

10:50 am-1:14 pm

Nonstop3h 24m

$173

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

lun. 1/12

6:00 am-9:55 am

Nonstop2h 55m

Ponce Mercedita

vie. 1/16

10:50 am-1:17 pm

Nonstop3h 27m

$190

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

jue. 12/11

6:00 am-9:55 am

Nonstop2h 55m

Ponce Mercedita

lun. 12/15

10:50 am-1:14 pm

Nonstop3h 24m

$218

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

vie. 12/12

6:00 am-9:55 am

Nonstop2h 55m

Ponce Mercedita

sáb. 12/13

10:50 am-1:14 pm

Nonstop3h 24m

$218

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

jue. 11/20

11:50 pm-3:42 am

Nonstop2h 52m

Ponce Mercedita

dom. 11/23

5:01 am-7:11 am

Nonstop3h 10m

$227

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

vie. 12/5

6:00 am-9:55 am

Nonstop2h 55m

Ponce Mercedita

lun. 12/8

10:50 am-1:14 pm

Nonstop3h 24m

$228

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

vie. 12/5

8:18 pm-12:01 am

Nonstop2h 43m

Aguadilla Borinquen

dom. 12/14

5:01 am-7:01 am

Nonstop3h 00m

$230

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

mar. 11/25

11:55 pm-3:47 am

Nonstop2h 52m

Ponce Mercedita

mar. 12/2

5:20 am-7:30 am

Nonstop3h 10m

$232

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

vie. 10/31

8:20 am-11:20 am

Nonstop3h 00m

Ponce Mercedita

lun. 11/3

12:15 pm-2:30 pm

Nonstop3h 15m

$240

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

mar. 12/9

8:50 pm-12:35 am

Nonstop2h 45m

San Juan Luis Munoz Marin Intl

sáb. 12/13

7:50 pm-10:05 pm

Nonstop3h 15m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 60 results
1
2
3
...
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 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 $121). 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 octubre 28, 2025.

It’s optimal to fly from Kissimmee to Puerto Rico in the evening. By choosing this option you can save up to 49% 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 October 26, 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.

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 octubre 28, 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
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,033 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,907 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,112 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,122 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 45m. Frontier provides one of the quickest options available for as low as $244. There are 1188 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?

    $79 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 $114 and $116, 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: Frontier (78%), Spirit Airlines (76%), Azul (75%).

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

    On average you can expect to pay $218 for a flight from Kissimmee to Puerto Rico. The cheapest flight overall is $94 while the most popular route, (Orlando - San Juan Luis Munoz Marin Intl) is currently priced at $196.

  • 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 $121). 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

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
Tampa to Luis Munoz Marin Intl flights
Orlando to Punta Cana flights
Miami to Santo Domingo flights
Fort Lauderdale to Santo Domingo flights
Miami to Punta Cana flights
Fort Lauderdale to Punta Cana flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Miami to Luis Munoz Marin Intl flights
Miami to Nassau flights
Orlando to Santo Domingo flights
Orlando to Santiago de los Caballeros flights
Orlando to Ponce flights
Orlando to Aguadilla flights
Orlando to Montego Bay flights
Fort Lauderdale to Montego Bay flights
Miami to Cap Haitien flights
West Palm Beach to Luis Munoz Marin Intl flights
Jacksonville to Luis Munoz Marin Intl flights
Fort Lauderdale to Kingston flights
Miami to Simpson Bay flights
Miami to Havana flights
Miami to Willemstad flights
Fort Lauderdale to Nassau flights
Miami to Oranjestad flights
Orlando to Nassau flights
Miami to Port of Spain flights
Miami to Santiago de los Caballeros flights
Orlando to Oranjestad flights
Miami to Saint Thomas Island flights
Fort Lauderdale to Santiago de los Caballeros flights
Tampa to Santo Domingo flights
Miami to Providenciales flights
Miami to Bridgetown flights
Miami to Castries flights
Miami to Montego Bay flights
Tampa to Punta Cana flights
Fort Lauderdale to Saint Thomas Island flights
Orlando to Saint Thomas Island flights
Orlando to Port of Spain flights
West Palm Beach to Santo Domingo flights
Fort Lauderdale to Aguadilla flights
Miami to George Town flights
Miami to St. John's flights
Fort Lauderdale to Oranjestad flights
Tampa to Saint Thomas Island flights
Tampa to Montego Bay flights
Tampa to George Town flights
Fort Lauderdale to Port of Spain flights
Pensacola to Luis Munoz Marin Intl 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 octubre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$196FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$92Average$231FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$110Average$233FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$371FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$132Average$375FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$225Average$385FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$244Average$367FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$324Average$471FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.