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$95+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 June 30, 2025.

Round-trip from

$160
(SmartFares)

One-way from

$95
(eDestinos)

Popular in

December

Cheapest in

October

Average price

$256
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 ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 30, 2025.

This Frontier deal was found by Cheapflights users on 6/28. 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.
Wed 8/2011:55 pmMCO - BQN
Nonstop2h 49mFrontier
Tue 8/263:43 amBQN - MCO
Nonstop2h 54mFrontier
Deal found 6/28$164
This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2711:40 pmMCO - SJU
Nonstop2h 54mFrontier
Fri 10/31:11 amSJU - MCO
1 stop16h 52mFrontier
Deal found 6/28$168
This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/46:00 amMCO - SJU
1 stop8h 18mMultiple Airlines
Thu 8/710:14 pmSJU - MCO
1 stop11h 43mMultiple Airlines
Deal found 6/28$169
This eDestinos deal was found by Cheapflights users on 6/29. 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 7/156:50 amMCO - SJU
1 stop8h 40mSpirit Airlines
Tue 7/222:40 amSJU - MCO
Nonstop3h 07mSpirit Airlines
Deal found 6/29$171
This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/155:30 amMCO - PSE
Nonstop2h 56mFrontier
Mon 8/189:16 amPSE - MCO
Nonstop3h 11mFrontier
Deal found 6/28$198
This JetBlue deal was found by Cheapflights users on 6/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/711:20 amMCO - BQN
Nonstop2h 50mJetBlue
Mon 8/113:16 pmBQN - MCO
Nonstop2h 54mJetBlue
Deal found 6/30$232
This JetBlue deal was found by Cheapflights users on 6/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/265:05 amMCO - PSE
Nonstop2h 57mJetBlue
Mon 7/288:50 amPSE - MCO
Nonstop3h 03mJetBlue
Deal found 6/29$252
This JetBlue deal was found by Cheapflights users on 6/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/248:00 amMCO - MAZ
1 stop5h 27mJetBlue
Mon 7/285:00 pmMAZ - MCO
1 stop7h 47mJetBlue
Deal found 6/29$461
This JetBlue deal was found by Cheapflights users on 6/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:15 amMCO - CPX
1 stop5h 56mJetBlue
Sun 9/283:05 pmCPX - MCO
1 stop4h 45mJetBlue
Deal found 6/29$487
This JetBlue deal was found by Cheapflights users on 6/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:30 amMCO - VQS
1 stop6h 05mJetBlue
Mon 12/158:45 amVQS - MCO
1 stop6h 07mJetBlue
Deal found 6/28$523
This Mytrip deal was found by Cheapflights users on 6/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/156:50 amMCO - VQS
3 stops25h 35mMultiple Airlines
Mon 7/214:20 pmVQS - MCO
2 stops24h 30mMultiple Airlines
Deal found 6/28$566
This United Airlines deal was found by Cheapflights users on 6/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:00 amMCO - CPX
2 stops10h 51mUnited Airlines
Mon 9/2910:13 amCPX - MCO
2 stops11h 28mUnited Airlines
Deal found 6/29$995

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 30, 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

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Wed 8/20

11:55 pm-2:44 am

Nonstop2h 49m

Aguadilla Borinquen

Tue 8/26

3:43 am-6:37 am

Nonstop2h 54m

$164

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Sat 9/27

11:40 pm-2:34 am

Nonstop2h 54m

San Juan Luis Munoz Marin Intl

Fri 10/3

1:11 am-6:03 pm

1 stop16h 52m

$168

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Mon 8/4

6:00 am-2:18 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Thu 8/7

10:14 pm-9:57 am

1 stop11h 43m

$169

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Tue 7/15

6:50 am-3:30 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Tue 7/22

2:40 am-5:47 am

Nonstop3h 07m

$171

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Fri 8/15

5:30 am-8:26 am

Nonstop2h 56m

Ponce Mercedita

Mon 8/18

9:16 am-12:27 pm

Nonstop3h 11m

$198

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Thu 8/7

11:20 am-2:10 pm

Nonstop2h 50m

Aguadilla Borinquen

Mon 8/11

3:16 pm-6:10 pm

Nonstop2h 54m

$232

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sat 7/26

5:05 am-8:02 am

Nonstop2h 57m

Ponce Mercedita

Mon 7/28

8:50 am-11:53 am

Nonstop3h 03m

$252

OrlandoMayagüez

MCO - MAZ

MCOMAZ

Orlando

Thu 7/24

6:00 am-1:27 pm

1 stop7h 27m

Mayagüez Eugenio M De Hostos

Mon 7/28

2:00 pm-7:50 pm

1 stop5h 50m

$461

OrlandoCulebra

MCO - CPX

MCOCPX

Orlando

Tue 9/23

6:15 am-12:11 pm

1 stop5h 56m

Culebra

Sun 9/28

3:05 pm-7:50 pm

1 stop4h 45m

$487

OrlandoVieques

MCO - VQS

MCOVQS

Orlando

Tue 7/15

6:50 am-8:25 am

3 stops25h 35m

Vieques

Mon 7/21

4:20 pm-4:50 pm

2 stops24h 30m

$566

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 23 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, September is the cheapest month in which you can book a flight from Kissimmee to Puerto Rico (average of $254). Flying from Kissimmee to Puerto Rico in June is currently the most expensive (average of $339). 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 June 30, 2025.

When flying from Kissimmee to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 29, 2025.

Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Friday afternoons 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 June 30, 2025.

The most flights from K1S to PR0 are scheduled on a Friday (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 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 June 30, 2025.
Read through reviews of airlines operating flights from Kissimmee to Puerto Rico, such as Southwest, United 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
4,278 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,852 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,920 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Spirit Airlines
6.3
Okay
8,096 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,289 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Kissimmee to Puerto Rico one-way?

    $95 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 $95 and $122, 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: JetBlue (85%), Azul (84%), Spirit Airlines (78%).

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

    On average you can expect to pay $223 for a flight from Kissimmee to Puerto Rico. The cheapest flight overall is $101 while the most popular route, (Orlando - San Juan Luis Munoz Marin Intl) is currently priced at $159.

  • 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, September is the cheapest month in which you can book a flight from Kissimmee to Puerto Rico (average of $254). Flying from Kissimmee to Puerto Rico in June is currently the most expensive (average of $339). 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.
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West Palm Beach to Luis Munoz Marin Intl flights
Tampa to Punta Cana flights
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Fort Lauderdale to Santiago de los Caballeros flights
West Palm Beach to Punta Cana flights
Tampa to Santo Domingo flights
Orlando to Castries flights
Tampa to Montego Bay flights
Miami to George Town flights
Fort Lauderdale to Oranjestad flights
Fort Lauderdale to Simpson Bay flights
Fort Lauderdale to Freeport flights
Fort Lauderdale to Aguadilla 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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$87Average$225FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$221FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$373FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$126Average$336FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$130Average$217FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$408FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$225Average$366FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$334Average$456FlexibilityNo cancel feeOn-time69%

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