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$73+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$154
(Trip.com)

One-way from

$73
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$187
From Kissimmee to Puerto Rico
Search Deals
One-way flight from Kissimmee to Puerto Rico
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Highest demand for flights based on searches. 14% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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.
Mon 8/115:23 pmMCO - SJU
Nonstop3h 09mFrontier
Thu 8/145:40 amSJU - MCO
Nonstop3h 05mFrontier
Deal found 4/23$146
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Sun 5/1111:12 amMCO - SJU
1 stop11h 05mMultiple Airlines
Fri 5/162:34 pmSJU - MCO
Nonstop3h 23mMultiple Airlines
Deal found 4/23$156
This eDestinos deal was found by Cheapflights users on 4/23. 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.
Sun 5/1111:12 amMCO - SJU
1 stop11h 05mSpirit Airlines
Thu 5/158:12 pmSJU - MCO
1 stop10h 55mSpirit Airlines
Deal found 4/23$162
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 5/2111:12 pmMCO - BQN
Nonstop2h 45mFrontier
Thu 5/292:59 amBQN - MCO
Nonstop3h 02mFrontier
Deal found 4/23$194
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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.
Sun 5/116:00 amMCO - PSE
Nonstop2h 56mFrontier
Thu 5/159:46 amPSE - MCO
Nonstop3h 18mFrontier
Deal found 4/23$224
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Wed 5/219:55 pmMCO - BQN
Nonstop2h 48mJetBlue
Wed 5/2811:40 amBQN - MCO
Nonstop2h 58mJetBlue
Deal found 4/23$246
This JetBlue deal was found by Cheapflights users on 4/23. 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 5/88:59 pmMCO - PSE
Nonstop3h 00mJetBlue
Sun 5/115:09 amPSE - MCO
Nonstop3h 11mJetBlue
Deal found 4/23$256
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/87:00 amMCO - SJU
1 stop9h 33mDelta
Thu 5/152:31 pmSJU - MCO
1 stop9h 53mDelta
Deal found 4/23$273
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Wed 5/218:25 pmMCO - SJU
Nonstop3h 00mJetBlue
Tue 5/273:33 amSJU - MCO
1 stop10h 06mJetBlue
Deal found 4/23$298
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 5/712:36 pmMCO - BQN
1 stop10h 33mUnited Airlines
Mon 5/1212:15 amBQN - MCO
1 stop8h 34mUnited Airlines
Deal found 4/23$415
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Fri 5/96:15 amMCO - MAZ
1 stop6h 37mJetBlue
Tue 5/134:13 pmMAZ - MCO
1 stop8h 37mJetBlue
Deal found 4/23$484
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Wed 5/78:40 amMCO - CPX
1 stop4h 59mJetBlue
Tue 5/135:41 pmCPX - MCO
1 stop7h 09mJetBlue
Deal found 4/23$497

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 April 24, 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

Tue 5/13

11:59 pm-2:51 am

Nonstop2h 52m

San Juan Luis Munoz Marin Intl

Fri 5/16

9:30 pm-12:43 am

Nonstop3h 13m

$154

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Sun 5/11

11:12 am-10:17 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Fri 5/16

2:34 pm-5:57 pm

Nonstop3h 23m

$156

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Sun 5/11

11:12 am-10:17 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Thu 5/15

8:12 pm-7:07 am

1 stop10h 55m

$162

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Wed 5/21

11:12 pm-1:57 am

Nonstop2h 45m

Aguadilla Borinquen

Thu 5/29

2:59 am-6:01 am

Nonstop3h 02m

$194

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Sun 5/11

6:00 am-8:56 am

Nonstop2h 56m

Ponce Mercedita

Thu 5/15

9:46 am-1:04 pm

Nonstop3h 18m

$224

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Wed 5/21

9:55 pm-12:43 am

Nonstop2h 48m

Aguadilla Borinquen

Wed 5/28

11:40 am-2:38 pm

Nonstop2h 58m

$246

OrlandoPonce

MCO - PSE

MCOPSE

Orlando

Thu 5/8

8:59 pm-11:59 pm

Nonstop3h 00m

Ponce Mercedita

Sun 5/11

5:09 am-8:20 am

Nonstop3h 11m

$256

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Thu 5/8

7:00 am-4:33 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Thu 5/15

2:31 pm-12:24 am

1 stop9h 53m

$273

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Wed 5/21

8:25 pm-11:25 pm

Nonstop3h 00m

San Juan Luis Munoz Marin Intl

Tue 5/27

3:33 am-1:39 pm

1 stop10h 06m

$298

OrlandoAguadilla

MCO - BQN

MCOBQN

Orlando

Wed 5/7

12:36 pm-11:09 pm

1 stop10h 33m

Aguadilla Borinquen

Mon 5/12

12:15 am-8:49 am

1 stop8h 34m

$415

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 33 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 December is currently the most expensive (average of $336). 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 April 24, 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 March 30, 2025.

Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Friday at noon 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 April 24, 2025.

The most flights from K1S to PR0 are scheduled on a Tuesday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 24, 2025.
Read through reviews of airlines operating flights from Kissimmee to Puerto Rico, such as Southwest, Delta and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $73 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 $76 and $133, 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 (91%), JetBlue (81%), Southwest (80%).

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

    On average you can expect to pay $200 for a flight from Kissimmee to Puerto Rico. The cheapest flight overall is $80 while the most popular route, (Orlando - San Juan Luis Munoz Marin Intl) is currently priced at $148.

  • 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 December is currently the most expensive (average of $336). 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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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$49Average$196FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$87Average$186FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$126Average$301FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$130Average$191FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$202Average$503FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$216Average$418FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$358FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$324Average$471FlexibilityNo cancel feeOn-time69%

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