$81+ 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 11 — Jan 181
1 adult, Economy
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Kissimmee to Puerto Rico
Cheapest flights from Kissimmee to Puerto RicoExplore 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 12, 2025.
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 12, 2025.
This CheapOair deal was found by Cheapflights users on 12/10. 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.
Thu 12/117:30 amMCO - SJU
1 stop14h 55mSpirit Airlines
Sat 12/131:32 pmSJU - MCO
Nonstop3h 16mSpirit Airlines
Deal found 12/10![Spirit Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Thu 12/117:30 amMCO - SJU
1 stop14h 55mMultiple Airlines
Fri 12/123:55 amSJU - MCO
Nonstop3h 10mMultiple Airlines
Deal found 12/9![Multiple Airlines logo]()
$172
This Cheapflightsfares deal was found by Cheapflights users on 12/11. 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.
Tue 12/235:05 amMCO - SJU
1 stop19h 34mFrontier
Thu 1/159:04 pmSJU - MCO
Nonstop3h 22mFrontier
Deal found 12/11![Frontier logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 12/10. 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.
Tue 12/309:04 pmMCO - SJU
1 stop27h 20mFrontier
Mon 1/129:23 pmSJU - MCO
Nonstop3h 21mFrontier
Deal found 12/10![Frontier logo]()
$189
This Cheapflightsfares deal was found by Cheapflights users on 12/9. 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 12/297:34 pmMCO - SJU
1 stop15h 24mSpirit Airlines
Sat 1/108:05 pmSJU - MCO
Nonstop3h 20mSpirit Airlines
Deal found 12/9![Spirit Airlines logo]()
$190
This Frontier deal was found by Cheapflights users on 12/9. 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 12/1111:00 pmMCO - SJU
Nonstop2h 50mFrontier
Fri 12/123:55 amSJU - MCO
Nonstop3h 10mFrontier
Deal found 12/9![Frontier logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 12/11. 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.
Tue 12/235:05 amMCO - SJU
1 stop19h 34mFrontier
Fri 1/92:29 amSJU - MCO
1 stop11h 41mFrontier
Deal found 12/11![Frontier logo]()
$192
This CheapOair deal was found by Cheapflights users on 12/9. 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.
Mon 12/297:07 pmMCO - SJU
1 stop18h 50mFrontier
Fri 1/92:29 amSJU - MCO
1 stop8h 47mFrontier
Deal found 12/9![Frontier logo]()
$193
This Mytrip deal was found by Cheapflights users on 12/9. 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.
Thu 12/117:30 amMCO - SJU
1 stop14h 55mMultiple Airlines
Mon 12/1511:05 amSJU - MCO
Nonstop3h 22mMultiple Airlines
Deal found 12/9![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/305:15 amMCO - SJU
2 stops12h 58mMultiple Airlines
Fri 1/95:18 pmSJU - MCO
1 stop15h 25mMultiple Airlines
Deal found 12/10![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Sat 12/209:09 pmMCO - SJU
1 stop27h 15mFrontier
Mon 1/129:23 pmSJU - MCO
Nonstop3h 21mFrontier
Deal found 12/10![Frontier logo]()
$196
This CheapOair deal was found by Cheapflights users on 12/9. 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.
Tue 12/307:40 amMCO - PSE
Nonstop2h 54mFrontier
Mon 1/1912:14 pmPSE - MCO
Nonstop3h 32mFrontier
Deal found 12/9![Frontier logo]()
$199
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 12, 2025.
Round-trip from | $154 (Super.com) |
|---|---|
One-way from | $81 (Super.com) |
Popular in | December |
Cheapest in | February |
Average price | $347 |
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 12, 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 2/4
8:10 pm-11:59 pm
Nonstop2h 49m
San Juan Luis Munoz Marin Intl
Sun 2/8
6:00 am-8:30 am
Nonstop3h 30m
$171
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Sun 1/18
9:39 am-1:36 pm
Nonstop2h 57m
San Juan Luis Munoz Marin Intl
Thu 1/22
4:36 pm-7:05 pm
Nonstop3h 29m
$190
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 2/13
6:00 am-9:55 am
Nonstop2h 55m
Ponce Mercedita
Mon 2/16
10:50 am-1:14 pm
Nonstop3h 24m
$199
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Thu 1/8
7:18 am-4:13 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Mon 1/12
10:47 pm-3:33 pm
2 stops41h 46m
$204
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Wed 2/4
11:37 am-8:24 pm
1 stop7h 47m
San Juan Luis Munoz Marin Intl
Sun 2/8
7:44 pm-2:48 pm
1 stop20h 04m
$205
OrlandoAguadilla
MCO - BQN
MCOBQN
Orlando
Mon 1/5
4:05 pm-7:51 pm
Nonstop2h 46m
Aguadilla Borinquen
Thu 1/15
5:01 am-7:04 am
Nonstop3h 03m
$212
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 2/13
9:15 pm-1:08 am
Nonstop2h 53m
Ponce Mercedita
Fri 2/20
3:15 am-5:27 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
Sun 1/25
11:20 am-3:13 pm
Nonstop2h 53m
Ponce Mercedita
Thu 2/5
4:10 pm-6:28 pm
Nonstop3h 18m
$212
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Wed 2/18
9:15 pm-1:08 am
Nonstop2h 53m
Ponce Mercedita
Sun 2/22
3:15 am-5:27 am
Nonstop3h 12m
$212
Showing 1-10 of 60 results
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 $122). 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 12, 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 December 6, 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 12, 2025.
The most flights from K1S to PR0 are scheduled on a Thursday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 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 12, 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.
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Browse thousands of different options on Cheapflights for your next trip
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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.
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 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$197 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$92 | Average$227 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$109 | Average$233 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$114 | Average$251 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$134 | Average$374 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$438 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$244 | Average$366 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$325 | Average$504 | FlexibilityNo cancel fee | On-time69% |