$63+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Feb 24 — Mar 31
1 adult, Economy
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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 January 25, 2026.
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 January 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 2/2211:15 pm
MCO
- BQN
Nonstop2h 42m
Frontier
Fri 3/63:47 am
BQN
- MCO
Nonstop2h 59m
Frontier
Deal found 1/24![Frontier logo]()
$132
This CheapOair deal was found by Cheapflights users on 1/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:45 am
MCO
- PSE
Nonstop2h 51m
Frontier
Sun 5/1711:36 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 1/23![Frontier logo]()
$139
This Frontier deal was found by Cheapflights users on 1/25. 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 3/511:15 pm
MCO
- BQN
Nonstop2h 42m
Frontier
Mon 3/92:43 am
BQN
- MCO
Nonstop2h 59m
Frontier
Deal found 1/25![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 1/25. 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.
Fri 5/111:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Fri 5/82:38 am
BQN
- MCO
Nonstop3h 03m
Frontier
Deal found 1/25![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 4/1611:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Sun 4/192:38 am
BQN
- MCO
Nonstop3h 03m
Frontier
Deal found 1/24![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 3/106:30 am
MCO
- SJU
Nonstop2h 47m
Multiple Airlines
Tue 3/246:30 am
SJU
- MCO
Nonstop3h 30m
Multiple Airlines
Deal found 1/22![Multiple Airlines logo]()
$146
This Orbitz deal was found by Cheapflights users on 1/23. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1111:15 pm
MCO
- BQN
Nonstop2h 42m
Frontier
Sun 2/153:58 am
BQN
- MCO
Nonstop2h 59m
Frontier
Deal found 1/23![Frontier logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 1/23. 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 2/47:43 pm
MCO
- SJU
Nonstop2h 50m
Spirit Airlines
Sun 2/86:00 am
SJU
- MCO
Nonstop3h 15m
Spirit Airlines
Deal found 1/23![Spirit Airlines logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 1/23. 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.
Sat 2/286:30 am
MCO
- SJU
1 stop18h 55m
Frontier
Tue 3/35:25 pm
SJU
- MCO
Nonstop3h 29m
Frontier
Deal found 1/23![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Sat 2/79:00 am
MCO
- PSE
Nonstop2h 52m
Frontier
Sat 2/1411:35 am
PSE
- MCO
Nonstop3h 25m
Frontier
Deal found 1/23![Frontier logo]()
$148
This Frontier deal was found by Cheapflights users on 1/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2211:05 pm
MCO
- SJU
Nonstop2h 48m
Frontier
Tue 3/33:53 am
SJU
- MCO
Nonstop3h 12m
Frontier
Deal found 1/23![Frontier logo]()
$149
This Expedia deal was found by Cheapflights users on 1/24. 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.
Sat 2/216:00 am
MCO
- SJU
1 stop19h 25m
Multiple Airlines
Sat 2/288:05 pm
SJU
- MCO
Nonstop3h 20m
Multiple Airlines
Deal found 1/24![Multiple Airlines logo]()
$150
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 January 25, 2026.
Round-trip from | $132 (Kiwi.com) |
|---|---|
One-way from | $63 (Booking.com) |
Popular in | December |
Cheapest in | February |
Average price | $244 |
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 January 25, 2026.
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
Sat 2/7
9:00 am-12:52 pm
Nonstop2h 52m
Ponce Mercedita
Sat 2/14
11:35 am-2:00 pm
Nonstop3h 25m
$148
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Sat 2/28
9:54 am-1:46 pm
Nonstop2h 52m
Ponce Mercedita
Sat 3/7
12:25 pm-2:57 pm
Nonstop3h 32m
$166
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Mon 3/9
3:56 pm-10:37 am
1 stop18h 41m
San Juan Luis Munoz Marin Intl
Sat 3/14
1:45 am-5:00 am
Nonstop3h 15m
$177
OrlandoAguadilla
MCO - BQN
MCOBQN
Orlando
Fri 2/27
11:15 pm-2:57 am
Nonstop2h 42m
Aguadilla Borinquen
Sun 3/1
3:58 am-5:57 am
Nonstop2h 59m
$184
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Sat 1/31
9:00 am-12:52 pm
Nonstop2h 52m
Ponce Mercedita
Mon 2/9
4:10 pm-6:28 pm
Nonstop3h 18m
$189
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Mon 2/2
11:22 am-3:15 pm
Nonstop2h 53m
Ponce Mercedita
Fri 2/13
11:00 am-1:25 pm
Nonstop3h 25m
$192
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Sun 3/22
11:25 pm-2:13 am
Nonstop2h 48m
San Juan Luis Munoz Marin Intl
Mon 3/30
4:19 pm-12:35 am
1 stop8h 16m
$193
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Sat 1/31
5:15 pm-1:41 am
1 stop7h 26m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:59 am-5:41 pm
1 stop15h 42m
$197
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 4/3
4:10 pm-7:04 pm
Nonstop2h 54m
Ponce Mercedita
Sun 4/5
12:39 pm-4:02 pm
Nonstop3h 23m
$209
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Fri 1/30
11:27 am-3:26 pm
Nonstop2h 59m
San Juan Luis Munoz Marin Intl
Mon 2/2
11:15 am-1:35 pm
Nonstop3h 20m
$210
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 $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 January 25, 2026.
It’s optimal to fly from Kissimmee to Puerto Rico in the evening. By choosing this option you can save up to 26% 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 January 24, 2026.
Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Tuesday at noon 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 January 25, 2026.
The most flights from K1S to PR0 are scheduled on a Friday (19 on average). You will have fewer flight options on Sunday, 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 January 25, 2026.
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
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
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 7 airlines flying from Kissimmee to Puerto Rico
Discover the top 7 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 January 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$197 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$88 | Average$224 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$100 | Average$225 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$104 | Average$248 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$115 | Average$342 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$240 | Average$437 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$244 | Average$368 | FlexibilityNo cancel fee | On-time63% |