$100+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Sep 2 — Sep 91
Round-trip
1 adult, Economy
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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
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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 August 3, 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 August 3, 2026.
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Sat 8/223:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 7/30![Frontier logo]()
$184
This Super.com deal was found by Cheapflights users on 8/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Sun 8/233:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 8/1![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 8/1. 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 8/1911:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Tue 8/253:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 8/1![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:15 am
MCO
- BQN
Nonstop2h 54m
Frontier
Sun 9/2011:08 am
BQN
- MCO
Nonstop2h 56m
Frontier
Deal found 7/30![Frontier logo]()
$189
This Super.com deal was found by Cheapflights users on 8/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Thu 8/273:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 8/1![Frontier logo]()
$190
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:19 am
MCO
- BQN
Nonstop2h 54m
Frontier
Sun 10/411:08 am
BQN
- MCO
Nonstop2h 56m
Frontier
Deal found 7/30![Frontier logo]()
$194
This Frontier deal was found by Cheapflights users on 7/31. 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.
Mon 8/175:01 am
MCO
- SJU
Nonstop2h 56m
Frontier
Tue 8/256:09 pm
SJU
- MCO
Nonstop3h 12m
Frontier
Deal found 7/31![Frontier logo]()
$194
This Super.com deal was found by Cheapflights users on 8/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 am
MCO
- BQN
Nonstop2h 54m
Frontier
Tue 9/2210:52 am
BQN
- MCO
Nonstop2h 56m
Frontier
Deal found 8/2![Frontier logo]()
$195
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:45 pm
MCO
- SJU
Nonstop3h 07m
Frontier
Sat 9/512:11 pm
SJU
- MCO
Nonstop3h 14m
Frontier
Deal found 7/30![Frontier logo]()
$195
This Super.com deal was found by Cheapflights users on 8/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:19 am
MCO
- BQN
Nonstop2h 54m
Frontier
Fri 9/2511:08 am
BQN
- MCO
Nonstop2h 56m
Frontier
Deal found 8/1![Frontier logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 7/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:44 pm
MCO
- SJU
Nonstop3h 05m
Frontier
Fri 8/283:10 am
SJU
- MCO
Nonstop3h 00m
Frontier
Deal found 7/30![Frontier logo]()
$196
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Sun 8/233:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 7/30![Frontier logo]()
$197
Best flights from Kissimmee to Puerto RicoDiscover carefully curated flight deals from Kissimmee to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 3, 2026.
Discover carefully curated flight deals from Kissimmee to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 3, 2026.
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:45 pm
MCO
- SJU
2 stops10h 10m
Southwest
Sun 9/2710:05 am
SJU
- MCO
Nonstop3h 00m
Southwest
Deal found 7/31![Southwest logo]()
$252
This Super.com deal was found by Cheapflights users on 8/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:00 am
MCO
- PSE
Nonstop3h 02m
Frontier
Sun 8/2310:47 am
PSE
- MCO
Nonstop3h 07m
Frontier
Deal found 8/2![Frontier logo]()
$263
This JetBlue deal was found by Cheapflights users on 7/31. 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 9/125:05 am
MCO
- PSE
Nonstop2h 56m
JetBlue
Wed 9/168:55 am
PSE
- MCO
Nonstop3h 06m
JetBlue
Deal found 7/31![JetBlue logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Fri 8/2111:17 pm
MCO
- MAZ
1 stop10h 25m
Multiple Airlines
Mon 8/241:19 pm
MAZ
- MCO
1 stop8h 02m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$340
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/102:20 pm
MCO
- BQN
1 stop8h 49m
United Airlines
Sun 9/1312:15 am
BQN
- MCO
1 stop9h 06m
United Airlines
Deal found 7/31![United Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:20 am
MCO
- SJU
2 stops11h 40m
Southwest
Thu 9/35:30 am
SJU
- MCO
2 stops10h 50m
Southwest
Deal found 7/29![Southwest logo]()
$256
This JetBlue deal was found by Cheapflights users on 7/31. 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 8/156:24 pm
MCO
- PSE
1 stop5h 35m
JetBlue
Wed 8/198:48 am
PSE
- MCO
Nonstop3h 03m
JetBlue
Deal found 7/31![JetBlue logo]()
$278
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:40 am
MCO
- SJU
2 stops10h 20m
Southwest
Wed 9/96:00 am
SJU
- MCO
2 stops13h 20m
Southwest
Deal found 7/30![Southwest logo]()
$265
This JetBlue deal was found by Cheapflights users on 7/30. 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 8/276:24 pm
MCO
- PSE
1 stop5h 35m
JetBlue
Sun 8/305:01 am
PSE
- MCO
1 stop6h 01m
JetBlue
Deal found 7/30![JetBlue logo]()
$282
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:05 pm
MCO
- SJU
1 stop8h 50m
Southwest
Tue 9/226:00 am
SJU
- MCO
2 stops13h 20m
Southwest
Deal found 7/31![Southwest logo]()
$267
This JetBlue deal was found by Cheapflights users on 7/30. 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.
Fri 8/146:24 pm
MCO
- PSE
1 stop5h 35m
JetBlue
Mon 8/175:01 am
PSE
- MCO
1 stop6h 01m
JetBlue
Deal found 7/30![JetBlue logo]()
$282
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:40 am
MCO
- PSE
Nonstop3h 01m
Frontier
Sun 8/910:06 am
PSE
- MCO
Nonstop3h 07m
Frontier
Deal found 7/29![Frontier logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:17 pm
MCO
- MAZ
1 stop10h 25m
Multiple Airlines
Mon 8/171:19 pm
MAZ
- MCO
1 stop12h 38m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:45 pm
MCO
- SJU
2 stops10h 20m
Southwest
Mon 11/22:20 pm
SJU
- MCO
1 stop5h 30m
Southwest
Deal found 7/29![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:45 pm
MCO
- SJU
1 stop10h 05m
Southwest
Sat 9/55:55 am
SJU
- MCO
2 stops11h 00m
Southwest
Deal found 7/29![Southwest logo]()
$272
This JetBlue deal was found by Cheapflights users on 7/29. 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.
Wed 8/193:05 pm
MCO
- BQN
Nonstop2h 58m
JetBlue
Mon 8/248:39 am
BQN
- MCO
Nonstop2h 54m
JetBlue
Deal found 7/29![JetBlue logo]()
$301
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:30 pm
MCO
- SJU
2 stops9h 35m
Southwest
Sun 10/115:30 am
SJU
- MCO
1 stop7h 55m
Southwest
Deal found 7/31![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 8/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:45 am
MCO
- SJU
1 stop9h 15m
Southwest
Mon 10/55:30 am
SJU
- MCO
2 stops9h 45m
Southwest
Deal found 8/2![Southwest logo]()
$278
This JetBlue deal was found by Cheapflights users on 7/29. 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 8/255:01 am
MCO
- BQN
Nonstop2h 48m
JetBlue
Sat 8/292:30 pm
BQN
- MCO
1 stop7h 46m
JetBlue
Deal found 7/29![JetBlue logo]()
$340
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/172:20 pm
MCO
- BQN
1 stop8h 49m
United Airlines
Sat 9/1912:15 am
BQN
- MCO
1 stop9h 06m
United Airlines
Deal found 7/31![United Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/2011:16 am
MCO
- CPX
1 stop6h 05m
Multiple Airlines
Wed 9/233:05 pm
CPX
- MCO
1 stop6h 47m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 8/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:45 pm
MCO
- SJU
2 stops10h 10m
Southwest
Tue 9/296:00 am
SJU
- MCO
2 stops12h 30m
Southwest
Deal found 8/2![Southwest logo]()
$278
This JetBlue deal was found by Cheapflights users on 7/30. 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.
Sat 9/55:01 am
MCO
- PSE
Nonstop2h 57m
JetBlue
Sun 9/68:48 am
PSE
- MCO
Nonstop3h 03m
JetBlue
Deal found 7/30![JetBlue logo]()
$353
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Thu 10/11:48 pm
MCO
- BQN
1 stop9h 21m
United Airlines
Sat 10/312:15 am
BQN
- MCO
1 stop9h 06m
United Airlines
Deal found 8/2![United Airlines logo]()
$532
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/232:25 pm
MCO
- SJU
2 stops9h 25m
Southwest
Wed 8/266:00 am
SJU
- MCO
1 stop8h 45m
Southwest
Deal found 8/1![Southwest logo]()
$278
This JetBlue deal was found by Cheapflights users on 7/29. 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.
Fri 9/45:01 am
MCO
- PSE
Nonstop2h 57m
JetBlue
Tue 9/88:48 am
PSE
- MCO
Nonstop3h 03m
JetBlue
Deal found 7/29![JetBlue logo]()
$355
This JetBlue deal was found by Cheapflights users on 8/2. 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 8/215:01 am
MCO
- PSE
Nonstop2h 57m
JetBlue
Tue 8/258:48 am
PSE
- MCO
Nonstop3h 03m
JetBlue
Deal found 8/2![JetBlue logo]()
$368
This Travelocity deal was found by Cheapflights users on 8/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:04 am
MCO
- VQS
1 stop7h 21m
Multiple Airlines
Sun 9/131:51 pm
VQS
- MCO
1 stop8h 01m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$608
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/152:20 pm
MCO
- BQN
1 stop8h 49m
United Airlines
Tue 9/2212:15 am
BQN
- MCO
2 stops19h 43m
United Airlines
Deal found 7/31![United Airlines logo]()
$623
This JetBlue deal was found by Cheapflights users on 7/30. 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.
Sat 9/55:01 am
MCO
- PSE
Nonstop2h 57m
JetBlue
Mon 9/78:48 am
PSE
- MCO
Nonstop3h 03m
JetBlue
Deal found 7/30![JetBlue logo]()
$368
Last-minute flights from Kissimmee to Puerto RicoDiscover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated August 3, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated August 3, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/31. 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.
Mon 8/175:01 am
MCO
- SJU
Nonstop2h 56m
Frontier
Tue 8/256:09 pm
SJU
- MCO
Nonstop3h 12m
Frontier
Deal found 7/31![Frontier logo]()
$194
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Thu 8/203:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 7/30![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Sat 8/223:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 7/30![Frontier logo]()
$184
This Super.com deal was found by Cheapflights users on 8/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Sun 8/233:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 8/1![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 8/1. 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 8/1911:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Tue 8/253:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 8/1![Frontier logo]()
$188
This Super.com deal was found by Cheapflights users on 8/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Thu 8/273:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 8/1![Frontier logo]()
$190
This Super.com deal was found by Cheapflights users on 7/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:24 pm
MCO
- SJU
1 stop4h 56m
JetBlue
Sun 8/235:05 am
SJU
- MCO
1 stop5h 57m
JetBlue
Deal found 7/29![JetBlue logo]()
$197
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Sun 8/233:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 7/30![Frontier logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 7/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:44 pm
MCO
- SJU
Nonstop3h 05m
Frontier
Fri 8/283:10 am
SJU
- MCO
Nonstop3h 00m
Frontier
Deal found 7/30![Frontier logo]()
$196
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:15 am
MCO
- BQN
Nonstop2h 54m
Frontier
Sun 9/2011:08 am
BQN
- MCO
Nonstop2h 56m
Frontier
Deal found 7/30![Frontier logo]()
$189
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Sat 8/293:10 am
BQN
- MCO
Nonstop2h 51m
Frontier
Deal found 7/29![Frontier logo]()
$194
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:45 pm
MCO
- SJU
Nonstop3h 07m
Frontier
Sat 9/512:11 pm
SJU
- MCO
Nonstop3h 14m
Frontier
Deal found 7/30![Frontier logo]()
$195
One-way flights from Kissimmee to Puerto RicoSearch for one-way flight options from Kissimmee to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
Search for one-way flight options from Kissimmee to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
This Super.com deal was found by Cheapflights users on 7/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:24 pm
MCO
- SJU
1 stop4h 56m
JetBlue
Deal found 7/30![JetBlue logo]()
$100
This Super.com deal was found by Cheapflights users on 7/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:24 pm
MCO
- SJU
1 stop4h 56m
JetBlue
Deal found 7/29![JetBlue logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/811:17 pm
MCO
- SJU
Nonstop2h 58m
Frontier
Deal found 8/2![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 8/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:24 pm
MCO
- SJU
1 stop4h 56m
JetBlue
Deal found 8/3![JetBlue logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:40 am
MCO
- SJU
Nonstop3h 03m
Frontier
Deal found 7/29![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 7/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:17 pm
MCO
- SJU
Nonstop2h 58m
Frontier
Deal found 7/30![Frontier logo]()
$106
This Frontier deal was found by Cheapflights users on 7/31. 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.
Mon 8/3111:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Deal found 7/31![Frontier logo]()
$107
This eDestinos deal was found by Cheapflights users on 8/2. 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 9/111:04 am
MCO
- SJU
1 stop15h 55m
Frontier
Deal found 8/2![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Deal found 7/30![Frontier logo]()
$108
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
MCO
- SJU
1 stop12h 33m
American Airlines
Deal found 7/30![American Airlines logo]()
$108
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1411:17 pm
MCO
- BQN
Nonstop2h 53m
Frontier
Deal found 7/30![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:24 pm
MCO
- SJU
1 stop4h 56m
JetBlue
Deal found 7/31![JetBlue logo]()
$109
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 August 3, 2026.
Round-trip from | $184 (Frontier) |
|---|---|
One-way from | $100 (Super.com) |
Popular in | December |
Cheapest in | February |
Average price | $275 |
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 August 3, 2026.
Use the filters below to find and compare flights from Kissimmee to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Thu 9/24
12:45 pm-10:55 pm
2 stops10h 10m
San Juan Luis Munoz Marin Intl
Sun 9/27
10:05 am-1:05 pm
Nonstop3h 00m
$252
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Tue 9/1
10:20 am-10:00 pm
2 stops11h 40m
San Juan Luis Munoz Marin Intl
Thu 9/3
5:30 am-4:20 pm
2 stops10h 50m
$256
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 8/21
7:00 am-10:02 am
Nonstop3h 02m
Ponce Mercedita
Sun 8/23
10:47 am-1:54 pm
Nonstop3h 07m
$263
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Wed 8/26
8:40 am-7:00 pm
2 stops10h 20m
San Juan Luis Munoz Marin Intl
Wed 9/9
6:00 am-7:20 pm
2 stops13h 20m
$265
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Thu 9/17
2:05 pm-10:55 pm
1 stop8h 50m
San Juan Luis Munoz Marin Intl
Tue 9/22
6:00 am-7:20 pm
2 stops13h 20m
$267
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Thu 10/29
12:45 pm-11:05 pm
2 stops10h 20m
San Juan Luis Munoz Marin Intl
Mon 11/2
2:20 pm-6:50 pm
1 stop5h 30m
$272
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Fri 8/28
12:45 pm-10:50 pm
1 stop10h 05m
San Juan Luis Munoz Marin Intl
Sat 9/5
5:55 am-4:55 pm
2 stops11h 00m
$272
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Sat 9/12
5:05 am-8:01 am
Nonstop2h 56m
Ponce Mercedita
Wed 9/16
8:55 am-12:01 pm
Nonstop3h 06m
$273
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Sat 8/15
6:24 pm-11:59 pm
1 stop5h 35m
Ponce Mercedita
Wed 8/19
8:48 am-11:51 am
Nonstop3h 03m
$278
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Thu 10/1
2:30 pm-12:05 am
2 stops9h 35m
San Juan Luis Munoz Marin Intl
Sun 10/11
5:30 am-1:25 pm
1 stop7h 55m
$278
Showing 1-10 of 60 resultsSorted by cheapest first
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.
MCO-BQN
MCO-SJU
MCO-PSE
MCO-MAZ
MCO-CPX
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
K1S-PR0
MCO-BQN
MCO-SJU
MCO-PSE
MCO-MAZ
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 August 3, 2026.
It’s optimal to fly from Kissimmee to Puerto Rico in the evening. By choosing this option you can save up to 18% on the cost of your flight, compared to a flight in the afternoon.
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 August 3, 2026.
The most flights from K1S to PR0 are scheduled on a Sunday (30 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 on average).
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 August 1, 2026.
Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Sunday afternoons when fares are most often at their lowest. Tuesday 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 August 3, 2026.
Read through reviews of airlines operating flights from Kissimmee to Puerto Rico, such as Southwest,Delta, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your 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.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kissimmee to Puerto Rico by cabin class
Find flights from Kissimmee to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kissimmee and Puerto Rico flights
Browse other Kissimmee and Puerto Rico flight options. Last updated on August 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Kissimmee to Puerto Rico
Discover the top 6 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 August 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$222 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$113 | Average$285 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$153 | Average$368 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$226 | Average$373 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$366 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$253 | Average$329 | FlexibilityNo cancel fee | On-timeN/A |