$89+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
May 22 — May 291
Round-trip
1 adult, Economy
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Find cheap flights from Kissimmee to Puerto Rico with Cheapflights
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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 April 22, 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 April 22, 2026.
This eDestinos deal was found by Cheapflights users on 4/17. 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.
Fri 5/86:15 am
MCO
- SJU
1 stop18h 06m
Frontier
Fri 5/157:20 am
SJU
- MCO
1 stop14h 33m
Frontier
Deal found 4/17![Frontier logo]()
$168
This eDestinos deal was found by Cheapflights users on 4/20. 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.
Sat 4/252:29 pm
MCO
- SJU
1 stop10h 25m
Spirit Airlines
Fri 5/12:09 am
SJU
- MCO
1 stop11h 15m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 5/136:20 am
MCO
- SJU
1 stop17h 39m
Frontier
Sat 5/166:30 am
SJU
- MCO
1 stop17h 14m
Frontier
Deal found 4/21![Frontier logo]()
$175
This eDestinos deal was found by Cheapflights users on 4/21. 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.
Sat 5/96:15 am
MCO
- SJU
1 stop17h 44m
Frontier
Wed 5/135:15 pm
SJU
- MCO
1 stop13h 25m
Frontier
Deal found 4/21![Frontier logo]()
$178
This eDestinos deal was found by Cheapflights users on 4/18. 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.
Sat 5/236:15 am
MCO
- SJU
1 stop21h 46m
Frontier
Sat 5/308:32 am
SJU
- MCO
1 stop13h 21m
Frontier
Deal found 4/18![Frontier logo]()
$180
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:00 am
MCO
- SJU
1 stop17h 54m
Multiple Airlines
Sat 5/166:30 am
SJU
- MCO
1 stop17h 14m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$182
This eDestinos deal was found by Cheapflights users on 4/20. 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.
Sat 5/306:15 am
MCO
- SJU
1 stop21h 46m
Frontier
Sat 6/65:15 pm
SJU
- MCO
1 stop13h 25m
Frontier
Deal found 4/20![Frontier logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 5/76:15 am
MCO
- SJU
1 stop21h 46m
Frontier
Sun 5/103:12 pm
SJU
- MCO
1 stop8h 32m
Frontier
Deal found 4/17![Frontier logo]()
$185
This Super.com deal was found by Cheapflights users on 4/21. 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 8/1511:12 pm
MCO
- BQN
Nonstop2h 52m
Frontier
Tue 8/182:59 am
BQN
- MCO
Nonstop2h 53m
Frontier
Deal found 4/21![Frontier logo]()
$192
This CheapOair deal was found by Cheapflights users on 4/19. 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 5/1911:17 pm
MCO
- BQN
Nonstop2h 45m
Frontier
Wed 5/202:59 am
BQN
- MCO
Nonstop2h 58m
Frontier
Deal found 4/19![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 8/2511:12 pm
MCO
- BQN
Nonstop2h 52m
Frontier
Fri 8/282:59 am
BQN
- MCO
Nonstop2h 53m
Frontier
Deal found 4/22![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/511:17 pm
MCO
- BQN
Nonstop2h 45m
Frontier
Mon 5/112:59 am
BQN
- MCO
Nonstop2h 58m
Frontier
Deal found 4/22![Frontier logo]()
$202
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 April 22, 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 April 22, 2026.
This Super.com deal was found by Cheapflights users on 4/18. 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 5/116:05 am
MCO
- PSE
Nonstop2h 57m
Frontier
Fri 5/159:47 am
PSE
- MCO
Nonstop3h 15m
Frontier
Deal found 4/18![Frontier logo]()
$223
This Delta deal was found by Cheapflights users on 4/17. 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.
Wed 7/157:00 am
MCO
- SJU
1 stop9h 45m
Delta
Sat 7/182:42 pm
SJU
- MCO
1 stop9h 33m
Delta
Deal found 4/17![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 4/18. 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 6/96:05 am
MCO
- SJU
Nonstop2h 55m
Southwest
Tue 6/97:20 pm
SJU
- MCO
Nonstop3h 00m
Southwest
Deal found 4/18![Southwest logo]()
$358
This Mytrip deal was found by Cheapflights users on 4/20. 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 5/59:24 pm
MCO
- MAZ
1 stop12h 18m
Multiple Airlines
Sat 5/94:36 pm
MAZ
- MCO
1 stop13h 26m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$382
This JetBlue deal was found by Cheapflights users on 4/19. 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 6/44:00 pm
MCO
- BQN
1 stop10h 57m
JetBlue
Wed 6/105:01 am
BQN
- MCO
Nonstop2h 59m
JetBlue
Deal found 4/19![JetBlue logo]()
$440
This Frontier deal was found by Cheapflights users on 4/19. 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 5/146:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Tue 5/1910:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/19![Frontier logo]()
$224
This Frontier deal was found by Cheapflights users on 4/19. 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.
Sat 5/96:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Sun 5/1010:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/19![Frontier logo]()
$226
This United Airlines deal was found by Cheapflights users on 4/17. 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 4/281:19 pm
MCO
- BQN
1 stop9h 50m
United Airlines
Sat 5/212:15 am
BQN
- MCO
1 stop10h 43m
United Airlines
Deal found 4/17![United Airlines logo]()
$519
This Frontier deal was found by Cheapflights users on 4/19. 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 5/86:05 am
MCO
- PSE
Nonstop2h 57m
Frontier
Sun 5/1010:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/19![Frontier logo]()
$232
This CheapOair deal was found by Cheapflights users on 4/17. 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.
Sat 6/136:45 am
MCO
- PSE
Nonstop2h 57m
Frontier
Tue 6/1610:27 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/17![Frontier logo]()
$242
This Delta deal was found by Cheapflights users on 4/17. 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.
Wed 7/157:00 am
MCO
- SJU
1 stop9h 45m
Delta
Thu 7/232:42 pm
SJU
- MCO
1 stop10h 19m
Delta
Deal found 4/17![Delta logo]()
$354
This Frontier deal was found by Cheapflights users on 4/18. 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 5/67:30 am
MCO
- PSE
Nonstop2h 58m
Frontier
Sat 5/910:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/18![Frontier logo]()
$244
This Southwest deal was found by Cheapflights users on 4/19. 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 5/79:05 pm
MCO
- SJU
Nonstop2h 50m
Southwest
Sun 5/109:45 pm
SJU
- MCO
Nonstop3h 10m
Southwest
Deal found 4/19![Southwest logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Thu 5/79:04 am
MCO
- MAZ
2 stops31h 07m
Multiple Airlines
Mon 5/111:19 pm
MAZ
- MCO
1 stop16h 43m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/33:20 pm
MCO
- SJU
2 stops8h 55m
Southwest
Thu 7/97:00 am
SJU
- MCO
2 stops13h 00m
Southwest
Deal found 4/22![Southwest logo]()
$378
This Delta deal was found by Cheapflights users on 4/17. 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.
Wed 4/299:00 am
MCO
- SJU
1 stop7h 23m
Delta
Tue 5/126:15 am
SJU
- MCO
1 stop9h 53m
Delta
Deal found 4/17![Delta logo]()
$383
This CheapOair deal was found by Cheapflights users on 4/17. 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 5/156:05 am
MCO
- PSE
Nonstop2h 57m
Frontier
Mon 5/189:47 am
PSE
- MCO
Nonstop3h 15m
Frontier
Deal found 4/17![Frontier logo]()
$279
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 5/910:05 am
MCO
- SJU
Nonstop2h 50m
Southwest
Mon 5/115:05 am
SJU
- MCO
Nonstop3h 15m
Southwest
Deal found 4/21![Southwest logo]()
$381
This Delta deal was found by Cheapflights users on 4/17. 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.
Sun 7/195:30 am
MCO
- SJU
1 stop6h 16m
Delta
Thu 7/232:42 pm
SJU
- MCO
1 stop10h 19m
Delta
Deal found 4/17![Delta logo]()
$424
This Frontier deal was found by Cheapflights users on 4/21. 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 5/86:05 am
MCO
- PSE
Nonstop2h 57m
Frontier
Mon 5/119:47 am
PSE
- MCO
Nonstop3h 15m
Frontier
Deal found 4/21![Frontier logo]()
$290
This Southwest deal was found by Cheapflights users on 4/19. 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 5/82:00 pm
MCO
- SJU
2 stops9h 40m
Southwest
Wed 5/135:05 am
SJU
- MCO
2 stops9h 55m
Southwest
Deal found 4/19![Southwest logo]()
$392
This JetBlue deal was found by Cheapflights users on 4/20. 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 5/65:01 am
MCO
- MAZ
1 stop4h 41m
JetBlue
Sun 5/104:36 pm
MAZ
- MCO
1 stop8h 23m
JetBlue
Deal found 4/20![JetBlue logo]()
$528
This United Airlines deal was found by Cheapflights users on 4/18. 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 4/301:16 pm
MCO
- BQN
1 stop9h 53m
United Airlines
Sat 5/212:15 am
BQN
- MCO
1 stop10h 43m
United Airlines
Deal found 4/18![United Airlines logo]()
$555
This CheapOair deal was found by Cheapflights users on 4/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Mon 5/189:47 am
PSE
- MCO
Nonstop3h 15m
Frontier
Deal found 4/22![Frontier logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Mon 5/411:10 pm
MCO
- VQS
1 stop12h 14m
Multiple Airlines
Sat 5/94:13 pm
VQS
- MCO
2 stops31h 31m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$564
This JetBlue deal was found by Cheapflights users on 4/17. 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 4/308:00 am
MCO
- MAZ
1 stop4h 44m
JetBlue
Sun 5/34:36 pm
MAZ
- MCO
1 stop8h 23m
JetBlue
Deal found 4/17![JetBlue logo]()
$568
This United Airlines deal was found by Cheapflights users on 4/17. 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 6/112:05 pm
MCO
- BQN
1 stop9h 04m
United Airlines
Mon 6/1512:15 am
BQN
- MCO
1 stop9h 01m
United Airlines
Deal found 4/17![United Airlines logo]()
$573
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/163:20 pm
MCO
- SJU
2 stops8h 55m
Southwest
Thu 7/237:00 am
SJU
- MCO
2 stops13h 00m
Southwest
Deal found 4/22![Southwest logo]()
$443
This KAYAK deal was found by Cheapflights users on 4/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:55 am
MCO
- MAZ
1 stop6h 49m
JetBlue
Sat 7/181:19 pm
MAZ
- MCO
1 stop6h 46m
JetBlue
Deal found 4/21![JetBlue logo]()
$586
This Southwest deal was found by Cheapflights users on 4/20. 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.
Mon 7/203:20 pm
MCO
- SJU
2 stops8h 55m
Southwest
Mon 8/35:15 pm
SJU
- MCO
1 stop7h 30m
Southwest
Deal found 4/20![Southwest logo]()
$443
Last-minute flights from Kissimmee to Puerto RicoDiscover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated April 22, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated April 22, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 4/20. 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.
Sat 4/252:29 pm
MCO
- SJU
1 stop10h 25m
Spirit Airlines
Fri 5/12:09 am
SJU
- MCO
1 stop11h 15m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$170
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:00 am
MCO
- SJU
1 stop17h 54m
Multiple Airlines
Sat 5/166:30 am
SJU
- MCO
1 stop17h 14m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/511:17 pm
MCO
- BQN
Nonstop2h 45m
Frontier
Mon 5/112:59 am
BQN
- MCO
Nonstop2h 58m
Frontier
Deal found 4/22![Frontier logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 5/76:15 am
MCO
- SJU
1 stop21h 46m
Frontier
Sun 5/103:12 pm
SJU
- MCO
1 stop8h 32m
Frontier
Deal found 4/17![Frontier logo]()
$185
This eDestinos deal was found by Cheapflights users on 4/17. 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.
Fri 5/86:15 am
MCO
- SJU
1 stop18h 06m
Frontier
Fri 5/157:20 am
SJU
- MCO
1 stop14h 33m
Frontier
Deal found 4/17![Frontier logo]()
$168
This eDestinos deal was found by Cheapflights users on 4/21. 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.
Sat 5/96:15 am
MCO
- SJU
1 stop17h 44m
Frontier
Wed 5/135:15 pm
SJU
- MCO
1 stop13h 25m
Frontier
Deal found 4/21![Frontier logo]()
$178
This Orbitz deal was found by Cheapflights users on 4/17. 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.
Sat 5/96:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Mon 5/119:47 am
PSE
- MCO
Nonstop3h 15m
Frontier
Deal found 4/17![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 4/19. 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 5/126:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Thu 5/1410:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/19![Frontier logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 5/136:20 am
MCO
- SJU
1 stop17h 39m
Frontier
Sat 5/166:30 am
SJU
- MCO
1 stop17h 14m
Frontier
Deal found 4/21![Frontier logo]()
$175
This CheapOair deal was found by Cheapflights users on 4/19. 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 5/1911:17 pm
MCO
- BQN
Nonstop2h 45m
Frontier
Wed 5/202:59 am
BQN
- MCO
Nonstop2h 58m
Frontier
Deal found 4/19![Frontier logo]()
$194
This eDestinos deal was found by Cheapflights users on 4/18. 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.
Sat 5/236:15 am
MCO
- SJU
1 stop21h 46m
Frontier
Fri 5/298:32 am
SJU
- MCO
1 stop13h 21m
Frontier
Deal found 4/18![Frontier logo]()
$180
This eDestinos deal was found by Cheapflights users on 4/20. 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.
Sat 5/306:15 am
MCO
- SJU
1 stop21h 46m
Frontier
Sat 6/65:15 pm
SJU
- MCO
1 stop13h 25m
Frontier
Deal found 4/20![Frontier logo]()
$183
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 April 22, 2026.
Search for one-way flight options from Kissimmee to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
This eDestinos deal was found by Cheapflights users on 4/19. 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.
Thu 5/79:04 am
MCO
- SJU
1 stop15h 17m
Frontier
Deal found 4/19![Frontier logo]()
$89
This eDestinos deal was found by Cheapflights users on 4/17. 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.
Sat 5/304:40 pm
MCO
- SJU
1 stop11h 21m
Frontier
Deal found 4/17![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 4/20. 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 5/146:15 am
MCO
- SJU
1 stop21h 46m
Frontier
Deal found 4/20![Frontier logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 4/252:29 pm
MCO
- SJU
1 stop10h 25m
Spirit Airlines
Deal found 4/21![Spirit Airlines logo]()
$94
This Super.com deal was found by Cheapflights users on 4/21. 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 5/1211:17 pm
MCO
- BQN
Nonstop2h 45m
Frontier
Deal found 4/21![Frontier logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 5/26:00 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Deal found 4/21![Spirit Airlines logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 5/246:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Deal found 4/21![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 4/21. 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 5/1911:17 pm
MCO
- BQN
Nonstop2h 45m
Frontier
Deal found 4/21![Frontier logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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 5/86:15 am
MCO
- SJU
1 stop18h 06m
Frontier
Deal found 4/20![Frontier logo]()
$98
This CheapOair deal was found by Cheapflights users on 4/17. 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.
Wed 5/276:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Deal found 4/17![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 5/288:58 pm
MCO
- SJU
1 stop9h 26m
Frontier
Deal found 4/21![Frontier logo]()
$100
This Travelocity deal was found by Cheapflights users on 4/21. 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 5/66:20 am
MCO
- SJU
1 stop9h 30m
Frontier
Deal found 4/21![Frontier logo]()
$101
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 April 22, 2026.
Round-trip from | $168 (eDestinos) |
|---|---|
One-way from | $89 (eDestinos) |
Popular in | December |
Cheapest in | February |
Average price | $247 |
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 22, 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
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Mon 5/11
6:05 am-9:02 am
Nonstop2h 57m
Ponce Mercedita
Fri 5/15
9:47 am-1:02 pm
Nonstop3h 15m
$223
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Thu 5/14
6:10 am-9:07 am
Nonstop2h 57m
Ponce Mercedita
Tue 5/19
10:02 am-1:23 pm
Nonstop3h 21m
$224
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Sat 5/9
6:10 am-9:07 am
Nonstop2h 57m
Ponce Mercedita
Sun 5/10
10:02 am-1:23 pm
Nonstop3h 21m
$226
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 5/8
6:05 am-9:02 am
Nonstop2h 57m
Ponce Mercedita
Sun 5/10
10:02 am-1:23 pm
Nonstop3h 21m
$232
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Sat 6/13
6:45 am-9:42 am
Nonstop2h 57m
Ponce Mercedita
Tue 6/16
10:27 am-1:48 pm
Nonstop3h 21m
$242
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Wed 5/6
7:30 am-10:28 am
Nonstop2h 58m
Ponce Mercedita
Sat 5/9
10:02 am-1:23 pm
Nonstop3h 21m
$244
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 5/15
6:05 am-9:02 am
Nonstop2h 57m
Ponce Mercedita
Mon 5/18
9:47 am-1:02 pm
Nonstop3h 15m
$279
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 5/8
6:05 am-9:02 am
Nonstop2h 57m
Ponce Mercedita
Mon 5/11
9:47 am-1:02 pm
Nonstop3h 15m
$290
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Sat 5/16
6:10 am-9:07 am
Nonstop2h 57m
Ponce Mercedita
Mon 5/18
9:47 am-1:02 pm
Nonstop3h 15m
$302
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Wed 7/15
7:00 am-4:45 pm
1 stop9h 45m
San Juan Luis Munoz Marin Intl
Sat 7/18
2:42 pm-12:15 am
1 stop9h 33m
$354
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-PSE
MCO-SJU
MCO-CPX
MCO-BQN
MCO-MAZ
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-PSE
MCO-SJU
MCO-CPX
MCO-BQN
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 22, 2026.
It’s optimal to fly from Kissimmee to Puerto Rico in the evening. By choosing this option you can save up to 24% 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 April 18, 2026.
Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Sunday at noon when fares are most often at their lowest. Saturday 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 22, 2026.
The most flights from K1S to PR0 are scheduled on a Monday (22 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (10 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 April 22, 2026.
Read through reviews of airlines operating flights from Kissimmee to Puerto Rico, such as Southwest,JetBlue, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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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 April 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 April 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$198 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$228 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$101 | Average$236 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$114 | Average$251 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$380 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$240 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$244 | Average$361 | FlexibilityNo cancel fee | On-time63% |