$88+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
May 18 — May 251
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 18, 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 18, 2026.
This Trip.com deal was found by Cheapflights users on 4/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:00 am
MCO
- SJU
Nonstop2h 54m
Frontier
Wed 4/294:35 pm
SJU
- MCO
1 stop15h 12m
Frontier
Deal found 4/14![Frontier logo]()
$166
This eDestinos deal was found by Cheapflights users on 4/16. 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 4/305:59 pm
MCO
- SJU
1 stop28h 31m
Frontier
Sun 5/105:15 pm
SJU
- MCO
1 stop13h 25m
Frontier
Deal found 4/16![Frontier logo]()
$168
This Super.com deal was found by Cheapflights users on 4/16. 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 8/68:40 am
MCO
- BQN
Nonstop2h 53m
Frontier
Thu 8/132:59 am
BQN
- MCO
Nonstop2h 53m
Frontier
Deal found 4/16![Frontier logo]()
$169
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 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 4/17![Spirit Airlines logo]()
$170
This Frontier deal was found by Cheapflights users on 4/16. 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 8/811:12 pm
MCO
- BQN
Nonstop2h 52m
Frontier
Thu 8/132:59 am
BQN
- MCO
Nonstop2h 53m
Frontier
Deal found 4/16![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/2811:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Fri 5/12:38 am
BQN
- MCO
Nonstop2h 59m
Frontier
Deal found 4/13![Frontier logo]()
$172
This Super.com deal was found by Cheapflights users on 4/13. 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 4/219:03 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Thu 4/2311:02 am
SJU
- MCO
1 stop12h 27m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$172
This Expedia deal was found by Cheapflights users on 4/13. 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.
Tue 4/2811:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Sat 5/22:48 am
BQN
- MCO
Nonstop2h 59m
Frontier
Deal found 4/13![Frontier logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 4/259:03 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Sat 4/258:27 pm
SJU
- MCO
Nonstop3h 02m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 stop18h 06m
Frontier
Sat 5/166:30 am
SJU
- MCO
1 stop17h 14m
Frontier
Deal found 4/16![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 4/13. 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 4/2211:10 pm
MCO
- SJU
Nonstop2h 51m
Frontier
Thu 4/3010:54 am
SJU
- MCO
Nonstop3h 24m
Frontier
Deal found 4/13![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/74:40 pm
MCO
- SJU
1 stop7h 41m
Frontier
Tue 5/126:30 am
SJU
- MCO
1 stop8h 27m
Frontier
Deal found 4/14![Frontier logo]()
$178
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 18, 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 18, 2026.
This Frontier deal was found by Cheapflights users on 4/16. 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 5/186:05 am
MCO
- PSE
Nonstop2h 57m
Frontier
Wed 5/2011:14 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/16![Frontier logo]()
$206
This Expedia deal was found by Cheapflights users on 4/15. 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.
Fri 5/15:01 am
MCO
- PSE
Nonstop2h 48m
Multiple Airlines
Tue 5/511:14 am
PSE
- MCO
Nonstop3h 21m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 4/16. 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 6/98:00 am
MCO
- SJU
2 stops11h 45m
Southwest
Thu 7/167:00 am
SJU
- MCO
2 stops13h 00m
Southwest
Deal found 4/16![Southwest logo]()
$396
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.
Thu 7/162:05 pm
MCO
- SJU
1 stop6h 40m
Delta
Thu 7/232:42 pm
SJU
- MCO
1 stop9h 16m
Delta
Deal found 4/17![Delta logo]()
$424
This United Airlines deal was found by Cheapflights users on 4/15. 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 5/71:16 pm
MCO
- BQN
1 stop9h 53m
United Airlines
Tue 5/1212:15 am
BQN
- MCO
1 stop9h 43m
United Airlines
Deal found 4/15![United Airlines logo]()
$469
This Frontier deal was found by Cheapflights users on 4/15. 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
Sun 5/1010:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/15![Frontier logo]()
$249
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:01 am
MCO
- PSE
Nonstop2h 48m
Multiple Airlines
Mon 5/119:47 am
PSE
- MCO
Nonstop3h 15m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$271
This JetBlue deal was found by Cheapflights users on 4/13. 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 5/165:01 am
MCO
- BQN
Nonstop2h 39m
JetBlue
Tue 5/195:01 am
BQN
- MCO
1 stop11h 56m
JetBlue
Deal found 4/13![JetBlue logo]()
$543
This Frontier deal was found by Cheapflights users on 4/13. 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 6/16:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Wed 6/1011:41 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/13![Frontier logo]()
$262
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:01 am
MCO
- PSE
Nonstop2h 48m
Multiple Airlines
Thu 5/710:02 am
PSE
- MCO
Nonstop3h 21m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$289
This Frontier deal was found by Cheapflights users on 4/13. 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 5/296:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Wed 6/1011:41 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/13![Frontier logo]()
$270
This Frontier deal was found by Cheapflights users on 4/16. 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 5/166:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Mon 5/189:47 am
PSE
- MCO
Nonstop3h 15m
Frontier
Deal found 4/16![Frontier logo]()
$279
This Southwest deal was found by Cheapflights users on 4/13. 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 4/249:05 pm
MCO
- SJU
Nonstop2h 50m
Southwest
Mon 4/275:05 am
SJU
- MCO
Nonstop3h 15m
Southwest
Deal found 4/13![Southwest logo]()
$401
This Frontier 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 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
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 4/13. 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
Mon 7/65:30 am
SJU
- MCO
1 stop7h 20m
Southwest
Deal found 4/13![Southwest logo]()
$410
This Super.com deal was found by Cheapflights users on 4/13. 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 5/226:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Tue 5/2610:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/13![Frontier logo]()
$283
This Southwest deal was found by Cheapflights users on 4/13. 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 7/49:00 am
MCO
- SJU
2 stops11h 40m
Southwest
Sat 7/116:30 am
SJU
- MCO
2 stops8h 30m
Southwest
Deal found 4/13![Southwest logo]()
$410
This Expedia deal was found by Cheapflights users on 4/13. 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.
Wed 5/207:30 am
MCO
- PSE
Nonstop2h 58m
Frontier
Tue 5/2610:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/13![Frontier logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 4/306:00 am
MCO
- MAZ
1 stop6h 44m
Multiple Airlines
Tue 5/54:36 pm
MAZ
- MCO
1 stop13h 26m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$445
This JetBlue deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:55 pm
MCO
- MAZ
1 stop5h 48m
JetBlue
Mon 5/44:36 pm
MAZ
- MCO
1 stop8h 23m
JetBlue
Deal found 4/14![JetBlue logo]()
$548
This Southwest deal was found by Cheapflights users on 4/12. 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 4/219:10 am
MCO
- SJU
2 stops13h 30m
Southwest
Wed 4/225:05 am
SJU
- MCO
1 stop10h 55m
Southwest
Deal found 4/12![Southwest logo]()
$425
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.
Sat 6/209:38 am
MCO
- SJU
1 stop7h 55m
Frontier
Tue 6/235:15 pm
SJU
- MCO
1 stop13h 30m
Frontier
Deal found 4/17![Frontier logo]()
$292
This JetBlue deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:01 am
MCO
- BQN
Nonstop2h 39m
JetBlue
Thu 5/145:01 am
BQN
- MCO
1 stop11h 56m
JetBlue
Deal found 4/13![JetBlue logo]()
$553
This Southwest deal was found by Cheapflights users on 4/15. 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 5/610:15 am
MCO
- SJU
2 stops12h 25m
Southwest
Wed 5/275:05 am
SJU
- MCO
2 stops9h 55m
Southwest
Deal found 4/15![Southwest logo]()
$425
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.
Wed 4/221:19 pm
MCO
- BQN
1 stop9h 50m
United Airlines
Sat 4/2512:15 am
BQN
- MCO
1 stop10h 43m
United Airlines
Deal found 4/17![United Airlines logo]()
$626
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 4/257:55 pm
MCO
- MAZ
1 stop13h 47m
Multiple Airlines
Sun 4/264:36 pm
MAZ
- MCO
2 stops15h 11m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$476
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Tue 5/2610:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/17![Frontier logo]()
$307
This KAYAK deal was found by Cheapflights users on 4/15. 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.
Tue 5/195:01 am
MCO
- MAZ
1 stop7h 43m
JetBlue
Sun 5/244:36 pm
MAZ
- MCO
1 stop8h 14m
JetBlue
Deal found 4/15![JetBlue logo]()
$566
This Southwest deal was found by Cheapflights users on 4/13. 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 5/110:15 am
MCO
- SJU
1 stop5h 20m
Southwest
Mon 5/45:35 am
SJU
- MCO
2 stops10h 45m
Southwest
Deal found 4/13![Southwest logo]()
$426
This Mytrip deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
MCO
- CPX
1 stop8h 43m
Multiple Airlines
Mon 5/44:33 pm
CPX
- MCO
2 stops25h 03m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$479
Last-minute flights from Kissimmee to Puerto RicoDiscover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated April 18, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 4/13. 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 4/1611:10 pm
MCO
- SJU
Nonstop2h 51m
Frontier
Thu 4/233:39 pm
SJU
- MCO
Nonstop3h 29m
Frontier
Deal found 4/13![Frontier logo]()
$179
This Super.com deal was found by Cheapflights users on 4/13. 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 4/219:03 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Thu 4/2311:02 am
SJU
- MCO
1 stop12h 27m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$172
This Trip.com deal was found by Cheapflights users on 4/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:00 am
MCO
- SJU
Nonstop2h 54m
Frontier
Wed 4/294:35 pm
SJU
- MCO
1 stop15h 12m
Frontier
Deal found 4/14![Frontier logo]()
$166
This Frontier deal was found by Cheapflights users on 4/13. 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 4/227:00 am
MCO
- SJU
Nonstop2h 54m
Frontier
Tue 4/286:30 am
SJU
- MCO
Nonstop3h 29m
Frontier
Deal found 4/13![Frontier logo]()
$176
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 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 4/17![Spirit Airlines logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 4/259:03 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Sat 4/258:27 pm
SJU
- MCO
Nonstop3h 02m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 4/257:00 am
MCO
- SJU
Nonstop2h 54m
Frontier
Sat 5/96:30 am
SJU
- MCO
1 stop9h 05m
Frontier
Deal found 4/16![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/2811:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Fri 5/12:38 am
BQN
- MCO
Nonstop2h 59m
Frontier
Deal found 4/13![Frontier logo]()
$172
This Expedia deal was found by Cheapflights users on 4/13. 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.
Tue 4/2811:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Sat 5/22:48 am
BQN
- MCO
Nonstop2h 59m
Frontier
Deal found 4/13![Frontier logo]()
$174
This eDestinos deal was found by Cheapflights users on 4/16. 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 4/305:59 pm
MCO
- SJU
1 stop28h 31m
Frontier
Sun 5/105:15 pm
SJU
- MCO
1 stop13h 25m
Frontier
Deal found 4/16![Frontier logo]()
$168
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 stop18h 06m
Frontier
Sat 5/166:30 am
SJU
- MCO
1 stop17h 14m
Frontier
Deal found 4/16![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/74:40 pm
MCO
- SJU
1 stop7h 41m
Frontier
Tue 5/126:30 am
SJU
- MCO
1 stop8h 27m
Frontier
Deal found 4/14![Frontier logo]()
$178
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 18, 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 18, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:15 am
MCO
- SJU
1 stop18h 06m
Frontier
Deal found 4/14![Frontier logo]()
$88
This eDestinos deal was found by Cheapflights users on 4/16. 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 5/29:04 am
MCO
- SJU
1 stop15h 25m
Frontier
Deal found 4/16![Frontier logo]()
$89
This eDestinos deal was found by Cheapflights users on 4/13. 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 4/237:00 am
MCO
- SJU
Nonstop2h 54m
Frontier
Deal found 4/13![Frontier logo]()
$90
This eDestinos deal was found by Cheapflights users on 4/15. 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 5/3011:37 am
MCO
- SJU
1 stop16h 24m
Frontier
Deal found 4/15![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 6/156:45 am
MCO
- PSE
Nonstop2h 57m
Frontier
Deal found 4/14![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 4/14. 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 4/252:29 pm
MCO
- SJU
1 stop10h 25m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 stop21h 46m
Frontier
Deal found 4/14![Frontier logo]()
$94
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 5/18:34 pm
MCO
- SJU
Nonstop2h 50m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$95
This Super.com deal was found by Cheapflights users on 4/15. 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.
Sun 5/108:40 am
MCO
- BQN
Nonstop2h 51m
Frontier
Deal found 4/15![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/166:15 am
MCO
- SJU
1 stop17h 44m
Frontier
Deal found 4/15![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/216:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Deal found 4/15![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 4/14. 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 5/611:17 pm
MCO
- BQN
Nonstop2h 45m
Frontier
Deal found 4/14![Frontier logo]()
$97
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 18, 2026.
Round-trip from | $168 (eDestinos) |
|---|---|
One-way from | $88 (Cheapflightsfares) |
Popular in | December |
Cheapest in | February |
Average price | $250 |
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 18, 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 5/18
6:05 am-9:02 am
Nonstop2h 57m
Ponce Mercedita
Wed 5/20
11:14 am-2:35 pm
Nonstop3h 21m
$206
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Wed 5/6
7:30 am-10:28 am
Nonstop2h 58m
Ponce Mercedita
Sun 5/10
10:02 am-1:23 pm
Nonstop3h 21m
$249
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 5/1
5:01 am-7:49 am
Nonstop2h 48m
Ponce Mercedita
Tue 5/5
11:14 am-2:35 pm
Nonstop3h 21m
$251
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Mon 6/1
6:10 am-9:07 am
Nonstop2h 57m
Ponce Mercedita
Wed 6/10
11:41 am-3:02 pm
Nonstop3h 21m
$262
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 5/29
6:10 am-9:07 am
Nonstop2h 57m
Ponce Mercedita
Wed 6/10
11:41 am-3:02 pm
Nonstop3h 21m
$270
Quickest round-trip
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Tue 4/28
5:01 am-7:49 am
Nonstop2h 48m
Ponce Mercedita
Mon 5/11
9:47 am-1:02 pm
Nonstop3h 15m
$271
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
$279
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Thu 5/14
6:10 am-9:07 am
Nonstop2h 57m
Ponce Mercedita
Mon 5/18
9:47 am-1:02 pm
Nonstop3h 15m
$279
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 5/22
6:10 am-9:07 am
Nonstop2h 57m
Ponce Mercedita
Tue 5/26
10:02 am-1:23 pm
Nonstop3h 21m
$283
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Wed 5/20
7:30 am-10:28 am
Nonstop2h 58m
Ponce Mercedita
Tue 5/26
10:02 am-1:23 pm
Nonstop3h 21m
$287
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-SJU
MCO-BQN
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-SJU
MCO-BQN
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 April 18, 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 11, 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 18, 2026.
The most flights from K1S to PR0 are scheduled on a Wednesday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated April 18, 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.
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
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 18, 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 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$197 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$99 | Average$229 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$101 | Average$235 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$114 | Average$251 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$356 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$240 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$244 | Average$362 | FlexibilityNo cancel fee | On-time63% |