$72+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
May 9 — May 161
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 9, 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 9, 2026.
This Frontier deal was found by Cheapflights users on 4/4. 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 4/3011:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Sat 5/92:59 am
BQN
- MCO
Nonstop2h 58m
Frontier
Deal found 4/4![Frontier logo]()
$166
This eDestinos deal was found by Cheapflights users on 4/5. 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 4/116:00 am
MCO
- SJU
Nonstop2h 53m
Frontier
Mon 4/136:00 am
SJU
- MCO
1 stop8h 14m
Frontier
Deal found 4/5![Frontier logo]()
$168
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 4/157:55 pm
MCO
- SJU
Nonstop2h 53m
Frontier
Tue 4/213:08 am
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 4/6![Frontier logo]()
$169
This Frontier deal was found by Cheapflights users on 4/6. 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 4/108:47 pm
MCO
- SJU
Nonstop2h 53m
Frontier
Tue 4/143:08 am
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 4/6![Frontier logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 4/5. 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 4/1111:10 pm
MCO
- SJU
Nonstop2h 51m
Frontier
Sat 4/183:21 am
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 4/5![Frontier logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 4/228:34 pm
MCO
- SJU
Nonstop2h 50m
Spirit Airlines
Sat 4/258:27 pm
SJU
- MCO
Nonstop3h 02m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$172
This Orbitz deal was found by Cheapflights users on 4/6. 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 4/1811:10 pm
MCO
- SJU
Nonstop2h 51m
Multiple Airlines
Tue 4/2112:57 pm
SJU
- MCO
Nonstop3h 13m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$173
This Super.com deal was found by Cheapflights users on 4/6. 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 6/2311:12 pm
MCO
- BQN
Nonstop2h 52m
Frontier
Sat 6/272:59 am
BQN
- MCO
Nonstop2h 53m
Frontier
Deal found 4/6![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/1011:10 pm
MCO
- SJU
Nonstop2h 51m
Multiple Airlines
Sat 4/111:45 am
SJU
- MCO
Nonstop3h 15m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 5/15:05 am
MCO
- SJU
1 stop19h 24m
Frontier
Tue 5/58:30 am
SJU
- MCO
1 stop13h 27m
Frontier
Deal found 4/6![Frontier logo]()
$175
This Booking.com deal was found by Cheapflights users on 4/7. 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.
Sun 5/311:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Mon 5/42:59 am
BQN
- MCO
Nonstop2h 58m
Frontier
Deal found 4/7![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 4/8. 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 4/303:45 pm
MCO
- SJU
1 stop8h 14m
Frontier
Thu 5/73:12 pm
SJU
- MCO
1 stop8h 32m
Frontier
Deal found 4/8![Frontier logo]()
$176
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 9, 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 9, 2026.
This Spirit deal was found by Cheapflights users on 4/8. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:30 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Tue 4/287:01 pm
SJU
- MCO
Nonstop3h 13m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$189
This CheapOair deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:55 am
MCO
- PSE
Nonstop2h 57m
Frontier
Tue 6/1610:37 am
PSE
- MCO
Nonstop3h 22m
Frontier
Deal found 4/7![Frontier logo]()
$189
This Expedia deal was found by Cheapflights users on 4/5. 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 4/197:35 am
MCO
- PSE
Nonstop2h 51m
Multiple Airlines
Wed 4/228:39 am
PSE
- MCO
Nonstop3h 11m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 4/5. 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 5/307:20 am
MCO
- SJU
2 stops15h 55m
Southwest
Fri 6/55:30 am
SJU
- MCO
2 stops12h 30m
Southwest
Deal found 4/5![Southwest logo]()
$334
This Frontier deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:30 am
MCO
- PSE
Nonstop2h 58m
Frontier
Sun 5/1010:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/9![Frontier logo]()
$194
This JetBlue deal was found by Cheapflights users on 4/5. 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 4/211:57 pm
MCO
- BQN
1 stop11h 39m
JetBlue
Mon 4/278:30 am
BQN
- MCO
Nonstop2h 59m
JetBlue
Deal found 4/5![JetBlue logo]()
$443
This United Airlines deal was found by Cheapflights users on 4/4. 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.
Sat 6/132:05 pm
MCO
- BQN
1 stop9h 04m
United Airlines
Mon 6/1512:15 am
BQN
- MCO
1 stop9h 01m
United Airlines
Deal found 4/4![United Airlines logo]()
$455
This Super.com deal was found by Cheapflights users on 4/7. 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 5/67:30 am
MCO
- PSE
Nonstop2h 58m
Frontier
Tue 5/1910:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/7![Frontier logo]()
$208
This CheapOair deal was found by Cheapflights users on 4/7. 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
Tue 5/1910:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/7![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 4/5. 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 5/17:45 am
MCO
- PSE
Nonstop2h 51m
Frontier
Thu 5/710:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/5![Frontier logo]()
$239
This Southwest deal was found by Cheapflights users on 4/6. 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 6/53:20 pm
MCO
- SJU
2 stops8h 55m
Southwest
Wed 6/105:00 am
SJU
- MCO
2 stops9h 40m
Southwest
Deal found 4/6![Southwest logo]()
$334
This Frontier deal was found by Cheapflights users on 4/5. 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
Thu 5/2810:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/5![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 4/1711:10 pm
MCO
- MAZ
1 stop10h 32m
Multiple Airlines
Tue 4/214:36 pm
MAZ
- MCO
1 stop5h 38m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 4/7. 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 4/272:00 pm
MCO
- SJU
2 stops9h 40m
Southwest
Wed 5/135:05 am
SJU
- MCO
2 stops12h 50m
Southwest
Deal found 4/7![Southwest logo]()
$352
This CheapOair deal was found by Cheapflights users on 4/7. 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 6/126:55 am
MCO
- PSE
Nonstop2h 57m
Frontier
Tue 6/1610:37 am
PSE
- MCO
Nonstop3h 22m
Frontier
Deal found 4/7![Frontier logo]()
$245
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:00 pm
MCO
- SJU
2 stops9h 40m
Southwest
Mon 5/45:35 am
SJU
- MCO
2 stops10h 45m
Southwest
Deal found 4/9![Southwest logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 4/4. 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
Tue 5/2610:02 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/4![Frontier logo]()
$249
This Southwest deal was found by Cheapflights users on 4/7. 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
Sun 7/125:20 am
SJU
- MCO
1 stop7h 10m
Southwest
Deal found 4/7![Southwest logo]()
$354
This Frontier deal was found by Cheapflights users on 4/4. 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 4/177:40 am
MCO
- PSE
Nonstop2h 51m
Frontier
Sun 4/1911:21 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/4![Frontier logo]()
$250
This JetBlue deal was found by Cheapflights users on 4/7. 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 4/7![JetBlue logo]()
$503
This Southwest deal was found by Cheapflights users on 4/8. 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 5/69:10 am
MCO
- SJU
2 stops13h 30m
Southwest
Wed 5/135:05 am
SJU
- MCO
2 stops14h 05m
Southwest
Deal found 4/8![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 4/7. 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.
Fri 4/172:57 pm
MCO
- BQN
1 stop8h 12m
United Airlines
Sat 4/1812:15 am
BQN
- MCO
1 stop10h 43m
United Airlines
Deal found 4/7![United Airlines logo]()
$529
This Frontier deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Wed 5/2011:14 am
PSE
- MCO
Nonstop3h 21m
Frontier
Deal found 4/9![Frontier logo]()
$267
This Southwest deal was found by Cheapflights users on 4/4. 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 6/223:20 pm
MCO
- SJU
2 stops8h 55m
Southwest
Wed 7/15:00 am
SJU
- MCO
2 stops9h 05m
Southwest
Deal found 4/4![Southwest logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 5/147:30 am
MCO
- MAZ
1 stop5h 14m
Multiple Airlines
Sun 5/174:36 pm
MAZ
- MCO
1 stop13h 34m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$552
This KAYAK deal was found by Cheapflights users on 4/7. 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.
Fri 5/88:00 am
MCO
- MAZ
1 stop8h 11m
JetBlue
Sun 5/107:35 am
MAZ
- MCO
1 stop8h 32m
JetBlue
Deal found 4/7![JetBlue logo]()
$566
This Southwest deal was found by Cheapflights users on 4/5. 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 7/63:20 pm
MCO
- SJU
2 stops8h 55m
Southwest
Fri 7/105:30 am
SJU
- MCO
1 stop8h 25m
Southwest
Deal found 4/5![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 4/8. 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.
Fri 4/242:57 pm
MCO
- BQN
1 stop8h 12m
United Airlines
Mon 4/2712:15 am
BQN
- MCO
1 stop9h 43m
United Airlines
Deal found 4/8![United Airlines logo]()
$622
This JetBlue deal was found by Cheapflights users on 4/4. 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 4/155:01 am
MCO
- MAZ
1 stop4h 41m
JetBlue
Sun 4/191:19 pm
MAZ
- MCO
1 stop8h 37m
JetBlue
Deal found 4/4![JetBlue logo]()
$568
This Kiwi.com deal was found by Cheapflights users on 4/5. 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.
Wed 4/1511:10 am
MCO
- VQS
1 stop6h 35m
Multiple Airlines
Wed 4/294:13 pm
VQS
- MCO
1 stop7h 16m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$624
Last-minute flights from Kissimmee to Puerto RicoDiscover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated April 9, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 4/5. 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 4/88:25 am
MCO
- SJU
1 stop11h 25m
Spirit Airlines
Wed 4/228:27 pm
SJU
- MCO
Nonstop3h 02m
Spirit Airlines
Deal found 4/5![Spirit Airlines logo]()
$177
This Frontier deal was found by Cheapflights users on 4/6. 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 4/108:47 pm
MCO
- SJU
Nonstop2h 53m
Frontier
Tue 4/143:08 am
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 4/6![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/1011:10 pm
MCO
- SJU
Nonstop2h 51m
Multiple Airlines
Sat 4/111:45 am
SJU
- MCO
Nonstop3h 15m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$174
This eDestinos deal was found by Cheapflights users on 4/5. 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 4/116:00 am
MCO
- SJU
Nonstop2h 53m
Frontier
Mon 4/136:00 am
SJU
- MCO
1 stop8h 14m
Frontier
Deal found 4/5![Frontier logo]()
$168
This Cheapflightsfares deal was found by Cheapflights users on 4/5. 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 4/1111:10 pm
MCO
- SJU
Nonstop2h 51m
Frontier
Sat 4/183:21 am
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 4/5![Frontier logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 4/157:55 pm
MCO
- SJU
Nonstop2h 53m
Frontier
Tue 4/213:08 am
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 4/6![Frontier logo]()
$169
This Orbitz deal was found by Cheapflights users on 4/6. 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 4/1811:10 pm
MCO
- SJU
Nonstop2h 51m
Multiple Airlines
Tue 4/2112:57 pm
SJU
- MCO
Nonstop3h 13m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 4/229:03 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Fri 5/12:59 am
SJU
- MCO
Nonstop3h 03m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$172
This Frontier deal was found by Cheapflights users on 4/4. 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 4/3011:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Sat 5/92:59 am
BQN
- MCO
Nonstop2h 58m
Frontier
Deal found 4/4![Frontier logo]()
$166
This Frontier deal was found by Cheapflights users on 4/8. 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 4/303:45 pm
MCO
- SJU
1 stop8h 14m
Frontier
Tue 5/58:30 am
SJU
- MCO
1 stop13h 27m
Frontier
Deal found 4/8![Frontier logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 5/15:05 am
MCO
- SJU
1 stop19h 24m
Frontier
Tue 5/58:30 am
SJU
- MCO
1 stop13h 27m
Frontier
Deal found 4/6![Frontier logo]()
$175
This Booking.com deal was found by Cheapflights users on 4/7. 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.
Sun 5/311:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Mon 5/42:59 am
BQN
- MCO
Nonstop2h 58m
Frontier
Deal found 4/7![Frontier logo]()
$176
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 9, 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 9, 2026.
This Frontier deal was found by Cheapflights users on 4/5. 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 4/2511:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Deal found 4/5![Frontier logo]()
$72
This Super.com deal was found by Cheapflights users on 4/6. 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 5/1511:17 pm
MCO
- BQN
Nonstop2h 45m
Frontier
Deal found 4/6![Frontier logo]()
$78
This Frontier deal was found by Cheapflights users on 4/6. 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 5/108:40 am
MCO
- BQN
Nonstop2h 51m
Frontier
Deal found 4/6![Frontier logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 6/98:40 am
MCO
- BQN
Nonstop2h 53m
Frontier
Deal found 4/6![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 5/211:00 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Deal found 4/4![Frontier logo]()
$87
This Super.com deal was found by Cheapflights users on 4/6. 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 5/24:36 pm
MCO
- SJU
1 stop7h 53m
Frontier
Deal found 4/6![Frontier logo]()
$87
This Frontier deal was found by Cheapflights users on 4/5. 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
Deal found 4/5![Frontier logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 4/7. 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 4/226:30 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$88
This Frontier deal was found by Cheapflights users on 4/8. 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 4/2311:15 pm
MCO
- BQN
Nonstop2h 43m
Frontier
Deal found 4/8![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 4/6. 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 5/89:24 pm
MCO
- SJU
Nonstop2h 55m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$89
This CheapOair deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:10 am
MCO
- PSE
Nonstop2h 57m
Frontier
Deal found 4/4![Frontier logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/288:00 am
MCO
- SJU
1 stop16h 29m
Frontier
Deal found 4/6![Frontier logo]()
$90
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 9, 2026.
Round-trip from | $166 (Frontier) |
|---|---|
One-way from | $72 (Frontier) |
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 9, 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
Quickest round-trip
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Sat 4/25
6:30 am-9:19 am
Nonstop2h 49m
San Juan Luis Munoz Marin Intl
Tue 4/28
7:01 pm-10:14 pm
Nonstop3h 13m
$189
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Thu 6/11
6:55 am-9:52 am
Nonstop2h 57m
Ponce Mercedita
Tue 6/16
10:37 am-1:59 pm
Nonstop3h 22m
$189
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Tue 5/5
7:30 am-10:28 am
Nonstop2h 58m
Ponce Mercedita
Sun 5/10
10:02 am-1:23 pm
Nonstop3h 21m
$194
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Wed 5/6
7:30 am-10:28 am
Nonstop2h 58m
Ponce Mercedita
Tue 5/19
10:02 am-1:23 pm
Nonstop3h 21m
$208
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 5/15
6:05 am-9:02 am
Nonstop2h 57m
Ponce Mercedita
Tue 5/19
10:02 am-1:23 pm
Nonstop3h 21m
$237
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 5/1
7:45 am-10:36 am
Nonstop2h 51m
Ponce Mercedita
Thu 5/7
10:02 am-1:23 pm
Nonstop3h 21m
$239
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Thu 5/21
6:10 am-9:07 am
Nonstop2h 57m
Ponce Mercedita
Thu 5/28
10:02 am-1:23 pm
Nonstop3h 21m
$239
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 6/12
6:55 am-9:52 am
Nonstop2h 57m
Ponce Mercedita
Tue 6/16
10:37 am-1:59 pm
Nonstop3h 22m
$245
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Thu 5/21
6:10 am-9:07 am
Nonstop2h 57m
Ponce Mercedita
Tue 5/26
10:02 am-1:23 pm
Nonstop3h 21m
$249
OrlandoPonce
MCO - PSE
MCOPSE
Orlando
Fri 4/17
7:40 am-10:31 am
Nonstop2h 51m
Ponce Mercedita
Sun 4/19
11:21 am-2:42 pm
Nonstop3h 21m
$250
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-CPX
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-BQN
MCO-SJU
MCO-PSE
MCO-CPX
What is the cheapest month to book a flight from Kissimmee to Puerto Rico?
Currently, August is the cheapest month in which you can book a flight from Kissimmee to Puerto Rico (average of $53). Flying from Kissimmee to Puerto Rico in December is currently the most expensive (average of $124). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from K1S to PR?
Find hourly flight availability from Kissimmee to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 9, 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 4, 2026.
Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Thursday at noon when fares are most often at their lowest. Sunday evenings 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 9, 2026.
The most flights from K1S to PR0 are scheduled on a Thursday (25 on average). You will have fewer flight options on Tuesday, 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 9, 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.
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
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 9, 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 9, 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$100 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$114 | Average$251 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$351 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$240 | Average$435 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$362 | FlexibilityNo cancel fee | On-time63% |