$80+ Cheap flights from Kissimmee, FL to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Oct 13 — Oct 201
Round-trip
1 adult, Economy
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Find cheap flights from Kissimmee to Puerto Rico with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Kissimmee to Puerto Rico
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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 September 13, 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 September 13, 2026.
This deal was found by Cheapflights users on 9/9. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/159:38 am -
Nonstop2h 52m
Thu 12/172:25 pm -
Nonstop3h 25m
Deal found 9/9![Frontier logo]()
$150
This Booking.com deal was found by Cheapflights users on 9/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2911:00 pm -
Nonstop2h 52m
Sun 10/47:00 am -
Nonstop3h 08m
Deal found 9/9![Frontier logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/285:03 pm -
1 stop7h 56m
Sun 11/17:26 pm -
Nonstop3h 18m
Deal found 9/10![Frontier logo]()
$153
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:03 pm -
1 stop7h 56m
Sat 10/317:23 am -
Nonstop3h 17m
Deal found 9/13![Frontier logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/276:20 am -
Nonstop2h 55m
Fri 11/133:59 pm -
1 stop30h 39m
Deal found 9/10![Frontier logo]()
$155
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 12/39:38 am -
Nonstop2h 52m
Sat 12/122:25 pm -
Nonstop3h 25m
Deal found 9/10![Frontier logo]()
$155
This eDestinos deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/211:00 pm -
Nonstop2h 52m
Sun 10/47:00 am -
Nonstop3h 08m
Deal found 9/11![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:10 pm -
Nonstop3h 03m
Wed 10/76:30 am -
1 stop16h 34m
Deal found 9/9![Frontier logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Mon 10/56:50 am -
1 stop8h 29m
Mon 10/193:55 pm -
Nonstop3h 09m
Deal found 9/10![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:00 pm -
Nonstop2h 53m
Fri 10/3010:20 am -
Nonstop3h 17m
Deal found 9/9![Frontier logo]()
$159
This eDestinos deal was found by Cheapflights users on 9/8. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:36 am -
Nonstop3h 00m
Mon 10/1210:39 am -
Nonstop3h 08m
Deal found 9/8![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:16 am -
Nonstop3h 02m
Wed 10/76:30 am -
1 stop16h 34m
Deal found 9/9![Frontier logo]()
$161
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 September 13, 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 September 13, 2026.
This JetBlue deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/86:25 pm -
1 stop7h 41m
Sun 10/115:01 am -
1 stop6h 13m
Deal found 9/10![JetBlue logo]()
$184
This Super.com deal was found by Cheapflights users on 9/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:35 am -
Nonstop3h 00m
Sun 9/207:00 am -
Nonstop3h 08m
Deal found 9/8![Frontier logo]()
$235
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/116:10 am -
Nonstop2h 45m
Tue 11/176:10 am -
2 stops8h 50m
Deal found 9/10![Southwest logo]()
$275
This CheapOair deal was found by Cheapflights users on 9/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:05 am -
Nonstop2h 56m
Mon 9/2810:05 am -
Nonstop3h 05m
Deal found 9/8![Multiple Airlines logo]()
$288
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:25 pm -
1 stop7h 41m
Sun 10/185:01 am -
1 stop6h 13m
Deal found 9/12![JetBlue logo]()
$199
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:48 pm -
1 stop9h 21m
Wed 10/712:15 am -
1 stop9h 06m
Deal found 9/9![United Airlines logo]()
$425
This JetBlue deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/96:25 pm -
1 stop6h 04m
Thu 10/153:20 am -
1 stop7h 54m
Deal found 9/11![JetBlue logo]()
$218
This Frontier deal was found by Cheapflights users on 9/8. 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.
Mon 10/196:00 am -
Nonstop2h 52m
Fri 10/239:43 am -
Nonstop3h 11m
Deal found 9/8![Frontier logo]()
$244
This JetBlue deal was found by Cheapflights users on 9/13. 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 9/266:00 am -
1 stop10h 12m
Sat 10/36:00 am -
1 stop9h 11m
Deal found 9/13![JetBlue logo]()
$231
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/59:38 am -
Nonstop2h 52m
Tue 12/152:25 pm -
Nonstop3h 25m
Deal found 9/8![Frontier logo]()
$271
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:00 am -
Nonstop2h 55m
Thu 9/243:20 pm -
1 stop7h 20m
Deal found 9/10![Southwest logo]()
$312
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:00 pm -
Nonstop2h 57m
Sun 11/86:25 am -
1 stop6h 32m
Deal found 9/12![JetBlue logo]()
$236
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 10/710:10 am -
2 stops13h 00m
Wed 10/148:15 am -
1 stop10h 25m
Deal found 9/9![Southwest logo]()
$316
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:25 pm -
1 stop6h 04m
Sun 10/183:20 am -
1 stop7h 54m
Deal found 9/12![JetBlue logo]()
$252
This Southwest deal was found by Cheapflights users on 9/9. 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.
Mon 10/122:30 pm -
2 stops9h 40m
Sat 10/175:40 am -
1 stop9h 00m
Deal found 9/9![Southwest logo]()
$316
This JetBlue deal was found by Cheapflights users on 9/13. 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.
Thu 10/157:40 am -
1 stop5h 46m
Mon 11/29:39 pm -
Nonstop3h 05m
Deal found 9/13![JetBlue logo]()
$256
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/317:35 am -
2 stops10h 15m
Mon 11/22:20 pm -
1 stop5h 30m
Deal found 9/10![Southwest logo]()
$318
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:55 pm -
1 stop10h 14m
Sun 10/2512:09 am -
1 stop8h 47m
Deal found 9/9![United Airlines logo]()
$425
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:05 am -
Nonstop2h 55m
Mon 12/145:01 am -
1 stop7h 15m
Deal found 9/12![JetBlue logo]()
$256
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:10 am -
2 stops13h 59m
Sun 10/412:15 am -
1 stop9h 06m
Deal found 9/9![United Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 9/12. 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 9/2210:20 am -
2 stops11h 45m
Sat 9/262:50 pm -
Nonstop3h 05m
Deal found 9/12![Southwest logo]()
$336
This JetBlue deal was found by Cheapflights users on 9/13. 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.
Wed 11/256:35 pm -
1 stop5h 18m
Sat 12/54:10 pm -
1 stop6h 58m
Deal found 9/13![JetBlue logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2711:00 pm -
1 stop9h 34m
Thu 10/15:41 pm -
1 stop20h 11m
Deal found 9/12![Multiple Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:55 pm -
1 stop10h 14m
Sat 10/312:15 am -
1 stop10h 22m
Deal found 9/10![United Airlines logo]()
$446
This JetBlue deal was found by Cheapflights users on 9/13. 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 11/216:35 pm -
1 stop5h 24m
Sat 11/2810:00 am -
Nonstop3h 10m
Deal found 9/13![JetBlue logo]()
$260
This JetBlue deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 12/56:50 pm -
1 stop5h 21m
Tue 12/156:01 am -
1 stop6h 15m
Deal found 9/10![JetBlue logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sun 10/112:36 pm -
1 stop22h 54m
Sun 10/184:55 pm -
1 stop13h 05m
Deal found 9/13![Multiple Airlines logo]()
$590
This JetBlue deal was found by Cheapflights users on 9/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am -
Nonstop2h 47m
Thu 10/82:25 pm -
1 stop7h 49m
Deal found 9/9![JetBlue logo]()
$274
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:54 pm -
1 stop6h 09m
Sat 11/219:45 pm -
Nonstop3h 05m
Deal found 9/12![JetBlue logo]()
$276
This JetBlue deal was found by Cheapflights users on 9/13. 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.
Mon 10/195:01 am -
Nonstop2h 54m
Fri 10/305:01 am -
1 stop6h 56m
Deal found 9/13![JetBlue logo]()
$282
Last-minute flights from Kissimmee to Puerto RicoDiscover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated September 13, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2911:00 pm -
Nonstop2h 52m
Sat 10/310:42 am -
Nonstop3h 10m
Deal found 9/9![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:10 pm -
Nonstop3h 03m
Wed 10/76:30 am -
1 stop16h 34m
Deal found 9/9![Frontier logo]()
$157
This eDestinos deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/211:00 pm -
Nonstop2h 52m
Sun 10/47:00 am -
Nonstop3h 08m
Deal found 9/11![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:16 am -
Nonstop3h 02m
Wed 10/76:30 am -
1 stop16h 34m
Deal found 9/9![Frontier logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Mon 10/56:50 am -
1 stop8h 29m
Mon 10/193:55 pm -
Nonstop3h 09m
Deal found 9/10![Frontier logo]()
$158
This CheapOair deal was found by Cheapflights users on 9/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:50 am -
1 stop8h 29m
Tue 10/62:57 am -
Nonstop3h 02m
Deal found 9/9![Frontier logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:50 am -
1 stop8h 29m
Tue 10/136:42 pm -
Nonstop3h 10m
Deal found 9/8![Frontier logo]()
$163
This eDestinos deal was found by Cheapflights users on 9/8. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:36 am -
Nonstop3h 00m
Mon 10/1210:39 am -
Nonstop3h 08m
Deal found 9/8![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:00 pm -
Nonstop2h 53m
Fri 10/3010:20 am -
Nonstop3h 17m
Deal found 9/9![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/276:20 am -
Nonstop2h 55m
Fri 11/133:59 pm -
1 stop30h 39m
Deal found 9/10![Frontier logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/285:03 pm -
1 stop7h 56m
Sun 11/17:26 pm -
Nonstop3h 18m
Deal found 9/10![Frontier logo]()
$153
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:03 pm -
1 stop7h 56m
Sat 10/317:23 am -
Nonstop3h 17m
Deal found 9/13![Frontier logo]()
$154
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 September 13, 2026.
Search for one-way flight options from Kissimmee to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
This Super.com deal was found by Cheapflights users on 9/13. 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 10/211:00 pm -
Nonstop2h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$80
This Jetabroad deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:35 am -
Nonstop3h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/56:50 am -
1 stop8h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$82
This Super.com deal was found by Cheapflights users on 9/13. 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 10/66:00 am -
1 stop10h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![JetBlue logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/710:45 am -
Nonstop2h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 9/8. 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.
Mon 11/96:00 am -
Nonstop2h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 9/13. 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 10/239:15 am -
1 stop6h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![JetBlue logo]()
$89
This Super.com deal was found by Cheapflights users on 9/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:00 am -
1 stop7h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![JetBlue logo]()
$91
This Super.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:40 pm -
Nonstop3h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/134:53 pm -
2 stops23h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$93
This JetBlue deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Mon 11/96:54 pm -
1 stop5h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/77:25 am -
Nonstop2h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$103
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 September 13, 2026.
Round-trip from | $150 |
|---|---|
One-way from | $80 (Super.com) |
Popular in | December |
Cheapest in | February |
Average price | $246 |
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 7,457,451 searches. Data last updated September 13, 2026.
Use the filters below to find and compare flights from Kissimmee to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Mon 10/5
6:50 am-3:19 pm
1 stop8h 29m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$82
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Tue 10/20
9:30 am-7:53 pm
1 stop10h 23m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$86
OrlandoPonce
MCO Orlando - PSE Ponce Mercedita
MCOPSE
Orlando
Tue 12/8
9:38 am-1:30 pm
Nonstop2h 52m
Ponce Mercedita
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$104
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Sun 11/1
6:40 am-10:30 am
Nonstop2h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Sun 10/4
9:30 am-4:06 pm
1 stop6h 36m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
OrlandoPonce
MCO Orlando - PSE Ponce Mercedita
MCOPSE
Orlando
Fri 11/6
6:54 pm-1:50 am
1 stop5h 56m
Ponce Mercedita
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$112
OrlandoPonce
MCO Orlando - PSE Ponce Mercedita
MCOPSE
Orlando
Fri 10/9
6:25 pm-12:29 am
1 stop6h 04m
Ponce Mercedita
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$112
OrlandoAguadilla
MCO Orlando - BQN Aguadilla Borinquen
MCOBQN
Orlando
Fri 11/6
6:54 pm-2:03 am
1 stop6h 09m
Aguadilla Borinquen
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$116
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Sun 10/11
6:15 am-9:10 am
Nonstop2h 55m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$121
Quickest round-trip
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Tue 12/1
7:55 am-11:40 am
Nonstop2h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$121
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-PSE
MCO-BQN
MCO-CPX
MCO-VQS
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-PSE
MCO-BQN
MCO-CPX
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 September 13, 2026.
It’s optimal to fly from Kissimmee to Puerto Rico in the evening. By choosing this option you can save up to 19% on the cost of your flight, compared to a flight in the afternoon.
Weekly flight availability from Kissimmee to Puerto Rico
Explore weekly flight availability from Kissimmee to Puerto Rico. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 13, 2026.
The most flights from K1S to PR0 are scheduled on a Friday (25 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 on average).
What is the cheapest day to fly from Kissimmee to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Puerto Rico. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Sunday afternoons when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated September 13, 2026.
Read through reviews of airlines operating flights from Kissimmee to Puerto Rico, such as Southwest,Delta, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Kissimmee to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 September 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Kissimmee to Puerto Rico
Discover the top 6 airlines that operate flights from Kissimmee to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$115 | Average$277 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$279 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$161 | Average$363 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$245 | Average$368 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$253 | Average$329 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$253 | Average$386 | FlexibilityNo cancel fee | On-time71% |