$84+ Cheap flights from Kissimmee, FL to Puerto Rico
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Sep 30 — Oct 71
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 August 31, 2026.
Explore the most affordable flight options available from Kissimmee to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 31, 2026.
This Priceline deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:25 am -
Nonstop2h 52m
Wed 11/412:22 pm -
Nonstop3h 04m
Deal found 8/31![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:36 am -
Nonstop3h 00m
Mon 10/265:11 pm -
1 stop18h 38m
Deal found 8/31![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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
Mon 11/23:59 pm -
1 stop17h 11m
Deal found 8/28![Frontier logo]()
$166
This CheapOair deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Sun 9/137:19 am -
Nonstop2h 54m
Sat 9/1911:12 am -
Nonstop2h 56m
Deal found 8/28![Frontier logo]()
$167
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/106:35 am -
Nonstop3h 00m
Mon 9/217:00 am -
Nonstop3h 08m
Deal found 8/27![Frontier logo]()
$167
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:10 pm -
Nonstop3h 03m
Mon 9/212:57 am -
Nonstop3h 02m
Deal found 8/31![Frontier logo]()
$168
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/911:00 pm -
Nonstop2h 53m
Mon 10/127:20 am -
Nonstop3h 11m
Deal found 8/27![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/86:20 am -
Nonstop2h 58m
Mon 10/125:11 pm -
1 stop14h 57m
Deal found 8/27![Frontier logo]()
$170
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/137:19 am -
Nonstop2h 54m
Sun 9/2011:08 am -
Nonstop2h 56m
Deal found 8/28![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:35 am -
Nonstop3h 00m
Wed 10/76:30 am -
1 stop16h 34m
Deal found 8/31![Frontier logo]()
$171
This Super.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:19 am -
Nonstop2h 54m
Tue 9/1510:52 am -
Nonstop2h 56m
Deal found 8/29![Frontier logo]()
$172
This Cheapflightsfares deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates ” 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 11/111:00 pm -
Nonstop2h 50m
Fri 11/63:55 am -
Nonstop3h 06m
Deal found 8/28![Frontier logo]()
$172
Best flights from Kissimmee to Puerto RicoDiscover carefully curated flight deals from Kissimmee to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
Discover carefully curated flight deals from Kissimmee to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:50 pm -
2 stops9h 20m
Sun 11/15:35 am -
Nonstop3h 10m
Deal found 8/30![Southwest logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2511:16 am -
1 stop4h 55m
Mon 9/287:35 am -
1 stop22h 24m
Deal found 8/27![Multiple Airlines logo]()
$243
This JetBlue deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/195:05 am -
Nonstop2h 56m
Sat 9/268:55 am -
Nonstop3h 06m
Deal found 8/28![JetBlue logo]()
$283
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:20 pm -
1 stop8h 49m
Sat 9/1212:15 am -
1 stop9h 06m
Deal found 8/31![United Airlines logo]()
$326
This CheapOair deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/305:05 am -
Nonstop2h 56m
Sun 10/410:05 am -
Nonstop3h 05m
Deal found 8/26![Multiple Airlines logo]()
$250
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/31:45 pm -
2 stops8h 25m
Wed 10/75:50 am -
2 stops13h 55m
Deal found 8/27![Southwest logo]()
$280
This JetBlue deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/285:30 am -
Nonstop2h 52m
Sun 11/110:12 am -
Nonstop3h 15m
Deal found 8/27![JetBlue logo]()
$283
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2812:45 pm -
2 stops10h 10m
Mon 10/55:30 am -
1 stop8h 35m
Deal found 8/31![Southwest logo]()
$280
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:48 pm -
1 stop9h 21m
Sat 10/1012:15 am -
1 stop9h 06m
Deal found 8/30![United Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/53:10 pm -
1 stop8h 55m
Sat 11/76:45 am -
2 stops14h 45m
Deal found 8/27![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:45 am -
1 stop9h 15m
Tue 10/135:50 am -
2 stops10h 45m
Deal found 8/28![Southwest logo]()
$280
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:20 pm -
1 stop8h 49m
Mon 9/2112:15 am -
1 stop9h 06m
Deal found 8/31![United Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/261:10 pm -
2 stops8h 50m
Sat 10/35:40 am -
1 stop8h 10m
Deal found 8/27![Southwest logo]()
$280
This Priceline deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Wed 10/145:01 am -
Nonstop2h 54m
Fri 10/163:20 am -
1 stop18h 54m
Deal found 8/26![JetBlue logo]()
$383
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:55 pm -
1 stop10h 14m
Sun 10/412:15 am -
1 stop9h 06m
Deal found 8/31![United Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1711:00 pm -
1 stop12h 26m
Mon 9/215:59 pm -
2 stops15h 54m
Deal found 8/27![Multiple Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1612:55 pm -
1 stop10h 14m
Fri 10/2312:15 am -
1 stop9h 06m
Deal found 8/29![United Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:35 pm -
1 stop8h 25m
Wed 10/75:50 am -
2 stops12h 15m
Deal found 8/30![Southwest logo]()
$290
This JetBlue deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:25 pm -
Nonstop2h 56m
Tue 12/85:01 am -
Nonstop3h 09m
Deal found 8/30![JetBlue logo]()
$398
This CheapOair deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Sun 10/116:00 am -
Nonstop2h 52m
Sat 10/173:20 am -
2 stops19h 39m
Deal found 8/26![Multiple Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:00 am -
2 stops11h 55m
Fri 9/115:30 am -
1 stop7h 40m
Deal found 8/29![Southwest logo]()
$291
This JetBlue deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Sun 10/115:01 am -
Nonstop2h 54m
Sat 10/173:20 am -
1 stop7h 54m
Deal found 8/27![JetBlue logo]()
$418
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/1012:45 pm -
2 stops10h 25m
Wed 9/166:00 am -
2 stops16h 05m
Deal found 8/28![Southwest logo]()
$296
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/912:55 pm -
1 stop10h 14m
Sat 10/1012:15 am -
1 stop9h 06m
Deal found 8/28![United Airlines logo]()
$396
This JetBlue deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:05 am -
Nonstop2h 56m
Sun 10/255:01 am -
1 stop6h 56m
Deal found 8/30![JetBlue logo]()
$418
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/37:15 pm -
Nonstop3h 00m
Sun 9/66:00 am -
2 stops11h 45m
Deal found 8/27![Southwest logo]()
$296
This JetBlue deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:05 am -
Nonstop2h 56m
Mon 10/265:01 am -
1 stop6h 56m
Deal found 8/30![JetBlue logo]()
$418
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:20 pm -
1 stop8h 49m
Wed 9/2312:15 am -
1 stop10h 22m
Deal found 8/29![United Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/69:30 am -
2 stops13h 50m
Thu 9/103:20 pm -
1 stop7h 20m
Deal found 8/31![Southwest logo]()
$298
This JetBlue deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:50 pm -
1 stop5h 21m
Wed 12/95:01 am -
Nonstop3h 09m
Deal found 8/30![JetBlue logo]()
$478
Last-minute flights from Kissimmee to Puerto RicoDiscover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Puerto Rico. Data last updated August 31, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:44 pm -
Nonstop3h 05m
Mon 10/56:42 pm -
Nonstop3h 10m
Deal found 8/31![Frontier logo]()
$170
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/106:35 am -
Nonstop3h 00m
Mon 9/217:00 am -
Nonstop3h 08m
Deal found 8/27![Frontier logo]()
$167
This Super.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:19 am -
Nonstop2h 54m
Tue 9/1510:52 am -
Nonstop2h 56m
Deal found 8/29![Frontier logo]()
$172
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1111:16 am -
Nonstop3h 02m
Wed 9/1610:42 am -
Nonstop3h 10m
Deal found 8/27![Frontier logo]()
$173
This CheapOair deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Sun 9/137:19 am -
Nonstop2h 54m
Sat 9/1911:12 am -
Nonstop2h 56m
Deal found 8/28![Frontier logo]()
$167
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/137:19 am -
Nonstop2h 54m
Sun 9/2011:08 am -
Nonstop2h 56m
Deal found 8/28![Frontier logo]()
$171
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:10 pm -
Nonstop3h 03m
Mon 9/212:57 am -
Nonstop3h 02m
Deal found 8/31![Frontier logo]()
$168
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/1811:16 am -
Nonstop3h 02m
Sat 9/1910:42 am -
Nonstop3h 10m
Deal found 8/28![Frontier logo]()
$169
This Booking.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:00 pm -
Nonstop2h 49m
Sun 9/2011:08 am -
Nonstop2h 56m
Deal found 8/30![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:35 am -
Nonstop3h 00m
Wed 9/236:42 pm -
Nonstop3h 10m
Deal found 8/31![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:00 pm -
Nonstop2h 52m
Mon 9/284:39 pm -
2 stops24h 30m
Deal found 8/31![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:35 am -
Nonstop3h 00m
Wed 10/76:30 am -
1 stop16h 34m
Deal found 8/31![Frontier logo]()
$171
One-way flights from Kissimmee to Puerto RicoSearch for one-way flight options from Kissimmee to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
Search for one-way flight options from Kissimmee to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Frontier deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/136:15 am -
Nonstop3h 03m
Deal found 8/27![Frontier logo]()
$84
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:36 pm -
Nonstop3h 01m
Deal found 8/31![Frontier logo]()
$85
This Cheapflightsfares deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:20 am -
Nonstop2h 55m
Deal found 8/31![Frontier logo]()
$86
This eDestinos deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Mon 9/2811:00 pm -
Nonstop2h 52m
Deal found 8/28![Frontier logo]()
$87
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:20 am -
Nonstop2h 55m
Deal found 8/31![Frontier logo]()
$88
This eDestinos deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:49 am -
1 stop13h 26m
Deal found 8/27![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop10h 12m
Deal found 8/28![JetBlue logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/911:00 pm -
Nonstop2h 50m
Deal found 8/30![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:00 am -
Nonstop2h 58m
Deal found 8/29![Frontier logo]()
$95
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:53 am -
1 stop11h 54m
Deal found 8/27![American Airlines logo]()
$96
This Super.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/116:15 am -
Nonstop3h 03m
Deal found 8/26![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/239:36 pm -
1 stop12h 37m
Deal found 8/28![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 August 31, 2026.
Round-trip from | $166 (Kiwi.com) |
|---|---|
One-way from | $84 (Frontier) |
Popular in | December |
Cheapest in | February |
Average price | $256 |
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 August 31, 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
Thu 10/29
2:50 pm-12:10 am
2 stops9h 20m
San Juan Luis Munoz Marin Intl
Sun 11/1
5:35 am-7:45 am
Nonstop3h 10m
$241
OrlandoMayagüez
MCO Orlando - MAZ Mayagüez Eugenio M De Hostos
MCOMAZ
Orlando
Fri 9/25
11:16 am-4:11 pm
1 stop4h 55m
Mayagüez Eugenio M De Hostos
Mon 9/28
7:35 am-5:59 am
1 stop22h 24m
$243
Quickest round-trip
OrlandoPonce
MCO Orlando - PSE Ponce Mercedita
MCOPSE
Orlando
Wed 9/30
5:05 am-8:01 am
Nonstop2h 56m
Ponce Mercedita
Sun 10/4
10:05 am-1:10 pm
Nonstop3h 05m
$250
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Sat 10/3
1:45 pm-10:10 pm
2 stops8h 25m
San Juan Luis Munoz Marin Intl
Wed 10/7
5:50 am-7:45 pm
2 stops13h 55m
$280
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Mon 9/28
12:45 pm-10:55 pm
2 stops10h 10m
San Juan Luis Munoz Marin Intl
Mon 10/5
5:30 am-2:05 pm
1 stop8h 35m
$280
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Thu 11/5
3:10 pm-1:05 am
1 stop8h 55m
San Juan Luis Munoz Marin Intl
Sat 11/7
6:45 am-8:30 pm
2 stops14h 45m
$280
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Thu 10/8
10:45 am-8:00 pm
1 stop9h 15m
San Juan Luis Munoz Marin Intl
Tue 10/13
5:50 am-4:35 pm
2 stops10h 45m
$280
OrlandoSan Juan
MCO Orlando - SJU San Juan Luis Munoz Marin Intl
MCOSJU
Orlando
Sat 9/26
1:10 pm-10:00 pm
2 stops8h 50m
San Juan Luis Munoz Marin Intl
Sat 10/3
5:40 am-1:50 pm
1 stop8h 10m
$280
OrlandoPonce
MCO Orlando - PSE Ponce Mercedita
MCOPSE
Orlando
Sat 9/19
5:05 am-8:01 am
Nonstop2h 56m
Ponce Mercedita
Sat 9/26
8:55 am-12:01 pm
Nonstop3h 06m
$283
OrlandoPonce
MCO Orlando - PSE Ponce Mercedita
MCOPSE
Orlando
Wed 10/28
5:30 am-8:22 am
Nonstop2h 52m
Ponce Mercedita
Sun 11/1
10:12 am-12:27 pm
Nonstop3h 15m
$283
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-MAZ
MCO-PSE
MCO-BQN
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-MAZ
MCO-PSE
MCO-BQN
What is the cheapest time of day to fly from K1S to PR?
Find hourly flight availability from Kissimmee to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 31, 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 August 31, 2026.
The most flights from K1S to PR0 are scheduled on a Friday (32 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (13 on average).
What is the cheapest day to fly from Kissimmee to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Puerto Rico. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Kissimmee to Puerto Rico flight should consider departing on Sunday afternoons when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated August 31, 2026.
Read through reviews of airlines operating flights from Kissimmee to Puerto Rico, such as Southwest,American Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Kissimmee to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Kissimmee to Puerto Rico
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Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kissimmee to Puerto Rico by cabin class
Find flights from Kissimmee to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kissimmee and Puerto Rico flights
Browse other Kissimmee and Puerto Rico flight options. Last updated on August 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Kissimmee to Puerto Rico
Discover the top 5 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 August 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$111 | Average$273 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$283 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$365 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$226 | Average$379 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$369 | FlexibilityNo cancel fee | On-time63% |