$163+ Cheap flights from Madison (MSN) 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Jun 14 — Jun 211
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Puerto Rico with Cheapflights
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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
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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 Madison to Puerto Rico
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Cheapest flights from Madison to Puerto RicoExplore the most affordable flight options available from Madison to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.
Explore the most affordable flight options available from Madison to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:00 am
MSN
- SJU
2 stops14h 00m
Delta
Tue 9/297:00 am
SJU
- MSN
2 stops14h 40m
Delta
Deal found 5/13![Delta logo]()
$246
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:30 am
MSN
- SJU
2 stops13h 08m
United Airlines
Tue 9/151:00 am
SJU
- MSN
2 stops9h 44m
United Airlines
Deal found 5/13![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:00 am
MSN
- SJU
2 stops14h 00m
Delta
Sat 9/267:00 am
SJU
- MSN
2 stops14h 40m
Delta
Deal found 5/13![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:00 am
MSN
- SJU
2 stops14h 23m
Delta
Wed 9/167:00 am
SJU
- MSN
2 stops14h 40m
Delta
Deal found 5/13![Delta logo]()
$286
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:30 am
MSN
- SJU
2 stops13h 08m
United Airlines
Fri 9/251:00 am
SJU
- MSN
2 stops9h 53m
United Airlines
Deal found 5/13![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:45 am
MSN
- SJU
1 stop9h 46m
Delta
Sat 9/267:00 am
SJU
- MSN
2 stops14h 40m
Delta
Deal found 5/13![Delta logo]()
$321
This American Airlines deal was found by Cheapflights users on 5/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:19 am
MSN
- SJU
1 stop15h 31m
American Airlines
Wed 10/288:30 am
SJU
- MSN
2 stops11h 26m
American Airlines
Deal found 5/12![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:00 am
MSN
- SJU
2 stops14h 38m
United Airlines
Tue 9/221:00 am
SJU
- MSN
2 stops13h 43m
United Airlines
Deal found 5/13![United Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 5/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/612:40 pm
MSN
- SJU
2 stops10h 35m
American Airlines
Wed 9/162:05 pm
SJU
- MSN
2 stops11h 16m
American Airlines
Deal found 5/12![American Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Sat 8/2210:27 am
MSN
- SJU
1 stop12h 56m
Multiple Airlines
Thu 8/278:00 am
SJU
- MSN
1 stop25h 25m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:15 am
MSN
- BQN
2 stops14h 54m
United Airlines
Wed 9/912:15 am
BQN
- MSN
2 stops10h 29m
United Airlines
Deal found 5/12![United Airlines logo]()
$528
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:30 am
MSN
- BQN
2 stops15h 39m
United Airlines
Wed 8/2612:15 am
BQN
- MSN
2 stops14h 27m
United Airlines
Deal found 5/14![United Airlines logo]()
$591
Best flights from Madison to Puerto RicoDiscover carefully curated flight deals from Madison to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 15, 2026.
Discover carefully curated flight deals from Madison to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 15, 2026.
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
MSN
- SJU
2 stops9h 46m
Delta
Tue 7/72:21 pm
SJU
- MSN
1 stop7h 38m
Delta
Deal found 5/14![Delta logo]()
$418
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:15 am
MSN
- BQN
2 stops14h 54m
United Airlines
Wed 9/912:15 am
BQN
- MSN
2 stops10h 29m
United Airlines
Deal found 5/13![United Airlines logo]()
$528
This American Airlines deal was found by Cheapflights users on 5/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:41 am
MSN
- SJU
1 stop14h 07m
American Airlines
Sat 8/112:59 am
SJU
- MSN
1 stop7h 52m
American Airlines
Deal found 5/11![American Airlines logo]()
$572
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Fri 6/126:50 pm
MSN
- SJU
2 stops28h 47m
Multiple Airlines
Tue 6/165:15 pm
SJU
- MSN
1 stop16h 59m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$584
This Delta deal was found by Cheapflights users on 5/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:00 am
MSN
- SJU
2 stops15h 29m
Delta
Fri 8/2812:56 pm
SJU
- MSN
1 stop10h 36m
Delta
Deal found 5/9![Delta logo]()
$506
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:30 am
MSN
- BQN
2 stops15h 39m
United Airlines
Wed 8/2612:15 am
BQN
- MSN
2 stops14h 27m
United Airlines
Deal found 5/14![United Airlines logo]()
$591
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:01 am
MSN
- SJU
2 stops11h 24m
American Airlines
Tue 6/1610:29 am
SJU
- MSN
2 stops11h 51m
American Airlines
Deal found 5/13![American Airlines logo]()
$654
This Delta deal was found by Cheapflights users on 5/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/29:32 am
MSN
- SJU
2 stops13h 21m
Delta
Tue 9/17:00 am
SJU
- MSN
2 stops14h 40m
Delta
Deal found 5/9![Delta logo]()
$601
This Delta deal was found by Cheapflights users on 5/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/305:48 am
MSN
- SJU
1 stop9h 57m
Delta
Sun 8/3012:56 pm
SJU
- MSN
1 stop10h 36m
Delta
Deal found 5/9![Delta logo]()
$708
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:10 am
MSN
- BQN
2 stops13h 59m
United Airlines
Mon 6/112:15 am
BQN
- MSN
2 stops10h 44m
United Airlines
Deal found 5/14![United Airlines logo]()
$856
This Delta deal was found by Cheapflights users on 5/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/319:32 am
MSN
- SJU
2 stops11h 57m
Delta
Wed 9/27:00 am
SJU
- MSN
2 stops14h 40m
Delta
Deal found 5/9![Delta logo]()
$708
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:00 am
MSN
- SJU
2 stops13h 45m
Delta
Fri 7/3112:56 pm
SJU
- MSN
1 stop10h 42m
Delta
Deal found 5/12![Delta logo]()
$786
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:05 am
MSN
- MAZ
2 stops31h 44m
United Airlines
Wed 8/261:25 pm
MAZ
- MSN
2 stops10h 26m
United Airlines
Deal found 5/14![United Airlines logo]()
$1,735
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:40 am
MSN
- MAZ
2 stops31h 09m
United Airlines
Wed 9/21:25 pm
MAZ
- MSN
2 stops21h 48m
United Airlines
Deal found 5/12![United Airlines logo]()
$1,885
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:30 am
MSN
- CPX
2 stops9h 51m
United Airlines
Fri 6/510:48 am
CPX
- MSN
2 stops10h 51m
United Airlines
Deal found 5/13![United Airlines logo]()
$2,130
Last-minute flights from Madison to Puerto RicoDiscover last-minute flight deals from Madison to Puerto Rico. Data last updated May 15, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Puerto Rico. Data last updated May 15, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:45 am
MSN
- SJU
2 stops13h 39m
American Airlines
Thu 5/217:00 am
SJU
- MSN
1 stop9h 53m
American Airlines
Deal found 5/13![American Airlines logo]()
$560
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:04 am
MSN
- SJU
1 stop10h 13m
Delta
Sat 5/237:30 am
SJU
- MSN
2 stops14h 57m
Delta
Deal found 5/13![Delta logo]()
$510
This American Airlines deal was found by Cheapflights users on 5/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:45 am
MSN
- SJU
2 stops13h 39m
American Airlines
Sat 5/237:00 am
SJU
- MSN
2 stops11h 22m
American Airlines
Deal found 5/11![American Airlines logo]()
$550
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/241:25 pm
MSN
- SJU
1 stop8h 36m
American Airlines
Thu 5/286:00 am
SJU
- MSN
2 stops11h 31m
American Airlines
Deal found 5/13![American Airlines logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Mon 5/256:50 pm
MSN
- SJU
1 stop21h 22m
Multiple Airlines
Thu 5/289:00 am
SJU
- MSN
1 stop24h 25m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Wed 5/276:05 pm
MSN
- SJU
2 stops28h 54m
Multiple Airlines
Fri 5/294:46 pm
SJU
- MSN
1 stop17h 28m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$480
This American Airlines deal was found by Cheapflights users on 5/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:00 am
MSN
- SJU
1 stop14h 45m
American Airlines
Fri 6/57:00 am
SJU
- MSN
1 stop17h 59m
American Airlines
Deal found 5/11![American Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 5/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:02 am
MSN
- SJU
2 stops11h 23m
American Airlines
Wed 6/106:21 am
SJU
- MSN
1 stop12h 01m
American Airlines
Deal found 5/12![American Airlines logo]()
$552
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:10 am
MSN
- BQN
2 stops13h 59m
United Airlines
Mon 6/112:15 am
BQN
- MSN
2 stops10h 44m
United Airlines
Deal found 5/14![United Airlines logo]()
$856
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:02 am
MSN
- SJU
2 stops11h 23m
American Airlines
Tue 6/97:00 am
SJU
- MSN
1 stop18h 09m
American Airlines
Deal found 5/13![American Airlines logo]()
$511
This American Airlines deal was found by Cheapflights users on 5/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:02 am
MSN
- SJU
1 stop15h 59m
American Airlines
Sun 6/147:00 am
SJU
- MSN
1 stop17h 59m
American Airlines
Deal found 5/10![American Airlines logo]()
$561
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:30 am
MSN
- CPX
2 stops9h 51m
United Airlines
Fri 6/510:48 am
CPX
- MSN
2 stops10h 51m
United Airlines
Deal found 5/13![United Airlines logo]()
$2,130
One-way flights from Madison to Puerto RicoSearch for one-way flight options from Madison to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
Search for one-way flight options from Madison to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:43 am
MSN
- SJU
1 stop9h 54m
Delta
Deal found 5/13![Delta logo]()
$163
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:38 am
MSN
- SJU
1 stop16h 21m
American Airlines
Deal found 5/14![American Airlines logo]()
$172
This American Airlines deal was found by Cheapflights users on 5/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
MSN
- SJU
2 stops11h 24m
American Airlines
Deal found 5/11![American Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Wed 5/276:05 pm
MSN
- SJU
2 stops46h 09m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 5/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:01 am
MSN
- SJU
1 stop15h 59m
American Airlines
Deal found 5/11![American Airlines logo]()
$246
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:30 am
MSN
- SJU
2 stops13h 00m
Delta
Deal found 5/13![Delta logo]()
$255
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:50 am
MSN
- SJU
1 stop10h 13m
American Airlines
Deal found 5/13![American Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:50 pm
MSN
- SJU
1 stop21h 22m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:55 pm
MSN
- BQN
1 stop14h 36m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:55 pm
MSN
- BQN
1 stop14h 38m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:50 pm
MSN
- BQN
2 stops39h 41m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:05 pm
MSN
- BQN
1 stop16h 26m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$364
Find flight deals from Madison to Puerto Rico
Keep the following information in mind while searching for Madison to Puerto Rico flight deals. Data was last updated May 15, 2026.
Round-trip from | $246 (Delta) |
|---|---|
One-way from | $163 (Delta) |
Popular in | April |
Cheapest in | September |
Average price | $415 |
Cheapflights Fare Finder
Customize your flight search to find flights from Madison 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 May 15, 2026.
Use the filters below to find and compare flights from Madison to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sat 7/4
6:00 am-4:46 pm
2 stops9h 46m
San Juan Luis Munoz Marin Intl
Tue 7/7
2:21 pm-8:59 pm
1 stop7h 38m
$418
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Thu 7/30
6:00 am-10:29 pm
2 stops15h 29m
San Juan Luis Munoz Marin Intl
Fri 8/28
12:56 pm-10:32 pm
1 stop10h 36m
$506
MadisonAguadilla
MSN - BQN
MSNBQN
Madison Truax Field
Sun 9/6
7:15 am-11:09 pm
2 stops14h 54m
Aguadilla Borinquen
Wed 9/9
12:15 am-9:44 am
2 stops10h 29m
$528
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sat 7/25
8:41 am-11:48 pm
1 stop14h 07m
San Juan Luis Munoz Marin Intl
Sat 8/1
12:59 am-7:51 am
1 stop7h 52m
$572
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Fri 6/12
6:50 pm-12:37 am
2 stops28h 47m
San Juan Luis Munoz Marin Intl
Tue 6/16
5:15 pm-9:14 am
1 stop16h 59m
$584
MadisonAguadilla
MSN - BQN
MSNBQN
Madison Truax Field
Mon 8/24
6:30 am-11:09 pm
2 stops15h 39m
Aguadilla Borinquen
Wed 8/26
12:15 am-1:42 pm
2 stops14h 27m
$591
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sun 8/2
9:32 am-11:53 pm
2 stops13h 21m
San Juan Luis Munoz Marin Intl
Tue 9/1
7:00 am-8:40 pm
2 stops14h 40m
$601
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Fri 6/12
6:01 am-6:25 pm
2 stops11h 24m
San Juan Luis Munoz Marin Intl
Tue 6/16
10:29 am-9:20 pm
2 stops11h 51m
$654
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Thu 7/30
5:48 am-4:45 pm
1 stop9h 57m
San Juan Luis Munoz Marin Intl
Sun 8/30
12:56 pm-10:32 pm
1 stop10h 36m
$708
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Fri 7/31
9:32 am-10:29 pm
2 stops11h 57m
San Juan Luis Munoz Marin Intl
Wed 9/2
7:00 am-8:40 pm
2 stops14h 40m
$708
Showing 1-10 of 26 resultsSorted by cheapest first
Best time to book a flight from Madison to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Madison with our price prediction graph.
MSN-SJU
MSN-BQN
MSN-MAZ
MSN-CPX
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Madison to Puerto Rico
MSN-PR0
MSN-SJU
MSN-BQN
MSN-MAZ
MSN-CPX
How far ahead should I book a flight from Madison to Puerto Rico?
The price you pay for your flight from Madison to Puerto Rico may vary depending on when you book. For the best chance of a lower fare, look to book 37 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Madison to Puerto Rico?
Currently, March is the cheapest month in which you can book a flight from Madison to Puerto Rico (average of $163). Flying from Madison to Puerto Rico in July is currently the most expensive (average of $405). 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.
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 May 15, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican Airlines from Madison to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Madison 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 Madison to Puerto Rico
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Complete your trip
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Madison and Puerto Rico flights
Browse other Madison and Puerto Rico flight options. Last updated on May 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Madison to Puerto Rico
Discover the top 3 airlines that operate flights from Madison 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 May 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$225 | Average$531 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$226 | Average$495 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$268 | Average$533 | FlexibilityNo cancel fee | On-time71% |