$133+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Aug 1 — Aug 81
Round-trip
1 adult, Economy
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Find cheap flights from Madison 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
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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 July 2, 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 July 2, 2026.
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:43 am
MSN
- SJU
1 stop6h 59m
Delta
Tue 9/12:59 pm
SJU
- MSN
1 stop8h 39m
Delta
Deal found 6/30![Delta logo]()
$266
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/236:30 am
MSN
- SJU
1 stop7h 14m
United Airlines
Fri 8/287:00 am
SJU
- MSN
2 stops14h 53m
United Airlines
Deal found 7/1![United Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:27 am
MSN
- SJU
1 stop13h 29m
Multiple Airlines
Tue 9/15:37 pm
SJU
- MSN
1 stop17h 10m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 6/28. 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.
Sun 9/66:30 am
MSN
- SJU
1 stop7h 14m
United Airlines
Tue 9/151:00 am
SJU
- MSN
1 stop10h 14m
United Airlines
Deal found 6/28![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:43 am
MSN
- SJU
1 stop9h 55m
Delta
Thu 9/37:00 am
SJU
- MSN
1 stop10h 20m
Delta
Deal found 6/30![Delta logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Sat 8/2210:27 am
MSN
- SJU
1 stop13h 29m
Multiple Airlines
Tue 8/255:37 pm
SJU
- MSN
1 stop17h 10m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:43 am
MSN
- SJU
1 stop9h 55m
Delta
Wed 9/162:59 pm
SJU
- MSN
1 stop8h 54m
Delta
Deal found 6/30![Delta logo]()
$323
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:53 am
MSN
- SJU
1 stop10h 50m
American Airlines
Tue 8/257:30 am
SJU
- MSN
1 stop16h 39m
American Airlines
Deal found 6/28![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Wed 8/195:00 am
MSN
- SJU
1 stop17h 15m
American Airlines
Wed 8/267:30 am
SJU
- MSN
1 stop16h 39m
American Airlines
Deal found 6/27![American Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Sun 11/110:40 am
MSN
- SJU
1 stop8h 20m
United Airlines
Sat 11/78:05 am
SJU
- MSN
2 stops10h 57m
United Airlines
Deal found 6/30![United Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 10/38:10 am
MSN
- BQN
2 stops13h 59m
United Airlines
Tue 10/612:15 am
BQN
- MSN
2 stops12h 38m
United Airlines
Deal found 7/1![United Airlines logo]()
$396
This United Airlines deal was found by Cheapflights users on 6/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:05 am
MSN
- BQN
2 stops14h 04m
United Airlines
Sat 9/2612:15 am
BQN
- MSN
2 stops12h 38m
United Airlines
Deal found 6/27![United Airlines logo]()
$472
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 July 2, 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 July 2, 2026.
This United Airlines deal was found by Cheapflights users on 6/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2210:46 am
MSN
- SJU
2 stops12h 04m
United Airlines
Fri 9/253:56 pm
SJU
- MSN
1 stop7h 39m
United Airlines
Deal found 6/27![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 6/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:33 am
MSN
- SJU
1 stop9h 46m
Delta
Fri 9/252:59 pm
SJU
- MSN
1 stop8h 54m
Delta
Deal found 6/27![Delta logo]()
$266
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 7/286:00 am
MSN
- SJU
2 stops11h 24m
American Airlines
Sun 8/212:59 am
SJU
- MSN
1 stop9h 12m
American Airlines
Deal found 7/1![American Airlines logo]()
$389
This United Airlines deal was found by Cheapflights users on 6/28. 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.
Sun 9/68:10 am
MSN
- SJU
2 stops11h 28m
United Airlines
Tue 9/151:00 am
SJU
- MSN
2 stops9h 41m
United Airlines
Deal found 6/28![United Airlines logo]()
$281
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/236:30 am
MSN
- SJU
1 stop7h 14m
United Airlines
Fri 8/287:00 am
SJU
- MSN
2 stops14h 53m
United Airlines
Deal found 7/1![United Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:43 am
MSN
- SJU
1 stop9h 55m
Delta
Wed 9/162:59 pm
SJU
- MSN
1 stop8h 54m
Delta
Deal found 6/29![Delta logo]()
$323
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:45 pm
MSN
- SJU
1 stop7h 44m
Delta
Wed 9/27:30 am
SJU
- MSN
2 stops14h 49m
Delta
Deal found 6/30![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Thu 10/86:00 am
MSN
- SJU
1 stop16h 41m
American Airlines
Mon 10/122:25 pm
SJU
- MSN
1 stop9h 53m
American Airlines
Deal found 6/27![American Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 6/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:05 am
MSN
- BQN
2 stops14h 04m
United Airlines
Sat 9/2612:15 am
BQN
- MSN
2 stops12h 38m
United Airlines
Deal found 6/27![United Airlines logo]()
$472
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Sat 10/36:06 am
MSN
- BQN
1 stop16h 03m
United Airlines
Tue 10/612:15 am
BQN
- MSN
2 stops14h 22m
United Airlines
Deal found 6/29![United Airlines logo]()
$546
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 12/510:40 am
MSN
- SJU
2 stops9h 42m
United Airlines
Mon 12/148:30 am
SJU
- MSN
2 stops12h 32m
United Airlines
Deal found 7/1![United Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 11/135:00 am
MSN
- SJU
1 stop8h 40m
United Airlines
Sat 11/212:05 am
SJU
- MSN
2 stops13h 45m
United Airlines
Deal found 6/30![United Airlines logo]()
$611
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Tue 8/2510:57 am
MSN
- MAZ
2 stops28h 14m
United Airlines
Fri 8/281:19 pm
MAZ
- MSN
2 stops10h 32m
United Airlines
Deal found 6/30![United Airlines logo]()
$1,488
Last-minute flights from Madison to Puerto RicoDiscover last-minute flight deals from Madison to Puerto Rico. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Puerto Rico. Data last updated July 2, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/28. 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.
Thu 7/25:00 am
MSN
- BQN
2 stops17h 09m
United Airlines
Wed 7/812:15 am
BQN
- MSN
2 stops12h 34m
United Airlines
Deal found 6/28![United Airlines logo]()
$770
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Wed 8/195:00 am
MSN
- SJU
1 stop17h 15m
American Airlines
Wed 8/267:30 am
SJU
- MSN
1 stop16h 39m
American Airlines
Deal found 6/27![American Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Wed 8/1910:27 am
MSN
- SJU
1 stop13h 29m
Multiple Airlines
Tue 8/255:37 pm
SJU
- MSN
1 stop17h 10m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Sat 8/2210:27 am
MSN
- SJU
1 stop13h 29m
Multiple Airlines
Tue 8/255:37 pm
SJU
- MSN
1 stop17h 10m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:53 am
MSN
- SJU
1 stop10h 50m
American Airlines
Tue 8/257:30 am
SJU
- MSN
1 stop16h 39m
American Airlines
Deal found 6/30![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/236:30 am
MSN
- SJU
1 stop7h 14m
United Airlines
Fri 8/287:00 am
SJU
- MSN
2 stops14h 53m
United Airlines
Deal found 7/1![United Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:27 am
MSN
- SJU
1 stop13h 29m
Multiple Airlines
Tue 9/15:37 pm
SJU
- MSN
1 stop17h 10m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:03 am
MSN
- SJU
2 stops14h 26m
Delta
Tue 9/112:56 pm
SJU
- MSN
1 stop10h 42m
Delta
Deal found 6/30![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:43 am
MSN
- SJU
1 stop6h 59m
Delta
Thu 9/37:00 am
SJU
- MSN
2 stops11h 35m
Delta
Deal found 6/30![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:43 am
MSN
- SJU
1 stop6h 59m
Delta
Tue 9/12:59 pm
SJU
- MSN
1 stop8h 39m
Delta
Deal found 6/30![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am
MSN
- SJU
2 stops15h 24m
Delta
Thu 9/37:00 am
SJU
- MSN
1 stop10h 20m
Delta
Deal found 6/30![Delta logo]()
$296
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:00 am
MSN
- SJU
2 stops11h 33m
American Airlines
Fri 9/47:30 am
SJU
- MSN
1 stop16h 39m
American Airlines
Deal found 6/30![American Airlines logo]()
$351
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 July 2, 2026.
Search for one-way flight options from Madison to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/89:32 am
MSN
- SJU
2 stops11h 47m
Delta
Deal found 7/1![Delta logo]()
$133
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Sat 10/175:00 am
MSN
- SJU
1 stop8h 44m
United Airlines
Deal found 6/30![United Airlines logo]()
$163
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Tue 7/2812:30 pm
MSN
- BQN
2 stops9h 39m
United Airlines
Deal found 6/30![United Airlines logo]()
$183
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:30 am
MSN
- SJU
2 stops14h 25m
American Airlines
Deal found 6/30![American Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 10/177:00 am
MSN
- SJU
2 stops14h 22m
American Airlines
Deal found 7/1![American Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:27 am
MSN
- SJU
1 stop13h 14m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$276
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/88:05 am
MSN
- BQN
2 stops14h 04m
United Airlines
Deal found 7/1![United Airlines logo]()
$276
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am
MSN
- SJU
1 stop15h 57m
American Airlines
Deal found 6/29![American Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:00 am
MSN
- SJU
2 stops11h 24m
American Airlines
Deal found 6/28![American Airlines logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:05 pm
MSN
- BQN
1 stop15h 59m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:50 pm
MSN
- SJU
3 stops28h 51m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Thu 10/156:00 pm
MSN
- SJU
2 stops20h 19m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$312
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 July 2, 2026.
Round-trip from | $266 (Delta) |
|---|---|
One-way from | $133 (Delta) |
Popular in | April |
Cheapest in | September |
Average price | $586 |
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 July 2, 2026.
Use the filters below to find and compare flights from Madison to Puerto Rico that are best for you.
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Cheapest round-trip
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Tue 9/22
10:46 am-11:50 pm
2 stops12h 04m
San Juan Luis Munoz Marin Intl
Fri 9/25
3:56 pm-10:35 pm
1 stop7h 39m
$266
Quickest round-trip
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Tue 9/22
11:33 am-10:19 pm
1 stop9h 46m
San Juan Luis Munoz Marin Intl
Fri 9/25
2:59 pm-10:53 pm
1 stop8h 54m
$266
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sun 9/6
8:10 am-8:38 pm
2 stops11h 28m
San Juan Luis Munoz Marin Intl
Tue 9/15
1:00 am-9:41 am
2 stops9h 41m
$281
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sun 8/23
6:30 am-2:44 pm
1 stop7h 14m
San Juan Luis Munoz Marin Intl
Fri 8/28
7:00 am-8:53 pm
2 stops14h 53m
$281
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sun 9/6
5:43 am-4:38 pm
1 stop9h 55m
San Juan Luis Munoz Marin Intl
Wed 9/16
2:59 pm-10:53 pm
1 stop8h 54m
$323
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sat 8/29
1:45 pm-10:29 pm
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Wed 9/2
7:30 am-9:19 pm
2 stops14h 49m
$326
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Tue 7/28
6:00 am-6:24 pm
2 stops11h 24m
San Juan Luis Munoz Marin Intl
Sun 8/2
12:59 am-9:11 am
1 stop9h 12m
$389
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Thu 10/8
6:00 am-11:41 pm
1 stop16h 41m
San Juan Luis Munoz Marin Intl
Mon 10/12
2:25 pm-11:18 pm
1 stop9h 53m
$429
MadisonAguadilla
MSN - BQN
MSNBQN
Madison Truax Field
Sat 9/19
8:05 am-11:09 pm
2 stops14h 04m
Aguadilla Borinquen
Sat 9/26
12:15 am-11:53 am
2 stops12h 38m
$472
MadisonAguadilla
MSN - BQN
MSNBQN
Madison Truax Field
Sat 10/3
6:06 am-11:09 pm
1 stop16h 03m
Aguadilla Borinquen
Tue 10/6
12:15 am-1:37 pm
2 stops14h 22m
$546
Showing 1-10 of 24 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
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 $418). 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.
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.
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 July 2, 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.
Crew
8.5
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
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
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 Madison to Puerto Rico by cabin class
Find flights from Madison to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Madison and Puerto Rico flights
Browse other Madison and Puerto Rico flight options. Last updated on July 2, 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 July 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$225 | Average$531 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$512 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$265 | Average$563 | FlexibilityNo cancel fee | On-time71% |