$173+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Sep 15 — Sep 221
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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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 August 16, 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 August 16, 2026.
This Delta deal was found by Cheapflights users on 8/14. 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.
Sun 9/61:45 pm -
1 stop7h 44m
Wed 9/162:59 pm -
1 stop8h 42m
Deal found 8/14![Delta logo]()
$316
This Delta deal was found by Cheapflights users on 8/12. 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.
Fri 9/115:50 am -
1 stop9h 59m
Fri 9/1812:56 pm -
1 stop10h 45m
Deal found 8/12![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Wed 10/2810:46 am -
2 stops11h 50m
Sat 10/311:35 pm -
2 stops10h 27m
Deal found 8/13![United Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Sun 9/612:38 pm -
2 stops10h 37m
Wed 9/1611:51 am -
2 stops11h 19m
Deal found 8/11![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Wed 9/304:23 pm -
2 stops17h 37m
Mon 10/52:54 pm -
1 stop10h 18m
Deal found 8/11![American Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Thu 9/106:30 am -
2 stops13h 08m
Wed 9/161:00 am -
2 stops9h 40m
Deal found 8/13![United Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Thu 10/86:00 am -
1 stop15h 57m
Mon 10/122:54 pm -
1 stop18h 17m
Deal found 8/11![American Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:55 pm -
1 stop11h 16m
Tue 9/86:35 am -
2 stops28h 18m
Deal found 8/12![Multiple Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Wed 10/287:14 am -
1 stop6h 47m
Sat 10/312:54 pm -
1 stop10h 18m
Deal found 8/12![American Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Wed 9/3010:33 am -
1 stop12h 25m
Mon 10/510:42 am -
1 stop28h 23m
Deal found 8/14![Multiple Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 8/13. 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 10/178:10 am -
2 stops13h 59m
Tue 10/2012:15 am -
2 stops12h 38m
Deal found 8/13![United Airlines logo]()
$446
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:05 am -
2 stops14h 04m
Tue 9/1512:15 am -
2 stops14h 27m
Deal found 8/10![United Airlines logo]()
$576
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 August 16, 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 August 16, 2026.
This Delta deal was found by Cheapflights users on 8/13. 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 9/61:45 pm -
1 stop7h 44m
Wed 9/162:59 pm -
1 stop8h 42m
Deal found 8/13![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Tue 9/86:00 am -
1 stop15h 24m
Fri 9/183:35 pm -
1 stop8h 22m
Deal found 8/13![American Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Thu 9/106:30 am -
2 stops13h 08m
Wed 9/161:00 am -
2 stops9h 40m
Deal found 8/13![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 9/115:50 am -
1 stop9h 59m
Fri 9/1812:56 pm -
1 stop10h 45m
Deal found 8/13![Delta logo]()
$341
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:00 am -
1 stop8h 44m
Sat 10/31:25 pm -
1 stop7h 50m
Deal found 8/10![United Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Wed 9/302:17 pm -
2 stops18h 07m
Mon 10/512:41 pm -
2 stops12h 31m
Deal found 8/11![American Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 8/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/106:15 am -
1 stop7h 55m
Thu 1/143:20 pm -
1 stop9h 35m
Deal found 8/11![Delta logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 10/246:42 am -
2 stops12h 56m
Wed 10/283:55 pm -
1 stop8h 12m
Deal found 8/14![United Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 8/12. 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 10/178:10 am -
2 stops13h 59m
Tue 10/2012:15 am -
2 stops12h 38m
Deal found 8/12![United Airlines logo]()
$446
This United Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 1/102:50 pm -
2 stops13h 21m
Wed 1/132:05 am -
2 stops13h 45m
Deal found 8/15![United Airlines logo]()
$471
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:05 am -
2 stops14h 04m
Tue 9/1512:15 am -
2 stops14h 27m
Deal found 8/10![United Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 8/13. 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 1/98:20 am -
2 stops13h 37m
Thu 1/141:09 am -
2 stops10h 35m
Deal found 8/13![United Airlines logo]()
$581
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Mon 10/2610:46 am -
2 stops28h 25m
Fri 10/301:25 pm -
2 stops10h 37m
Deal found 8/12![United Airlines logo]()
$1,226
This United Airlines deal was found by Cheapflights users on 8/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:00 am -
2 stops11h 21m
Sat 10/310:48 am -
2 stops10h 27m
Deal found 8/11![United Airlines logo]()
$2,277
Last-minute flights from Madison to Puerto RicoDiscover last-minute flight deals from Madison to Puerto Rico. Data last updated August 16, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Puerto Rico. Data last updated August 16, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Fri 9/47:47 am -
1 stop14h 28m
Tue 9/87:30 am -
1 stop16h 39m
Deal found 8/10![American Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:55 pm -
1 stop11h 16m
Tue 9/86:35 am -
2 stops28h 18m
Deal found 8/12![Multiple Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 8/14. 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.
Sun 9/61:45 pm -
1 stop7h 44m
Wed 9/162:59 pm -
1 stop8h 42m
Deal found 8/14![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Sun 9/612:38 pm -
2 stops10h 37m
Wed 9/1611:51 am -
2 stops11h 19m
Deal found 8/11![American Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Thu 9/106:30 am -
2 stops13h 08m
Wed 9/161:00 am -
2 stops9h 40m
Deal found 8/13![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 8/12. 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.
Fri 9/115:50 am -
1 stop9h 59m
Fri 9/1812:56 pm -
1 stop10h 45m
Deal found 8/12![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:05 am -
2 stops14h 04m
Tue 9/1512:15 am -
2 stops14h 27m
Deal found 8/10![United Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 8/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:00 am -
2 stops11h 21m
Sat 10/310:48 am -
2 stops10h 27m
Deal found 8/11![United Airlines logo]()
$2,277
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Wed 9/304:23 pm -
2 stops17h 37m
Mon 10/52:54 pm -
1 stop10h 18m
Deal found 8/11![American Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Wed 9/3010:33 am -
1 stop12h 25m
Mon 10/510:42 am -
1 stop28h 23m
Deal found 8/14![Multiple Airlines logo]()
$400
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 August 16, 2026.
Search for one-way flight options from Madison to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 16, 2026.
This American Airlines deal was found by Cheapflights users on 8/12. 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 10/187:05 pm -
1 stop17h 58m
Deal found 8/12![American Airlines logo]()
$173
This United Airlines deal was found by Cheapflights users on 8/12. 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 10/1712:39 pm -
2 stops10h 11m
Deal found 8/12![United Airlines logo]()
$183
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Wed 12/910:40 am -
1 stop8h 20m
Deal found 8/12![United Airlines logo]()
$213
This United Airlines deal was found by Cheapflights users on 8/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/165:40 pm -
2 stops10h 31m
Deal found 8/11![United Airlines logo]()
$218
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 1/165:00 am -
1 stop14h 39m
Deal found 8/14![American Airlines logo]()
$233
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Wed 12/97:10 am -
2 stops12h 28m
Deal found 8/12![American Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:33 am -
3 stops38h 36m
Deal found 8/12![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 pm -
1 stop14h 57m
Deal found 8/12![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 pm -
2 stops21h 06m
Deal found 8/12![Multiple Airlines logo]()
$262
This American Airlines deal was found by Cheapflights users on 8/11. 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 11/276:38 pm -
1 stop16h 54m
Deal found 8/11![American Airlines logo]()
$284
This United Airlines deal was found by Cheapflights users on 8/12. 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 10/188:10 am -
2 stops13h 59m
Deal found 8/12![United Airlines logo]()
$458
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 August 16, 2026.
Round-trip from | $316 (Delta) |
|---|---|
One-way from | $173 (American Airlines) |
Popular in | April |
Cheapest in | September |
Average price | $366 |
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 August 16, 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 Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Sun 9/6
1:45 pm-10:29 pm
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Wed 9/16
2:59 pm-10:41 pm
1 stop8h 42m
$316
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Fri 9/11
5:50 am-4:49 pm
1 stop9h 59m
San Juan Luis Munoz Marin Intl
Fri 9/18
12:56 pm-10:41 pm
1 stop10h 45m
$341
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Tue 9/8
6:00 am-10:24 pm
1 stop15h 24m
San Juan Luis Munoz Marin Intl
Fri 9/18
3:35 pm-10:57 pm
1 stop8h 22m
$366
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Thu 9/10
6:30 am-8:38 pm
2 stops13h 08m
San Juan Luis Munoz Marin Intl
Wed 9/16
1:00 am-9:40 am
2 stops9h 40m
$373
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Sun 1/10
6:15 am-4:10 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Thu 1/14
3:20 pm-10:55 pm
1 stop9h 35m
$391
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Tue 9/29
5:00 am-2:44 pm
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Sat 10/3
1:25 pm-8:15 pm
1 stop7h 50m
$411
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Wed 9/30
2:17 pm-9:24 am
2 stops18h 07m
San Juan Luis Munoz Marin Intl
Mon 10/5
12:41 pm-12:12 am
2 stops12h 31m
$416
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Sat 10/24
6:42 am-8:38 pm
2 stops12h 56m
San Juan Luis Munoz Marin Intl
Wed 10/28
3:55 pm-11:07 pm
1 stop8h 12m
$431
MadisonAguadilla
MSN Madison Truax Field - BQN Aguadilla Borinquen
MSNBQN
Madison Truax Field
Sat 10/17
8:10 am-11:09 pm
2 stops13h 59m
Aguadilla Borinquen
Tue 10/20
12:15 am-11:53 am
2 stops12h 38m
$446
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Sun 1/10
2:50 pm-6:11 am
2 stops13h 21m
San Juan Luis Munoz Marin Intl
Wed 1/13
2:05 am-1:50 pm
2 stops13h 45m
$471
Showing 1-10 of 23 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-CPX
MSN-MAZ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Madison to Puerto Rico
MSN-PR0
MSN-SJU
MSN-BQN
MSN-CPX
MSN-MAZ
What is the cheapest month to book a flight from Madison to Puerto Rico?
Currently, September is the cheapest month in which you can book a flight from Madison to Puerto Rico (average of $345). Flying from Madison to Puerto Rico in April is currently the most expensive (average of $676). 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 36 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 August 16, 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.
Boarding
8.1
Overall
7.8
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Overall
7.8
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Overall
7.8
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Overall
7.8
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
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
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
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Madison and Puerto Rico flights
Browse other Madison and Puerto Rico flight options. Last updated on August 16, 2026.
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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 August 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$226 | Average$502 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$246 | Average$531 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$295 | Average$584 | FlexibilityNo cancel fee | On-time71% |