$178+ Cheap flights from Madison (MSN) to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Oct 11 — Oct 181
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 September 11, 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 September 11, 2026.
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
1 stop8h 40m
Wed 11/47:40 am -
2 stops13h 27m
Deal found 9/8![United Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:10 am -
2 stops11h 28m
Sat 10/31:25 pm -
2 stops10h 10m
Deal found 9/9![United Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:00 am -
2 stops11h 05m
Sat 11/148:30 am -
1 stop10h 23m
Deal found 9/10![American Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/75:00 am -
1 stop8h 44m
Mon 10/121:00 am -
1 stop10h 29m
Deal found 9/6![United Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:06 pm -
2 stops17h 18m
Mon 10/512:21 pm -
2 stops12h 36m
Deal found 9/9![American Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/86:00 pm -
1 stop14h 15m
Mon 11/97:26 pm -
1 stop16h 24m
Deal found 9/6![Multiple Airlines logo]()
$385
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop15h 57m
Wed 10/2812:21 pm -
2 stops11h 03m
Deal found 9/11![American Airlines logo]()
$386
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/86:25 am -
2 stops13h 57m
Mon 11/94:55 pm -
1 stop8h 12m
Deal found 9/6![United Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/256:00 pm -
1 stop14h 57m
Mon 11/212:37 pm -
1 stop23h 13m
Deal found 9/6![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:38 am -
1 stop25h 54m
Mon 11/97:26 pm -
1 stop16h 24m
Deal found 9/6![Multiple Airlines logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:30 am -
1 stop22h 47m
Mon 11/212:37 pm -
1 stop23h 13m
Deal found 9/6![Multiple Airlines logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/226:00 pm -
1 stop14h 57m
Mon 11/212:37 pm -
1 stop23h 13m
Deal found 9/6![Multiple Airlines logo]()
$412
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 September 11, 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 September 11, 2026.
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2311:00 am -
2 stops10h 50m
Tue 3/26:15 am -
2 stops12h 22m
Deal found 9/8![Delta logo]()
$336
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:15 am -
2 stops12h 07m
Wed 11/42:35 pm -
2 stops10h 32m
Deal found 9/8![United Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:15 am -
2 stops12h 07m
Wed 11/118:25 am -
1 stop7h 35m
Deal found 9/8![United Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/269:26 am -
2 stops12h 24m
Sat 1/306:15 am -
2 stops9h 40m
Deal found 9/9![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/75:00 am -
1 stop8h 44m
Mon 10/121:00 am -
1 stop10h 29m
Deal found 9/6![United Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/86:25 am -
2 stops13h 57m
Mon 11/94:55 pm -
1 stop8h 12m
Deal found 9/6![United Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/299:26 am -
2 stops9h 34m
Sat 2/136:15 am -
2 stops12h 22m
Deal found 9/9![Delta logo]()
$436
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/108:15 am -
2 stops14h 21m
Fri 11/132:05 am -
2 stops15h 02m
Deal found 9/9![United Airlines logo]()
$441
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:15 am -
2 stops13h 42m
Tue 11/101:09 am -
2 stops10h 41m
Deal found 9/8![United Airlines logo]()
$451
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/248:10 am -
2 stops13h 47m
Sun 11/11:09 am -
2 stops12h 49m
Deal found 9/6![United Airlines logo]()
$522
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/218:17 am -
2 stops13h 52m
Sun 11/11:09 am -
1 stop24h 28m
Deal found 9/6![United Airlines logo]()
$615
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 -
2 stops33h 05m
Wed 10/71:19 pm -
2 stops10h 16m
Deal found 9/7![United Airlines logo]()
$1,735
Last-minute flights from Madison to Puerto RicoDiscover last-minute flight deals from Madison to Puerto Rico. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Puerto Rico. Data last updated September 11, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:10 am -
2 stops11h 28m
Sat 10/31:25 pm -
2 stops10h 10m
Deal found 9/9![United Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:06 pm -
2 stops17h 18m
Mon 10/512:21 pm -
2 stops12h 36m
Deal found 9/9![American Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/75:00 am -
1 stop8h 44m
Mon 10/121:00 am -
1 stop10h 29m
Deal found 9/6![United Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 10/127:30 am -
1 stop14h 46m
Deal found 9/10![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop15h 57m
Wed 10/2812:21 pm -
2 stops11h 03m
Deal found 9/11![American Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/226:00 pm -
1 stop14h 57m
Mon 11/212:37 pm -
1 stop23h 13m
Deal found 9/6![Multiple Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:05 pm -
1 stop17h 58m
Sat 10/316:00 am -
1 stop17h 32m
Deal found 9/10![American Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/248:10 am -
2 stops13h 47m
Sun 11/11:09 am -
2 stops12h 49m
Deal found 9/6![United Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/256:00 pm -
1 stop14h 57m
Mon 11/212:37 pm -
1 stop23h 13m
Deal found 9/6![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:30 am -
1 stop22h 47m
Mon 11/212:37 pm -
1 stop23h 13m
Deal found 9/6![Multiple Airlines logo]()
$411
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
1 stop8h 40m
Wed 11/47:40 am -
2 stops13h 27m
Deal found 9/8![United Airlines logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:38 am -
2 stops37h 21m
Sat 11/73:55 am -
1 stop15h 25m
Deal found 9/8![Multiple Airlines logo]()
$414
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 September 11, 2026.
Search for one-way flight options from Madison to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:27 am -
2 stops11h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$178
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 2/203:40 pm -
2 stops12h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![United Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:30 am -
1 stop27h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$190
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:00 am -
2 stops13h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:30 am -
1 stop22h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 pm -
3 stops45h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:00 pm -
1 stop15h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$216
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:15 am -
2 stops12h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$223
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:15 am -
2 stops13h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 pm -
1 stop15h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 pm -
1 stop14h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 pm -
1 stop14h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$238
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 September 11, 2026.
Round-trip from | $336 (Delta) |
|---|---|
One-way from | $178 (Delta) |
Popular in | April |
Cheapest in | October |
Average price | $418 |
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 7,457,451 searches. Data last updated September 11, 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
Wed 10/28
5:51 am-4:49 pm
1 stop9h 58m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$178
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Sat 2/20
3:40 pm-6:11 am
2 stops12h 31m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$183
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Sat 2/20
7:05 pm-3:07 pm
1 stop18h 02m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$183
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Sun 11/1
8:15 am-10:22 pm
2 stops12h 07m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$223
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Fri 11/27
6:29 pm-1:32 pm
1 stop17h 03m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$239
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Sat 1/9
3:40 pm-6:15 am
2 stops12h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$267
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Wed 9/16
5:50 am-4:49 pm
1 stop9h 59m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$310
MadisonAguadilla
MSN Madison Truax Field - BQN Aguadilla Borinquen
MSNBQN
Madison Truax Field
Sun 11/1
8:15 am-11:57 pm
2 stops13h 42m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$313
MadisonAguadilla
MSN Madison Truax Field - BQN Aguadilla Borinquen
MSNBQN
Madison Truax Field
Mon 11/2
8:15 am-11:57 pm
2 stops13h 42m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$313
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Tue 2/23
11:00 am-11:50 pm
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Tue 3/2
6:15 am-4:37 pm
2 stops12h 22m
$336
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
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
What is the cheapest month to book a flight from Madison to Puerto Rico?
Currently, October is the cheapest month in which you can book a flight from Madison to Puerto Rico (average of $315). Flying from Madison to Puerto Rico in April is currently the most expensive (average of $673). 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 35 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 September 11, 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.
Overall
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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.
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 September 11, 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 7,457,451 searches. Data last updated September 11, 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$580 | FlexibilityNo cancel fee | On-time71% |