$153+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Nov 24 — Dec 11
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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One-way
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 October 25, 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 October 25, 2026.
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/148:15 am -
2 stops12h 07m
Wed 11/182:52 pm -
2 stops10h 15m
Deal found 10/24![United Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/109:15 am -
2 stops9h 58m
Sat 11/1411:35 am -
1 stop14h 24m
Deal found 10/20![American Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/1210:38 am -
1 stop7h 11m
Fri 12/186:00 am -
2 stops29h 58m
Deal found 10/23![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/1210:38 am -
2 stops12h 41m
Wed 12/164:04 pm -
1 stop27h 26m
Deal found 10/23![Multiple Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/319:53 am -
2 stops14h 51m
Fri 1/155:15 pm -
1 stop7h 40m
Deal found 10/22![Delta logo]()
$471
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/128:10 am -
1 stop11h 02m
Sat 12/196:26 pm -
1 stop7h 26m
Deal found 10/23![American Airlines logo]()
$476
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/256:55 am -
2 stops12h 41m
Sun 12/66:38 pm -
1 stop7h 11m
Deal found 10/24![American Airlines logo]()
$481
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/136:30 am -
2 stops13h 52m
Thu 12/172:52 pm -
1 stop10h 48m
Deal found 10/23![United Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/118:15 am -
2 stops12h 07m
Tue 12/222:52 pm -
1 stop10h 48m
Deal found 10/23![United Airlines logo]()
$511
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/136:25 am -
1 stop7h 15m
Wed 11/182:52 pm -
1 stop10h 45m
Deal found 10/24![United Airlines logo]()
$516
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 52m
Deal found 10/20![United Airlines logo]()
$606
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/266:06 am -
1 stop15h 51m
Thu 12/311:09 am -
2 stops17h 37m
Deal found 10/20![United Airlines logo]()
$1,224
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 October 25, 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 October 25, 2026.
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/316:15 am -
1 stop7h 55m
Tue 2/95:15 pm -
1 stop7h 40m
Deal found 10/23![Delta logo]()
$416
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/148:15 am -
2 stops12h 07m
Wed 11/182:52 pm -
2 stops10h 15m
Deal found 10/24![United Airlines logo]()
$421
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/136:25 am -
1 stop7h 15m
Wed 11/182:52 pm -
1 stop10h 45m
Deal found 10/24![United Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 3/237:00 am -
2 stops12h 20m
Tue 3/306:15 am -
2 stops15h 30m
Deal found 10/22![Delta logo]()
$526
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/16:40 am -
2 stops12h 33m
Fri 1/155:15 pm -
1 stop7h 40m
Deal found 10/22![Delta logo]()
$574
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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
Tue 11/102:05 am -
2 stops11h 50m
Deal found 10/21![United Airlines logo]()
$606
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/16:40 am -
2 stops12h 33m
Wed 1/137:30 am -
2 stops15h 15m
Deal found 10/22![Delta logo]()
$574
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 52m
Deal found 10/21![United Airlines logo]()
$606
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/263:47 pm -
2 stops30h 10m
Thu 12/311:09 am -
2 stops17h 37m
Deal found 10/20![United Airlines logo]()
$1,254
Last-minute flights from Madison to Puerto RicoDiscover last-minute flight deals from Madison to Puerto Rico. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Puerto Rico. Data last updated October 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 -
2 stops10h 16m
Wed 11/117:25 pm -
1 stop23h 55m
Deal found 10/23![Multiple Airlines logo]()
$537
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/75:00 am -
2 stops14h 13m
Sat 11/147:30 am -
2 stops11h 37m
Deal found 10/22![American Airlines logo]()
$541
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 52m
Deal found 10/20![United Airlines logo]()
$606
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/109:15 am -
2 stops9h 58m
Sat 11/1411:35 am -
1 stop14h 24m
Deal found 10/20![American Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/106:25 am -
2 stops12h 59m
Fri 11/132:05 am -
2 stops15h 06m
Deal found 10/20![United Airlines logo]()
$511
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/136:25 am -
1 stop7h 15m
Wed 11/182:52 pm -
1 stop10h 45m
Deal found 10/24![United Airlines logo]()
$516
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/148:15 am -
2 stops12h 07m
Wed 11/182:52 pm -
2 stops10h 15m
Deal found 10/24![United Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/2110:38 am -
2 stops34h 53m
Mon 11/303:43 am -
1 stop8h 07m
Deal found 10/23![Multiple Airlines logo]()
$564
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/226:00 pm -
2 stops19h 00m
Mon 11/303:43 am -
1 stop8h 07m
Deal found 10/23![Multiple Airlines logo]()
$563
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/2311:22 am -
1 stop10h 51m
Tue 12/14:42 pm -
1 stop9h 17m
Deal found 10/24![American Airlines logo]()
$526
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/256:55 am -
2 stops12h 41m
Sun 12/66:38 pm -
1 stop7h 11m
Deal found 10/24![American Airlines logo]()
$481
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 October 25, 2026.
Search for one-way flight options from Madison to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/156:00 pm -
1 stop15h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/156:00 pm -
2 stops28h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$176
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 1/126:05 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$198
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/155:30 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/246:00 pm -
2 stops20h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$212
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/156:02 am -
2 stops10h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/176:00 pm -
1 stop31h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$216
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/117:05 am -
1 stop15h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/246:00 pm -
1 stop31h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/176:00 pm -
3 stops54h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$221
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/275:59 am -
2 stops13h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/1211:05 am -
3 stops37h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$234
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 October 25, 2026.
Round-trip from | $396 (Delta) |
|---|---|
One-way from | $153 (Kiwi.com) |
Popular in | April |
Cheapest in | August |
Average price | $489 |
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 October 25, 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 11/15
5:30 am-3:05 pm
1 stop7h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$198
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Tue 1/12
6:05 am-3:40 pm
1 stop7h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$198
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Mon 11/30
6:29 pm-10:41 am
2 stops14h 12m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$213
MadisonAguadilla
MSN Madison Truax Field - BQN Aguadilla Borinquen
MSNBQN
Madison Truax Field
Sun 1/17
10:45 am-11:57 pm
2 stops11h 12m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$248
MadisonAguadilla
MSN Madison Truax Field - BQN Aguadilla Borinquen
MSNBQN
Madison Truax Field
Sun 1/24
8:15 am-11:57 pm
2 stops13h 42m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$248
MadisonSan Juan
MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl
MSNSJU
Madison Truax Field
Sat 1/16
8:15 am-12:36 am
2 stops14h 21m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$263
MadisonAguadilla
MSN Madison Truax Field - BQN Aguadilla Borinquen
MSNBQN
Madison Truax Field
Fri 2/26
8:19 am-11:57 pm
2 stops13h 38m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$293
MadisonAguadilla
MSN Madison Truax Field - BQN Aguadilla Borinquen
MSNBQN
Madison Truax Field
Mon 11/30
2:40 pm-2:45 am
3 stops34h 05m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$346
MadisonAguadilla
MSN Madison Truax Field - BQN Aguadilla Borinquen
MSNBQN
Madison Truax Field
Sun 11/15
8:15 am-11:57 pm
2 stops13h 42m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$388
MadisonAguadilla
MSN Madison Truax Field - BQN Aguadilla Borinquen
MSNBQN
Madison Truax Field
Sun 1/17
6:40 pm-2:00 pm
3 stops41h 20m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$389
Showing 1-10 of 19 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
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
What is the cheapest month to book a flight from Madison to Puerto Rico?
Currently, August is the cheapest month in which you can book a flight from Madison to Puerto Rico (average of $366). Flying from Madison to Puerto Rico in April is currently the most expensive (average of $667). 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 90 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 October 25, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican Airlines from Madison to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Overall
7.8
Comfort
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Related info for your journey
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Madison and Puerto Rico flights
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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 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$235 | Average$522 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$601 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$309 | Average$584 | FlexibilityNo cancel fee | On-time71% |