$123+ Cheap flights from Puerto Rico to Madison (MSN)
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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Sep 17 — Sep 241
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico to Madison with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Puerto Rico to Madison
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Cheapest flights from Puerto Rico to MadisonExplore the most affordable flight options available from Puerto Rico to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2026.
Explore the most affordable flight options available from Puerto Rico to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2026.
This United Airlines deal was found by Cheapflights users on 8/16. 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 10/163:56 pm -
1 stop7h 39m
Sun 10/186:49 am -
1 stop6h 55m
Deal found 8/16![United Airlines logo]()
$316
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:39 pm -
1 stop18h 14m
Wed 11/1110:33 am -
2 stops12h 05m
Deal found 8/15![Multiple Airlines logo]()
$324
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.
Fri 10/233:56 pm -
1 stop7h 39m
Sun 11/16:25 am -
2 stops13h 57m
Deal found 8/15![United Airlines logo]()
$328
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:35 pm -
1 stop8h 22m
Sun 9/274:20 pm -
2 stops17h 40m
Deal found 8/15![American Airlines logo]()
$366
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:18 pm -
2 stops11h 07m
Wed 11/116:05 am -
2 stops10h 00m
Deal found 8/15![American Airlines logo]()
$380
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:39 pm -
1 stop18h 14m
Sun 9/276:00 pm -
1 stop22h 43m
Deal found 8/15![Multiple Airlines logo]()
$418
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:30 am -
1 stop10h 23m
Mon 11/237:05 am -
1 stop15h 08m
Deal found 8/15![American Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/211:00 am -
1 stop10h 14m
Sat 9/265:00 am -
2 stops14h 38m
Deal found 8/17![United Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 8/16. 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 10/1612:41 pm -
2 stops11h 31m
Sun 10/187:36 am -
2 stops13h 26m
Deal found 8/16![American Airlines logo]()
$496
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.
Mon 8/2412:55 am -
1 stop14h 10m
Sat 9/56:09 am -
1 stop15h 45m
Deal found 8/14![American Airlines logo]()
$508
Best flights from Puerto Rico to MadisonDiscover carefully curated flight deals from Puerto Rico to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 18, 2026.
Discover carefully curated flight deals from Puerto Rico to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 18, 2026.
This United Airlines deal was found by Cheapflights users on 8/16. 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 10/163:56 pm -
1 stop7h 39m
Sun 10/186:49 am -
1 stop6h 55m
Deal found 8/16![United Airlines logo]()
$316
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:39 pm -
1 stop18h 14m
Wed 11/1110:33 am -
2 stops12h 05m
Deal found 8/15![Multiple Airlines logo]()
$324
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:35 pm -
1 stop8h 22m
Sun 9/274:20 pm -
2 stops17h 40m
Deal found 8/15![American Airlines logo]()
$366
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.
Fri 10/233:56 pm -
1 stop7h 39m
Sun 11/16:25 am -
2 stops13h 57m
Deal found 8/15![United Airlines logo]()
$328
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/183:50 pm -
1 stop10h 23m
Mon 11/235:59 am -
2 stops13h 28m
Deal found 8/15![American Airlines logo]()
$426
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.
Tue 9/221:25 pm -
1 stop7h 48m
Sat 9/265:00 am -
1 stop8h 44m
Deal found 8/14![United Airlines logo]()
$431
Last-minute flights from Puerto Rico to MadisonDiscover last-minute flight deals from Puerto Rico to Madison. Data last updated August 18, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Madison. Data last updated August 18, 2026 and is based on user searches.
This Faresmojo 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:59 pm -
1 stop8h 39m
Sun 8/235:43 am -
1 stop6h 59m
Deal found 8/15![JetBlue logo]()
$602
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:37 pm -
1 stop17h 10m
Sun 8/237:55 pm -
2 stops33h 49m
Deal found 8/15![Multiple Airlines logo]()
$698
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.
Tue 8/187:00 am -
2 stops14h 53m
Sun 8/236:30 am -
2 stops13h 08m
Deal found 8/15![United Airlines logo]()
$968
This American Airlines deal was found by Cheapflights users on 8/17. 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 8/2312:55 am -
1 stop9h 22m
Mon 8/242:45 pm -
1 stop7h 30m
Deal found 8/17![American Airlines logo]()
$891
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.
Mon 8/2412:55 am -
1 stop14h 10m
Sat 9/56:09 am -
1 stop15h 45m
Deal found 8/14![American Airlines logo]()
$508
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.
Fri 8/283:47 pm -
2 stops9h 23m
Tue 9/16:30 am -
1 stop7h 21m
Deal found 8/13![American Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/211:00 am -
1 stop10h 14m
Sat 9/265:00 am -
2 stops14h 38m
Deal found 8/17![United Airlines logo]()
$431
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:35 pm -
1 stop8h 22m
Sun 9/274:20 pm -
2 stops17h 40m
Deal found 8/15![American Airlines logo]()
$366
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:39 pm -
1 stop18h 14m
Sun 9/276:00 pm -
1 stop22h 43m
Deal found 8/15![Multiple Airlines logo]()
$418
One-way flights from Puerto Rico to MadisonSearch for one-way flight options from Puerto Rico to Madison. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
Search for one-way flight options from Puerto Rico to Madison. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 am -
2 stops27h 53m
Deal found 8/17![Multiple Airlines logo]()
$123
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.
Tue 10/273:55 pm -
1 stop8h 12m
Deal found 8/14![United Airlines logo]()
$158
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.
Sat 12/56:28 am -
1 stop17h 18m
Deal found 8/13![American Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/106:55 pm -
3 stops39h 58m
Deal found 8/17![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/277:00 am -
1 stop11h 20m
Deal found 8/18![Multiple Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 8/17. 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 12/42:05 am -
2 stops14h 55m
Deal found 8/17![United Airlines logo]()
$228
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.
Mon 1/256:00 am -
1 stop14h 35m
Deal found 8/14![American Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 10/261:59 am -
3 stops32h 54m
Deal found 8/16![Multiple Airlines logo]()
$230
This American Airlines deal was found by Cheapflights users on 8/17. 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 12/197:00 am -
2 stops10h 56m
Deal found 8/17![American Airlines logo]()
$248
Find flight deals from Puerto Rico to Madison
Keep the following information in mind while searching for Puerto Rico to Madison flight deals. Data was last updated August 18, 2026.
Round-trip from | $316 (United Airlines) |
|---|---|
One-way from | $123 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $426 |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico to Madison 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 18, 2026.
Use the filters below to find and compare flights from Puerto Rico to Madison that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Fri 10/16
3:56 pm-10:35 pm
1 stop7h 39m
Madison Truax Field
Sun 10/18
6:49 am-2:44 pm
1 stop6h 55m
$316
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Fri 11/6
5:39 pm-9:53 am
1 stop18h 14m
Madison Truax Field
Wed 11/11
10:33 am-12:38 am
2 stops12h 05m
$324
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Fri 10/23
3:56 pm-10:35 pm
1 stop7h 39m
Madison Truax Field
Sun 11/1
6:25 am-10:22 pm
2 stops13h 57m
$328
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Fri 9/25
3:35 pm-10:57 pm
1 stop8h 22m
Madison Truax Field
Sun 9/27
4:20 pm-11:00 am
2 stops17h 40m
$366
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Wed 11/18
3:50 pm-12:13 am
1 stop10h 23m
Madison Truax Field
Mon 11/23
5:59 am-9:27 pm
2 stops13h 28m
$426
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Tue 9/22
1:25 pm-8:13 pm
1 stop7h 48m
Madison Truax Field
Sat 9/26
5:00 am-2:44 pm
1 stop8h 44m
$431
Cheapest one-way
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Mon 10/26
1:05 am-2:10 pm
2 stops14h 05m
$158
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Sat 12/5
6:28 am-9:46 pm
1 stop17h 18m
$183
Quickest one-way
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Sun 9/27
7:00 am-5:20 pm
1 stop11h 20m
$207
San JuanMadison
SJU San Juan Luis Munoz Marin Intl - MSN Madison Truax Field
SJUMSN
San Juan Luis Munoz Marin Intl
Fri 12/4
2:05 am-3:00 pm
2 stops14h 55m
$228
Sorted by cheapest first
Best time to book a flight from Puerto Rico to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Puerto Rico with our price prediction graph.
SJU-MSN
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 Puerto Rico to Madison
PR0-MSN
SJU-MSN
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Madison
Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated August 18, 2026.
See what other customers who have flown with American Airlines from Puerto Rico to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.4
Crew
7.9
Comfort
7.2
Entertainment
6.8
Overall
7.1
Boarding
7.5
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Food
6.4
Crew
7.9
Comfort
7.2
Entertainment
6.8
Overall
7.1
Boarding
7.5
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Madison?
Book flights to Madison if you plan to visit one of these locationsSun Prairie
Middleton
Fitchburg
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Complete your trip to Madison by adding a car rental and/or hotel reservation to your travel itinerary.
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Other flights to Madison
Explore flights to Madison departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 18, 2026.
Puerto Rico and Madison flights
Browse other Puerto Rico and Madison flight options. Last updated on August 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Puerto Rico to Madison
Discover the top airline that operate flights from Puerto Rico to Madison. 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 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$386 | Average$539 | FlexibilityNo cancel fee | On-time71% |