$133+ Cheap flights from Madison (MSN) to San Juan
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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Mar 15 — Mar 221
1 adult, Economy
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Find cheap flights from Madison to San Juan 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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Cheapest flights from Madison to San JuanExplore the most affordable flight options available from Madison to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.
Explore the most affordable flight options available from Madison to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.
This United Airlines deal was found by Cheapflights users on 2/10. 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 5/36:30 am
MSN
- SJU
1 stop7h 14m
United Airlines
Fri 5/81:00 am
SJU
- MSN
2 stops13h 44m
United Airlines
Deal found 2/10![United Airlines logo]()
$266
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/141:05 pm
MSN
- SJU
1 stop8h 00m
American Airlines
Tue 4/213:10 pm
SJU
- MSN
1 stop18h 38m
American Airlines
Deal found 2/10![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Sat 5/166:20 am
MSN
- SJU
1 stop14h 45m
American Airlines
Wed 5/2712:59 am
SJU
- MSN
1 stop7h 46m
American Airlines
Deal found 2/9![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/98:24 pm
MSN
- SJU
1 stop7h 00m
American Airlines
Wed 3/187:40 am
SJU
- MSN
1 stop16h 55m
American Airlines
Deal found 2/10![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Tue 10/206:15 am
MSN
- SJU
2 stops10h 50m
American Airlines
Tue 10/278:30 am
SJU
- MSN
2 stops13h 40m
American Airlines
Deal found 2/11![American Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:50 pm
MSN
- SJU
2 stops26h 58m
Multiple Airlines
Fri 5/153:42 pm
SJU
- MSN
1 stop18h 32m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:00 am
MSN
- SJU
2 stops12h 12m
Delta
Wed 3/44:30 pm
SJU
- MSN
1 stop8h 18m
Delta
Deal found 2/10![Delta logo]()
$348
This American Airlines deal was found by Cheapflights users on 2/11. 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 4/86:01 am
MSN
- SJU
2 stops11h 09m
American Airlines
Mon 4/1311:59 pm
SJU
- MSN
1 stop12h 06m
American Airlines
Deal found 2/11![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/243:27 pm
MSN
- SJU
1 stop13h 01m
American Airlines
Tue 4/146:00 am
SJU
- MSN
1 stop7h 35m
American Airlines
Deal found 2/10![American Airlines logo]()
$378
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/256:20 am
MSN
- SJU
2 stops9h 52m
American Airlines
Sun 5/106:00 am
SJU
- MSN
1 stop18h 28m
American Airlines
Deal found 2/10![American Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/98:00 am
MSN
- SJU
2 stops11h 34m
American Airlines
Tue 3/176:00 am
SJU
- MSN
2 stops10h 50m
American Airlines
Deal found 2/10![American Airlines logo]()
$401
This Faresmojo deal was found by Cheapflights users on 2/13. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:38 am
MSN
- SJU
1 stop9h 49m
JetBlue
Thu 2/263:55 pm
SJU
- MSN
1 stop8h 29m
JetBlue
Deal found 2/13![JetBlue logo]()
$406
Best flights from Madison to San JuanDiscover carefully curated flight deals from Madison to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 13, 2026.
Discover carefully curated flight deals from Madison to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 13, 2026.
This Delta deal was found by Cheapflights users on 2/10. 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.
Sun 5/36:00 am
MSN
- SJU
2 stops13h 24m
Delta
Sat 5/97:00 am
SJU
- MSN
2 stops11h 32m
Delta
Deal found 2/10![Delta logo]()
$266
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Mon 4/136:20 am
MSN
- SJU
2 stops10h 50m
American Airlines
Fri 4/1711:43 am
SJU
- MSN
2 stops10h 42m
American Airlines
Deal found 2/12![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Sat 2/282:48 pm
MSN
- SJU
2 stops13h 23m
United Airlines
Wed 3/48:30 am
SJU
- MSN
1 stop8h 27m
United Airlines
Deal found 2/10![United Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/38:09 am
MSN
- SJU
2 stops11h 25m
American Airlines
Wed 3/117:40 am
SJU
- MSN
1 stop16h 55m
American Airlines
Deal found 2/10![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 2/11. 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.
Tue 2/247:00 am
MSN
- SJU
2 stops12h 12m
Delta
Wed 3/44:30 pm
SJU
- MSN
1 stop8h 18m
Delta
Deal found 2/11![Delta logo]()
$348
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/115:08 pm
MSN
- SJU
1 stop16h 40m
American Airlines
Tue 4/1411:43 am
SJU
- MSN
2 stops11h 25m
American Airlines
Deal found 2/10![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Tue 4/146:20 am
MSN
- SJU
1 stop7h 09m
American Airlines
Tue 4/217:25 am
SJU
- MSN
1 stop16h 36m
American Airlines
Deal found 2/12![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Tue 2/247:15 am
MSN
- SJU
2 stops12h 19m
American Airlines
Wed 3/47:00 am
SJU
- MSN
2 stops11h 07m
American Airlines
Deal found 2/11![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Wed 4/228:00 am
MSN
- SJU
2 stops11h 51m
American Airlines
Mon 4/273:10 pm
SJU
- MSN
1 stop18h 35m
American Airlines
Deal found 2/10![American Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 5/169:18 am
MSN
- SJU
2 stops10h 37m
American Airlines
Sat 5/236:01 am
SJU
- MSN
1 stop12h 21m
American Airlines
Deal found 2/12![American Airlines logo]()
$392
Last-minute flights from Madison to San JuanDiscover last-minute flight deals from Madison to San Juan. Data last updated February 13, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to San Juan. Data last updated February 13, 2026 and is based on user searches.
This Faresmojo deal was found by Cheapflights users on 2/13. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:38 am
MSN
- SJU
1 stop9h 49m
JetBlue
Thu 2/263:55 pm
SJU
- MSN
1 stop8h 29m
JetBlue
Deal found 2/13![JetBlue logo]()
$406
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:00 am
MSN
- SJU
2 stops12h 12m
Delta
Wed 3/44:30 pm
SJU
- MSN
1 stop8h 18m
Delta
Deal found 2/10![Delta logo]()
$348
This American Airlines deal was found by Cheapflights users on 2/10. 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 2/278:24 pm
MSN
- SJU
1 stop7h 00m
American Airlines
Wed 3/43:51 pm
SJU
- MSN
1 stop7h 13m
American Airlines
Deal found 2/10![American Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 2/12. 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 2/283:53 pm
MSN
- SJU
2 stops12h 18m
United Airlines
Tue 3/32:05 am
SJU
- MSN
2 stops11h 48m
United Airlines
Deal found 2/12![United Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/38:09 am
MSN
- SJU
2 stops11h 25m
American Airlines
Wed 3/117:40 am
SJU
- MSN
1 stop16h 55m
American Airlines
Deal found 2/10![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 2/11. 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 3/38:15 am
MSN
- SJU
2 stops12h 07m
United Airlines
Wed 3/117:30 am
SJU
- MSN
1 stop8h 28m
United Airlines
Deal found 2/11![United Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/98:24 pm
MSN
- SJU
1 stop7h 00m
American Airlines
Wed 3/187:40 am
SJU
- MSN
1 stop16h 55m
American Airlines
Deal found 2/10![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/98:00 am
MSN
- SJU
2 stops11h 34m
American Airlines
Tue 3/176:00 am
SJU
- MSN
2 stops10h 50m
American Airlines
Deal found 2/10![American Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/243:27 pm
MSN
- SJU
1 stop13h 01m
American Airlines
Tue 4/146:00 am
SJU
- MSN
1 stop7h 35m
American Airlines
Deal found 2/10![American Airlines logo]()
$378
This Faresmojo deal was found by Cheapflights users on 2/10. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:30 am
MSN
- SJU
1 stop6h 57m
JetBlue
Tue 4/73:30 pm
SJU
- MSN
1 stop8h 28m
JetBlue
Deal found 2/10![JetBlue logo]()
$416
One-way flights from Madison to San JuanSearch for one-way flight options from Madison to San Juan. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
Search for one-way flight options from Madison to San Juan. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
This Delta deal was found by Cheapflights users on 2/10. 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 4/86:00 am
MSN
- SJU
1 stop7h 15m
Delta
Deal found 2/10![Delta logo]()
$133
This American Airlines deal was found by Cheapflights users on 2/10. 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 5/196:20 am
MSN
- SJU
1 stop14h 45m
American Airlines
Deal found 2/10![American Airlines logo]()
$137
This United Airlines deal was found by Cheapflights users on 2/11. 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.
Sun 4/198:30 am
MSN
- SJU
2 stops11h 54m
United Airlines
Deal found 2/11![United Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Wed 4/86:00 am
MSN
- SJU
2 stops11h 10m
American Airlines
Deal found 2/10![American Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 2/10. 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.
Sun 4/56:00 am
MSN
- SJU
1 stop7h 15m
Delta
Deal found 2/10![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/10. 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 3/13:53 pm
MSN
- SJU
2 stops12h 18m
United Airlines
Deal found 2/10![United Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 2/10. 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 2/238:24 pm
MSN
- SJU
1 stop7h 00m
American Airlines
Deal found 2/10![American Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 4/89:48 am
MSN
- SJU
3 stops37h 41m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 2/11. 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 4/97:45 am
MSN
- SJU
2 stops12h 06m
American Airlines
Deal found 2/11![American Airlines logo]()
$236
Find flight deals from Madison to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 13, 2026.
Round-trip from | $266 (Delta) |
|---|---|
One-way from | $133 (Delta) |
Popular in | March |
Cheapest in | September |
Average price | $517 |
Cheapflights Fare Finder
Customize your flight search to find flights from Madison to San Juan 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 February 13, 2026.
Use the filters below to find and compare flights from Madison to San Juan that are best for you.
Fly from
Madison
Fly to
San Juan
Route
Depart
Return
Price
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sun 5/3
6:00 am-8:24 pm
2 stops13h 24m
San Juan Luis Munoz Marin Intl
Sat 5/9
7:00 am-5:32 pm
2 stops11h 32m
$266
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Mon 4/13
6:20 am-6:10 pm
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Fri 4/17
11:43 am-9:25 pm
2 stops10h 42m
$329
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Tue 3/3
8:09 am-9:34 pm
2 stops11h 25m
San Juan Luis Munoz Marin Intl
Wed 3/11
7:40 am-11:35 pm
1 stop16h 55m
$329
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sat 4/11
5:08 pm-10:48 am
1 stop16h 40m
San Juan Luis Munoz Marin Intl
Tue 4/14
11:43 am-10:08 pm
2 stops11h 25m
$329
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Tue 4/14
6:20 am-2:29 pm
1 stop7h 09m
San Juan Luis Munoz Marin Intl
Tue 4/21
7:25 am-11:01 pm
1 stop16h 36m
$329
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sat 2/28
2:48 pm-6:11 am
2 stops13h 23m
San Juan Luis Munoz Marin Intl
Wed 3/4
8:30 am-2:57 pm
1 stop8h 27m
$348
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Tue 2/24
7:00 am-9:12 pm
2 stops12h 12m
San Juan Luis Munoz Marin Intl
Wed 3/4
4:30 pm-10:48 pm
1 stop8h 18m
$348
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Tue 2/24
7:15 am-9:34 pm
2 stops12h 19m
San Juan Luis Munoz Marin Intl
Wed 3/4
7:00 am-4:07 pm
2 stops11h 07m
$348
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Wed 4/22
8:00 am-8:51 pm
2 stops11h 51m
San Juan Luis Munoz Marin Intl
Mon 4/27
3:10 pm-8:45 am
1 stop18h 35m
$392
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Sat 5/16
9:18 am-8:55 pm
2 stops10h 37m
San Juan Luis Munoz Marin Intl
Sat 5/23
6:01 am-5:22 pm
1 stop12h 21m
$392
Showing 1-10 of 20 results
Best time to book a flight from Madison to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from Madison with our price prediction graph.
MSN-PR1
MSN-SJU
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 San Juan
MSN-PR1
MSN-SJU
How far ahead should I book a flight from Madison to San Juan?
Use this chart to determine the optimal time to book a round-trip flight from Madison to San Juan. Price data was last updated on February 6, 2026.
The best time to book flights from Madison to San Juan is 21 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Madison to San Juan?
Currently, November is the cheapest month in which you can book a flight from Madison to San Juan (average of $113). Flying from Madison to San Juan in June is currently the most expensive (average of $375). 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.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated February 13, 2026.
Read through reviews of airlines operating flights from Madison to San Juan, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Food
7.2
Comfort
7.9
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Food
7.2
Comfort
7.9
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Food
7.2
Comfort
7.9
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Food
7.2
Comfort
7.9
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Madison to San Juan. 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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Madison and San Juan flights
Browse other Madison and San Juan flight options. Last updated on February 13, 2026.
Other flights from Madison
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Top 3 airlines flying from Madison to San Juan
Discover the top 3 airlines that operate flights from Madison to San Juan. 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 February 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$225 | Average$477 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$257 | Average$512 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$268 | Average$522 | FlexibilityNo cancel fee | On-time71% |