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Madison

$133+ Cheap flights from San Juan 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from San Juan to Madison

Cheapest flights from San Juan to Madison
Explore the most affordable flight options available from San Juan to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

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 4/153:19 pm
SJU
-
MSN
1 stop9h 09m
American Airlines
Wed 4/2211:35 am
MSN
-
SJU
1 stop8h 16m
American Airlines
Deal found 2/10$266
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.
Tue 2/242:05 am
SJU
-
MSN
2 stops11h 48m
United Airlines
Sun 3/13:53 pm
MSN
-
SJU
2 stops12h 18m
United Airlines
Deal found 2/10$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.
Thu 7/212:59 am
SJU
-
MSN
1 stop9h 24m
American Airlines
Sun 7/127:00 am
MSN
-
SJU
1 stop16h 17m
American Airlines
Deal found 2/10$442
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 7/1612:59 am
SJU
-
MSN
1 stop9h 24m
American Airlines
Tue 7/287:02 am
MSN
-
SJU
1 stop14h 49m
American Airlines
Deal found 2/11$443
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:30 am
SJU
-
MSN
1 stop7h 51m
Frontier
Sun 3/295:46 pm
MSN
-
SJU
1 stop7h 27m
Frontier
Deal found 2/10$458
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.
Thu 7/162:35 pm
SJU
-
MSN
1 stop7h 05m
JetBlue
Tue 7/285:45 am
MSN
-
SJU
1 stop6h 48m
JetBlue
Deal found 2/10$476
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 2/237:00 am
SJU
-
MSN
2 stops10h 42m
American Airlines
Fri 2/278:24 pm
MSN
-
SJU
1 stop7h 00m
American Airlines
Deal found 2/10$510
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:30 am
SJU
-
MSN
1 stop8h 27m
United Airlines
Sat 2/285:44 pm
MSN
-
SJU
2 stops10h 27m
United Airlines
Deal found 2/9$520
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 7/143:40 pm
SJU
-
MSN
2 stops9h 03m
American Airlines
Sun 7/192:22 pm
MSN
-
SJU
1 stop7h 29m
American Airlines
Deal found 2/10$526

Find flight deals from San Juan to Madison

Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Madison (MSN). 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
(American Airlines)

One-way from

$133
(American Airlines)

Popular in

June

Cheapest in

August

Average price

$435
From San Juan to Madison Truax Field
Search Deals
One-way flight from San Juan to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($111 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from San Juan 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 February 13, 2026.
Use the filters below to find and compare flights from San Juan to Madison that are best for you.

Fly from

San Juan

Fly to

Madison

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/15

3:19 pm-11:28 pm

1 stop9h 09m

Madison Truax Field

Wed 4/22

11:35 am-8:51 pm

1 stop8h 16m

$266

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 4/17

3:56 pm-11:49 pm

1 stop8h 53m

Madison Truax Field

Tue 4/21

10:05 am-8:34 pm

1 stop9h 29m

$266

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 4/17

11:43 am-9:25 pm

2 stops10h 42m

Madison Truax Field

Tue 4/21

9:18 am-8:51 pm

2 stops10h 33m

$329

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 2/24

2:05 am-11:53 am

2 stops11h 48m

Madison Truax Field

Sun 3/1

3:53 pm-6:11 am

2 stops12h 18m

$430

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 2/25

10:20 am-4:52 pm

1 stop8h 32m

Madison Truax Field

Sun 3/1

11:22 am-11:31 pm

1 stop10h 09m

$430

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 7/16

12:59 am-9:23 am

1 stop9h 24m

Madison Truax Field

Tue 7/28

7:02 am-10:51 pm

1 stop14h 49m

$443

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 7/16

2:35 pm-8:40 pm

1 stop7h 05m

Madison Truax Field

Tue 7/28

5:45 am-1:33 pm

1 stop6h 48m

$476

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 2/24

2:05 am-2:07 pm

2 stops14h 02m

Madison Truax Field

Sat 2/28

2:48 pm-6:11 am

2 stops13h 23m

$520

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 4/16

11:43 am-9:25 pm

2 stops10h 42m

$133

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 4/17

3:56 pm-11:49 pm

1 stop8h 53m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 15 results
1
2

Best time to book a flight from San Juan to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from San Juan with our price prediction graph.
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 San Juan to Madison

What is the cheapest month to book a flight from San Juan to Madison?

Currently, September is the cheapest month in which you can book a flight from San Juan to Madison (average of $113). Flying from San Juan to Madison in June is currently the most expensive (average of $355). 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 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 February 13, 2026.
See what other customers who have flown with American Airlines from San Juan 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.
American Airlines
7.2
Good
11,275 reviews

Crew

8.0

Entertainment

6.9

Comfort

7.2

Overall

7.2

Boarding

7.5

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,275 reviews
American Airlines
7.2
Good
11,275 reviews

Crew

8.0

Entertainment

6.9

Comfort

7.2

Overall

7.2

Boarding

7.5

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from San Juan to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Madison from San Juan?

    If you book a flight to Madison from San Juan, you will be flying to Truax Field, which is the city’s only airport. Madison Truax Field (MSN) is located 5.4 mi from the center of Madison. There are 0 flights from San Juan to Truax Field per day from 1 airline.

  • How long is the flight from San Juan to Madison?

    Airlines like American Airlines and United Airlines fly from San Juan to Madison in about 8h 53m. The time it takes to get you to your destination can typically vary by up to 16m. The distance from San Juan to Madison is about 2180 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from San Juan to Madison round-trip?

    According to our current data, American Airlines ($265), offers the cheapest pricing from San Juan to Madison. You may be able to fly from San Juan to Madison for 39% less than the average price by searching for this airline.

  • Can I find deals for flights from San Juan to Madison that include hotel bookings?

    Yes. In addition to deals on San Juan to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Juan to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Juan to Madison.

  • Can I find deals for business class flights from San Juan to Madison?

    Yes. Cheapflights offers flight deals from San Juan to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Juan to Madison?

    Currently, September is the cheapest month in which you can book a flight from San Juan to Madison (average of $113). Flying from San Juan to Madison in June is currently the most expensive (average of $355). 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.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Top airline flying from San Juan to Madison

Discover the top airline that operate flights from San Juan 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 February 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$550FlexibilityNo cancel feeOn-time71%

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