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Madison

$190+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
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Cheap 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 21, 2025.

Round-trip from

$215
(American Airlines)

One-way from

$190
(Delta)

Popular in

October

Cheapest in

September

Average price

$370
From Puerto Rico to Madison Truax Field
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One-way flight from Puerto Rico to Madison Truax Field
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Highest demand for flights based on searches. 25% potential increase in price ($205 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($65 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Puerto Rico to Madison

Cheapest flights from Puerto Rico to Madison
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 21, 2025.

This American Airlines deal was found by Cheapflights users on 8/21. 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.
Fri 9/124:43 pmSJU - MSN
2 stops17h 22mAmerican Airlines
Wed 9/243:51 pmMSN - SJU
2 stops18h 20mAmerican Airlines
Deal found 8/21$215
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Fri 9/264:43 pmSJU - MSN
1 stop7h 27mAmerican Airlines
Sun 9/287:10 amMSN - SJU
1 stop6h 49mAmerican Airlines
Deal found 8/20$337
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Mon 12/227:20 amSJU - MSN
1 stop12h 18mAmerican Airlines
Tue 1/1311:43 amMSN - SJU
1 stop9h 57mAmerican Airlines
Deal found 8/21$420
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/283:50 pmSJU - MSN
1 stop9h 09mAmerican Airlines
Mon 9/17:16 amMSN - SJU
1 stop14h 40mAmerican Airlines
Deal found 8/18$479
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Fri 8/223:56 pmSJU - MSN
1 stop7h 30mUnited Airlines
Sun 8/246:30 amMSN - SJU
1 stop7h 14mUnited Airlines
Deal found 8/20$509
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Thu 9/111:05 amSJU - MSN
2 stops9h 40mUnited Airlines
Wed 9/2410:50 amMSN - SJU
2 stops12h 07mUnited Airlines
Deal found 8/21$567
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Fri 8/227:55 amSJU - MSN
2 stops14h 57mAmerican Airlines
Sun 8/248:14 pmMSN - SJU
1 stop16h 51mAmerican Airlines
Deal found 8/20$582

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 21, 2025.
Use the filters below to find and compare flights from Puerto Rico to Madison that are best for you.

Fly from

Puerto Rico

Fly to

Madison

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 9/12

4:43 pm-9:05 am

2 stops17h 22m

Madison Truax Field

Wed 9/24

3:51 pm-11:11 am

2 stops18h 20m

$215

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 9/26

4:43 pm-11:10 pm

1 stop7h 27m

Madison Truax Field

Sun 9/28

7:10 am-2:59 pm

1 stop6h 49m

$337

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 8/28

3:50 pm-11:59 pm

1 stop9h 09m

Madison Truax Field

Mon 9/1

7:16 am-10:56 pm

1 stop14h 40m

$479

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 9/11

1:05 am-9:45 am

2 stops9h 40m

Madison Truax Field

Wed 9/24

10:50 am-11:57 pm

2 stops12h 07m

$567

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 9/25

1:05 am-1:50 pm

2 stops13h 45m

Madison Truax Field

Sun 9/28

6:30 am-2:44 pm

1 stop7h 14m

$632

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 9/5

2:20 pm-10:14 pm

1 stop8h 54m

$190

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 9/5

6:10 am-9:10 pm

2 stops16h 00m

$230

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 8/27

6:00 am-4:45 pm

2 stops11h 45m

$290

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 9/4

1:05 am-11:44 am

2 stops11h 39m

$324

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 10/15

5:30 am-12:15 pm

1 stop7h 45m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 12 results
1
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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.
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

What is the cheapest month to book a flight from Puerto Rico to Madison?

Currently, January is the cheapest month in which you can book a flight from Puerto Rico to Madison (average of $338). Flying from Puerto Rico to Madison in March is currently the most expensive (average of $422). 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.

What is the cheapest time of day to fly from PR to MSN?

Find hourly flight availability from Puerto Rico to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2025.

When flying from Puerto Rico to Madison, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 21, 2025.
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.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Food

6.5

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Food

6.5

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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.

  • What airport do you fly into for flights to Madison from Puerto Rico?

    Madison Truax Field (MSN) is the airport you will fly into if you book a flight from Puerto Rico to Madison. It is only a 5.4 mi journey from Truax Field (MSN) to Madison’s city center.

  • How long is the flight from Puerto Rico to Madison?

    Departing from Puerto Rico to Madison will take you 17h 22m. Airlines will cover a distance of 2180 mi.

  • What are the cheapest airlines to fly from Puerto Rico to Madison one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $190. American Airlines flights start at $230 while deals on United Airlines start at $324 one-way.

  • Can I find deals for flights from Puerto Rico to Madison that include hotel bookings?

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

  • How can I find direct flights from Puerto Rico to Madison?

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

  • Can I find deals for business class flights from Puerto Rico to Madison?

    Yes. Cheapflights offers flight deals from Puerto Rico 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 Puerto Rico to Madison?

    Currently, January is the cheapest month in which you can book a flight from Puerto Rico to Madison (average of $338). Flying from Puerto Rico to Madison in March is currently the most expensive (average of $422). 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?

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Baraboo
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Alternative routes for Puerto Rico to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$510FlexibilityNo cancel feeOn-time71%

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