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$113+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
May 1 — May 81
Fri 5/1
Fri 5/8
1 adult, Economy
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Cheap 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 April 1, 2026.

This Faresmojo deal was found by Cheapflights users on 3/31. 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 5/77:30 am
SJU
-
MSN
1 stop9h 55m
JetBlue
Sun 5/105:43 am
MSN
-
SJU
1 stop6h 55m
JetBlue
Deal found 3/31$286
This Faresmojo deal was found by Cheapflights users on 3/31. 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.
Mon 6/12:48 pm
SJU
-
MSN
1 stop8h 56m
JetBlue
Tue 6/165:48 am
MSN
-
SJU
1 stop6h 43m
JetBlue
Deal found 3/31$321
This American Airlines deal was found by Cheapflights users on 3/30. 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 5/64:30 pm
SJU
-
MSN
1 stop8h 34m
American Airlines
Sat 5/1611:35 am
MSN
-
SJU
1 stop8h 20m
American Airlines
Deal found 3/30$334
This United Airlines deal was found by Cheapflights users on 3/30. 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 5/73:56 pm
SJU
-
MSN
1 stop7h 58m
United Airlines
Tue 5/128:10 am
MSN
-
SJU
2 stops12h 14m
United Airlines
Deal found 3/30$349
This Faresmojo deal was found by Cheapflights users on 3/31. 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.
Mon 6/17:30 am
SJU
-
MSN
1 stop9h 55m
JetBlue
Thu 6/115:48 am
MSN
-
SJU
1 stop6h 43m
JetBlue
Deal found 3/31$356
This Delta deal was found by Cheapflights users on 3/31. 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 5/12:45 pm
SJU
-
MSN
1 stop8h 42m
Delta
Wed 5/66:00 am
MSN
-
SJU
2 stops13h 26m
Delta
Deal found 3/31$358
This American Airlines deal was found by Cheapflights users on 3/31. 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 6/56:20 am
SJU
-
MSN
1 stop16h 00m
American Airlines
Mon 6/87:00 am
MSN
-
SJU
1 stop14h 45m
American Airlines
Deal found 3/31$399
This American Airlines deal was found by Cheapflights users on 3/30. 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 5/76:00 am
SJU
-
MSN
1 stop18h 28m
American Airlines
Sun 5/106:45 am
MSN
-
SJU
1 stop13h 06m
American Airlines
Deal found 3/30$409
This American Airlines deal was found by Cheapflights users on 4/1. 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 6/92:56 pm
SJU
-
MSN
2 stops10h 13m
American Airlines
Tue 6/305:00 am
MSN
-
SJU
2 stops12h 25m
American Airlines
Deal found 4/1$431
This United Airlines deal was found by Cheapflights users on 3/30. 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 5/17:20 am
SJU
-
MSN
2 stops15h 00m
United Airlines
Wed 5/66:30 am
MSN
-
SJU
2 stops13h 54m
United Airlines
Deal found 3/30$436

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 April 1, 2026.

Round-trip from

$286
(Faresmojo)

One-way from

$113
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$450
From Puerto Rico to Madison Truax Field
Search Deals
One-way flight from Puerto Rico to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 April 1, 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

Price

Cheapest round-trip

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 5/1

2:45 pm-10:27 pm

1 stop8h 42m

Madison Truax Field

Wed 5/6

6:00 am-8:26 pm

2 stops13h 26m

$358

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 5/7

6:00 am-11:28 pm

1 stop18h 28m

Madison Truax Field

Tue 5/12

7:10 am-11:03 pm

1 stop14h 53m

$399

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 6/5

6:20 am-5:22 pm

1 stop12h 02m

Madison Truax Field

Mon 6/8

7:00 am-10:45 pm

1 stop14h 45m

$399

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Mon 6/8

12:44 am-10:38 am

1 stop10h 54m

Madison Truax Field

Tue 6/30

5:00 am-6:25 pm

2 stops12h 25m

$431

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 5/1

7:20 am-9:20 pm

2 stops15h 00m

Madison Truax Field

Wed 5/6

6:30 am-9:24 pm

2 stops13h 54m

$436
Quickest round-trip

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 5/5

7:40 am-3:00 pm

1 stop8h 20m

Madison Truax Field

Sat 5/9

9:55 am-9:24 pm

2 stops10h 29m

$439
Cheapest one-way

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 5/1

7:30 am-4:17 pm

1 stop9h 47m

$113

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/15

6:15 am-4:17 pm

1 stop11h 02m

$153

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 4/23

3:56 pm-11:49 pm

1 stop8h 53m

$158
Quickest one-way

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/22

7:40 am-3:10 pm

1 stop8h 30m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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, September is the cheapest month in which you can book a flight from Puerto Rico to Madison (average of $113). Flying from Puerto Rico to Madison in June is currently the most expensive (average of $337). 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 April 1, 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.
American Airlines
7.1
Good
11,544 reviews

Overall

7.1

Food

6.4

Comfort

7.2

Crew

7.9

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,544 reviews
American Airlines
7.1
Good
11,544 reviews

Overall

7.1

Food

6.4

Comfort

7.2

Crew

7.9

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 8h 42m. Airlines will cover a distance of 2180 mi. This flight may include one or multiple stops.

  • 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, September is the cheapest month in which you can book a flight from Puerto Rico to Madison (average of $113). Flying from Puerto Rico to Madison in June is currently the most expensive (average of $337). 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
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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 April 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$550FlexibilityNo cancel feeOn-time71%

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