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$133+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Aug 1 — Aug 81
Sat 8/1
Sat 8/8
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 July 2, 2026.

This United Airlines deal was found by Cheapflights users on 6/29. 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
SJU
-
MSN
2 stops13h 42m
United Airlines
Mon 10/266:30 am
MSN
-
SJU
1 stop7h 10m
United Airlines
Deal found 6/29$266
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 am
SJU
-
MSN
1 stop10h 23m
Delta
Mon 9/286:00 am
MSN
-
SJU
1 stop9h 49m
Delta
Deal found 6/30$323
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 9/242:22 pm
SJU
-
MSN
1 stop10h 02m
American Airlines
Mon 9/288:05 pm
MSN
-
SJU
2 stops18h 35m
American Airlines
Deal found 7/1$326
This American Airlines deal was found by Cheapflights users on 6/28. 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 9/204:19 pm
SJU
-
MSN
1 stop19h 32m
American Airlines
Sun 10/256:00 am
MSN
-
SJU
1 stop15h 57m
American Airlines
Deal found 6/28$366
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Tue 8/412:55 am
SJU
-
MSN
1 stop9h 22m
American Airlines
Wed 8/1211:33 am
MSN
-
SJU
1 stop11h 26m
American Airlines
Deal found 6/30$371
This United Airlines deal was found by Cheapflights users on 6/28. 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 10/211:00 am
SJU
-
MSN
2 stops13h 37m
United Airlines
Sun 10/256:30 am
MSN
-
SJU
1 stop7h 10m
United Airlines
Deal found 6/28$408
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/1411:54 am
SJU
-
MSN
2 stops12h 48m
American Airlines
Wed 7/296:00 am
MSN
-
SJU
2 stops11h 24m
American Airlines
Deal found 7/1$428
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/1212:55 am
SJU
-
MSN
1 stop9h 22m
American Airlines
Mon 8/176:30 am
MSN
-
SJU
2 stops14h 25m
American Airlines
Deal found 6/30$446
This United Airlines deal was found by Cheapflights users on 7/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:00 am
SJU
-
MSN
2 stops13h 42m
United Airlines
Wed 9/26:30 am
MSN
-
SJU
1 stop7h 14m
United Airlines
Deal found 7/1$449

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 July 2, 2026.

Round-trip from

$266
(United Airlines)

One-way from

$133
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$413
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. 14% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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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 July 2, 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
Quickest round-trip

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Mon 9/21

1:00 am-1:42 pm

2 stops13h 42m

Madison Truax Field

Mon 10/26

6:30 am-2:40 pm

1 stop7h 10m

$266

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 9/24

2:22 pm-11:24 pm

1 stop10h 02m

Madison Truax Field

Mon 9/28

8:05 pm-3:40 pm

2 stops18h 35m

$326

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sun 9/20

6:27 am-3:39 pm

2 stops10h 12m

Madison Truax Field

Sun 10/25

6:00 am-10:57 pm

1 stop15h 57m

$389

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 7/14

11:54 am-11:42 pm

2 stops12h 48m

Madison Truax Field

Wed 7/29

6:00 am-6:24 pm

2 stops11h 24m

$428

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Mon 8/31

1:00 am-1:42 pm

2 stops13h 42m

Madison Truax Field

Wed 9/2

6:30 am-2:44 pm

1 stop7h 14m

$449
Cheapest one-way
Quickest one-way

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 10/27

7:25 am-1:50 pm

1 stop7h 25m

$133

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 9/3

7:00 am-4:20 pm

1 stop10h 20m

$163

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 7/24

7:25 am-11:42 pm

1 stop17h 17m

$163

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 8/14

6:00 am-9:47 am

2 stops28h 47m

$201

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 7/31

6:00 am-9:47 am

2 stops28h 47m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 12 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
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 July 2, 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
11,768 reviews

Crew

7.9

Food

6.4

Comfort

7.2

Entertainment

6.8

Overall

7.1

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.
American Airlines
7.1
Good
11,768 reviews
American Airlines
7.1
Good
11,768 reviews

Crew

7.9

Food

6.4

Comfort

7.2

Entertainment

6.8

Overall

7.1

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.

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 10h 02m. Airlines will cover a distance of 2180 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $118. Delta flights start at $123 while deals on American Airlines start at $181 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.

See more FAQs

Traveling to a place near Madison?

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

Browse thousands of different options on Cheapflights for your next trip

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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 July 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$481FlexibilityNo cancel feeOn-time71%

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