$119 Find Cheap Flights from Puerto Rico to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Madison departing on 9/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Madison

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Madison, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Madison, as well as popular online travel agencies
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Cheap Flights from Puerto Rico to Madison

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Puerto Rico to Madison that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Puerto Rico to Madison

Wed, Sep 24 - Sun, Sep 28
American Airlines Logo
4:42 pm - 9:59 amSJU-MSN
18h 17m2 stops
American Airlines Logo
7:10 am - 2:59 pmMSN-SJU
6h 49m1 stop
$310American Airlines
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Tue, Sep 23 - Sun, Sep 28
United Airlines Logo
1:05 am - 11:44 amSJU-MSN
11h 39m2 stops
United Airlines Logo
6:30 am - 2:44 pmMSN-SJU
7h 14m1 stop
$315United Airlines
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Thu, Nov 27 - Wed, Dec 3
United Airlines Logo
8:10 am - 2:54 pmSJU-MSN
8h 44m1 stop
United Airlines Logo
7:00 am - 10:22 pmMSN-SJU
13h 22m2 stops
$460United Airlines
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Tue, Sep 23 - Sun, Sep 28
United Airlines Logo
1:05 am - 11:44 amSJU-MSN
11h 39m2 stops
United Airlines Logo
2:46 pm - 12:34 pmMSN-SJU
20h 48m2 stops
$465United Airlines
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Fri, Jul 4 - Tue, Jul 8
American Airlines Logo
6:05 am - 4:21 pmSJU-MSN
11h 16m2 stops
American Airlines Logo
7:16 am - 12:27 amMSN-SJU
16h 11m1 stop
$470American Airlines
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Thu, Jul 3 - Tue, Jul 8
American Airlines Logo
12:59 am - 7:12 pmSJU-MSN
19h 13m1 stop
American Airlines Logo
6:27 am - 10:50 pmMSN-SJU
15h 23m1 stop
$510American Airlines
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Wed, Nov 26 - Wed, Dec 3
United Airlines Logo
2:05 am - 2:00 pmSJU-MSN
13h 55m2 stops
United Airlines Logo
7:00 am - 10:22 pmMSN-SJU
13h 22m2 stops
$537United Airlines
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Tue, Jul 8 - Sat, Jul 19
Logo
6:42 pm - 9:39 amSJU-MSN
15h 57m1 stop
Logo
10:19 am - 1:35 amMSN-SJU
14h 16m1 stop
$568
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Tue, Jul 8 - Sat, Jul 19
Logo
6:42 pm - 9:39 amSJU-MSN
15h 57m1 stop
Logo
6:25 pm - 9:09 pmMSN-SJU
25h 44m2 stops
$580
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Thu, Jul 3 - Sun, Jul 6
Delta Logo
2:35 pm - 11:28 pmSJU-MSN
9h 53m2 stops
Delta Logo
7:00 am - 4:28 pmMSN-SJU
8h 28m2 stops
$1,340Delta
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KAYAK's insights & trends for flights to Madison

Get data-powered insights and trends for flights to Madison to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly to Madison?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Madison, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Madison is August, where tickets cost $406 on average for return flights. On the other hand, the most expensive months are November and June, where the average cost of tickets from Puerto Rico is $708 and $694 respectively. For one-way flights, the best month to travel is August with an average price of $406.

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Good to know

Low seasonFebruary
High seasonDecember
Cheapest flight$119
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from San Juan to Madison

FAQs - booking Madison flights

  • How far is Madison Truax Field Airport from central Madison?

    Madison Truax Field Airport is 5 miles from the center of Madison.

  • What is the name of Madison’s airport?

    Madison is served by Madison Truax Field Airport, also commonly referred to as Truax Field. The airport code is MSN.

  • What is the cheapest day to fly to Madison?

    Based on KAYAK data, the cheapest day to fly to Madison is Tuesday where round-trip tickets can be as cheap as $452. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $617 on average.

  • How does KAYAK find such low prices on flights to Madison?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Madison.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Madison?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Madison?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Madison with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Madison?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Madison?

    The cheapest time of day to fly to Madison is generally in the morning, when round-trip flights cost $477 on average. The most expensive time of day to fly to Madison is generally in the evening, which is peak travel time and where the average cost of a ticket is $604.

  • How many direct flights to Madison are there each week?

    Each week there are around 386 direct flights from within Puerto Rico to Madison. The most common day for departures is Sunday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Madison

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Madison flight deals.

Top airline flying from Puerto Rico to Madison

 
See real verified KAYAK customer reviews for airlines flying to Madison. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Puerto Rico to Madison. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Madison? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 10000 reviews
6.5Food
7.5Boarding
7.2Comfort
6.9Entertainment
8.0Crew
Airline reviews

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

2.0 MediocreJose David, Jun 2025MIA - DTW
Read more American Airlines reviews

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

The pilots are always hauling in the sky. No issues with boarding only problem was layover was shortened too much by weather but luckily the next flight was still boarding and did not missit

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

Madison (MSN)

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