$118 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 2/6. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$235
Overall average: $582
American Airlines
Thu 1/22Tue 1/27
SJU - MSN • 1 stop
Cheapest one-way
$118
Typical prices: $194-$382
Delta
Fri 2/6
SJU - MSN • 2 stops
When to travel
September
Cheapest • 40% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Madison!
Flight Deals
Booking Insights
Flight Deals

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

Thu, Jan 22 - Tue, Jan 27
American Airlines Logo
6:00 am - 12:46 pm
SJU
-
MSN
8h 46m1 stop
American Airlines Logo
7:00 am - 8:50 pm
MSN
-
SJU
11h 50m2 stops
$235American Airlines
Wed, Apr 29 - Tue, May 5
American Airlines Logo
3:45 pm - 9:18 pm
SJU
-
MSN
6h 33m1 stop
American Airlines Logo
3:33 pm - 4:00 am
MSN
-
SJU
11h 27m1 stop
$298American Airlines
Tue, Apr 28 - Tue, May 5
United Airlines Logo
1:00 am - 11:44 am
SJU
-
MSN
11h 44m2 stops
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m1 stop
$325United Airlines
Thu, Jan 22 - Mon, Jan 26
United Airlines Logo
8:35 am - 2:10 pm
SJU
-
MSN
7h 35m1 stop
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m1 stop
$411United Airlines
Thu, Jan 22 - Mon, Jan 26
United Airlines Logo
8:35 am - 2:10 pm
SJU
-
MSN
7h 35m1 stop
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m1 stop
$432United Airlines
Wed, Jan 21 - Mon, Jan 26
United Airlines Logo
2:05 am - 2:10 pm
SJU
-
MSN
14h 05m2 stops
United Airlines Logo
12:32 pm - 12:36 am
MSN
-
SJU
10h 04m2 stops
$475United Airlines
Tue, Dec 30 - Sat, Jan 3
American Airlines Logo
8:25 am - 5:47 pm
SJU
-
MSN
11h 22m2 stops
American Airlines Logo
8:10 pm - 5:00 am
MSN
-
SJU
6h 50m1 stop
$499American Airlines
Sat, Mar 28 - Sat, Apr 4
American Airlines Logo
5:30 am - 7:54 pm
SJU
-
MSN
15h 24m1 stop
American Airlines Logo
8:24 pm - 4:21 am
MSN
-
SJU
6h 57m1 stop
$609American Airlines
Sat, Mar 28 - Sat, Apr 4
American Airlines Logo
5:30 am - 2:30 pm
SJU
-
MSN
10h 00m1 stop
American Airlines Logo
8:24 pm - 4:21 am
MSN
-
SJU
6h 57m1 stop
$610American Airlines
Mon, Dec 29 - Sat, Jan 3
United Airlines Logo
2:05 am - 11:48 am
SJU
-
MSN
11h 43m2 stops
United Airlines Logo
12:23 pm - 12:36 am
MSN
-
SJU
10h 13m2 stops
$781United Airlines
Booking Insights

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 September, where tickets cost $285 on average for one-way flights. On the other hand, the most expensive months are June and January, where the average cost of tickets from Puerto Rico is $592 and $582 respectively. For return trips, the best month to travel is September with an average price of $285.

Good to know

Low seasonFebruary
Cheapest flight$118
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 3% 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 tickets can be as cheap as $452. On the other hand, the most expensive day to fly is Saturday, where 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 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 516 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.

Reviews of the top airlines 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.
7.4
United AirlinesOverall score based on 9094 reviews
6.6Food
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
Airline reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

10.0 ExcellentRoger, Dec 2025
CAE - ORD
Read more United Airlines reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

Movie selection is good. Crew did not understand mileage program and were no help. Sick later. Food?

Staff on board was excellent. Positive upbeat helpful- like it used to be.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

For an expensive flight to another country, United has a lot of nerve serving pretzels and no meals (unless, of course, you want to buy something to eat). Unacceptable.

The food is terrible. The same pasta or chicken with bad taste and presentation

United have really come back. Airport and boarding process is clear and good, app and information also very good

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

It was probably one of the worst flights I’ve been on. The restrooms were never cleaned or stocked. The food was very subpar, and i usually enjoy airline food, so I was disappointed. It was just all around a bad experience. The only saving grace was the flight attendants.

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

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Everything you need to know for your flight to Madison

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