$110 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 3/6. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$319
American Airlines
Thu 6/4Mon 6/8
SJU - MSN • 1 stop
Cheapest one-way
$110
Typical prices: $207-$356
Frontier
Fri 3/6
SJU - MSN • 1 stop
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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, Jun 4 - Mon, Jun 8
American Airlines Logo
12:59 am - 9:23 am
SJU
-
MSN
9h 24m
1 stop
American Airlines Logo
7:02 am - 10:51 pm
MSN
-
SJU
14h 49m
1 stop
$319American Airlines
Wed, Mar 25 - Sun, Mar 29
Frontier Logo
3:08 am - 1:21 pm
SJU
-
MSN
11h 13m
1 stop
Frontier Logo
5:46 pm - 11:58 pm
MSN
-
SJU
29h 12m
1 stop
$323Frontier
Fri, Apr 17 - Fri, May 15
Multiple Airlines Logo
3:42 pm - 9:08 am
SJU
-
MSN
18h 26m
1 stop
Multiple Airlines Logo
6:50 pm - 2:08 pm
MSN
-
SJU
18h 18m
2 stops
$370Multiple Airlines
Wed, Mar 25 - Sun, Mar 29
Frontier Logo
3:08 am - 1:21 pm
SJU
-
MSN
11h 13m
1 stop
Frontier Logo
5:46 pm - 2:13 am
MSN
-
SJU
7h 27m
1 stop
$396Frontier
Wed, Mar 25 - Sun, Mar 29
American Airlines Logo
1:30 am - 10:39 am
SJU
-
MSN
10h 09m
1 stop
American Airlines Logo
8:24 pm - 4:24 am
MSN
-
SJU
7h 00m
1 stop
$411American Airlines
Fri, Apr 17 - Fri, May 15
American Airlines Logo
3:10 pm - 11:35 pm
SJU
-
MSN
9h 25m
1 stop
American Airlines Logo
8:24 pm - 2:19 pm
MSN
-
SJU
16h 55m
1 stop
$430American Airlines
Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
5:20 am - 5:56 pm
SJU
-
MSN
14h 36m
1 stop
Multiple Airlines Logo
6:36 pm - 10:17 am
MSN
-
SJU
13h 41m
1 stop
$465Multiple Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 2:07 pm
SJU
-
MSN
14h 02m
2 stops
United Airlines Logo
2:48 pm - 6:11 am
MSN
-
SJU
13h 23m
2 stops
$471United Airlines
Wed, Mar 25 - Sun, Mar 29
American Airlines Logo
1:30 am - 10:39 am
SJU
-
MSN
10h 09m
1 stop
American Airlines Logo
8:24 pm - 4:24 am
MSN
-
SJU
7h 00m
1 stop
$474American Airlines
Thu, Jul 16 - Tue, Jul 28
JetBlue Logo
2:40 pm - 10:35 pm
SJU
-
MSN
8h 55m
1 stop
JetBlue Logo
5:45 am - 1:33 pm
MSN
-
SJU
6h 48m
1 stop
$476JetBlue
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 are the most popular airlines flying to Truax Field?

The most popular airline among KAYAK users flying to Truax Field is American Airlines, followed by Delta and Southwest.

Good to know

Low seasonAugust
Cheapest flight$110
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 19% increase in price.
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.

  • 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.

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

    Each week there are around 442 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 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 11254 reviews
6.4Food
7.2Comfort
6.9Entertainment
7.5Boarding
8.0Crew
Airline reviews

Flight was on time and the meal and service were good.

10.0 ExcellentRyon, Feb 2026
DFW - TPA
Read more American Airlines reviews

Flight was on time and the meal and service were good.

Food was bad, sandwiche with cold cut meat was not labeled and and none of the flight attendants could tell what kind of meat it was (beef, pork or turkey). People have dietary and religious restrictions and "I dont know" is simply unacceptable. One flight attendant was extremely rude and unprofessional. Filed an formal complaint withAA regarding his behavior

Flight was delayed for 2 hours, then last minute the change to on time. The satélite location is far and a nightmare to get to.

This was a horrible experience. I’ve experienced several delays at this point and still not home. I was supposed to be home by 8:30 last night and here I sit at 7 am on a plane STILL unable to go home because of American Airlines.

Generally good. Flight left on time and the seats are comfortable. Plenty of space in front if you in you choose a comfort plus seat, completely worth spending the extra money given the amount of hours the flight lasts. The food tastes good but I would say it’s a the amount is too little. The crew was friendly and efficient. There was a some turbulence at different points into the flight. American Airlines has good deals to NZ if you book with plenty of time before you plan on going.

the plane was so hot!! the air-conditioning was barely blowing. The flight was delayed, and we had to sit on the hot plane before take off for an extended amount of time, waiting on international passengers. Would not have been so bad if it was not so hot. They said it would get better after take off, but it did not.

They are always late and seats was also not having working charger

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

did not have enough meal for first class passengers so offer us snack

Arrived 40 min early which was great - sat in runway for 35 min so no gain. Then waited for luggage 45 min. They need to staff accordingly knowing its one of the busiest week in Phx

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Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison