$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
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
$277
Overall average: $520
American Airlines
Thu 4/30Tue 5/5
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 • 42% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, Apr 30 - Tue, May 5
American Airlines Logo
11:59 pm - 11:04 am
SJU
-
MSN
12h 05m1 stop
American Airlines Logo
6:10 am - 10:05 pm
MSN
-
SJU
14h 55m1 stop
$277American Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m1 stop
United Airlines Logo
2:48 pm - 6:11 am
MSN
-
SJU
13h 23m2 stops
$326United Airlines
Thu, Apr 30 - Wed, May 6
American Airlines Logo
11:59 pm - 11:04 am
SJU
-
MSN
12h 05m1 stop
American Airlines Logo
7:55 am - 6:06 pm
MSN
-
SJU
9h 11m2 stops
$341American Airlines
Wed, Apr 29 - Wed, May 6
United Airlines Logo
1:00 am - 11:38 am
SJU
-
MSN
11h 38m2 stops
United Airlines Logo
6:30 am - 8:38 pm
MSN
-
SJU
13h 08m2 stops
$369United Airlines
Thu, Apr 30 - Wed, May 6
American Airlines Logo
11:59 pm - 11:04 am
SJU
-
MSN
12h 05m1 stop
American Airlines Logo
11:35 am - 8:51 pm
MSN
-
SJU
8h 16m1 stop
$395American Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m1 stop
United Airlines Logo
3:53 pm - 9:00 pm
MSN
-
SJU
27h 07m1 stop
$476United Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m1 stop
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m1 stop
$581United Airlines
Fri, Mar 27 - Sat, Apr 4
American Airlines Logo
1:30 am - 10:36 am
SJU
-
MSN
10h 06m1 stop
American Airlines Logo
6:44 am - 5:11 pm
MSN
-
SJU
9h 27m1 stop
$694American Airlines
Fri, Mar 27 - Sat, Apr 4
American Airlines Logo
1:30 am - 10:36 am
SJU
-
MSN
10h 06m1 stop
American Airlines Logo
6:44 am - 2:49 pm
MSN
-
SJU
7h 05m1 stop
$695American Airlines
Sat, Mar 28 - Sat, Apr 4
American Airlines Logo
7:40 am - 5:15 pm
SJU
-
MSN
10h 35m2 stops
American Airlines Logo
6:44 am - 5:11 pm
MSN
-
SJU
9h 27m1 stop
$798American 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 January and June, where the average cost of tickets from Puerto Rico is $864 and $592 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 6% increase in price.
Most popular time to fly with an average 5% 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 324 direct flights from within Puerto Rico to Madison. The most common day for departures is Friday, 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 11083 reviews
7.5Boarding
6.4Food
8.0Crew
7.2Comfort
6.9Entertainment
Airline reviews

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

8.0 ExcellentTaneca, Jan 2026
ROA - CLT
Read more American Airlines reviews

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

They should have allowed for extra time to de-ice the plane before boarding passengers. This delayed us about 10-15 mins after we boarded. Overall experience was fine. Crew was friendly and on top of everything. We didn’t have any issues during the flight.

Experience was good. We were delayed in leaving by 15 mins because the flight was waiting on a family that was late in getting to the gate. Food and drink options were as expected. I highly recommend checking in ahead of time using the airline’s app so that it’s quicker to get your luggage tags as soon as you arrive at the terminal. No more waiting in long lines!

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

We never made it due to delays on both ends. Gate attendant said it was mechanical but the system said otherwise, so no compensation. That’s not right.

Our flight from Eagle to Vail was delayed to the point we missed our connection to Savannah. Now we’re a family of 4 in a hotel room with luggage, no toiletries, no clean clothes. Gate attendant said the delay was mechanical but it was put in the system as something else so no compensation. That’s just wrong.

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

After the door had been closed, the cockpit makes an announcement that catering is running late and it is not the airline's fault. It is their fault in the sense that we had to sit for 2 hours or more when we could have stayed in the terminal. Poor communications between catering and airline. This caused a young man to lose his temper and he went storming out hitting objects. He had complained to the gate agent that he had already waited at the gate 7 hours and when can the airplane leave? Airilnes do a poor job of explaining delays, maintenance issues, etc. whereas being truthful may gain more sympathy or understanding.

The captain brought my 6 year old son into the cockpit and allowed him to ask questions, sit in the captain’s chair and talk about all the gears and levers. Made the trip very special for him.

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Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison