$181 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 2/28. 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
$275
Typical prices: $481-$574
American Airlines
Fri 2/6Tue 2/10
SJU - MSN • 1 stop
Cheapest one-way
$181
Typical prices: $194-$382
American Airlines
Sat 2/28
SJU - MSN • 1 stop
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
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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

Fri, Feb 6 - Tue, Feb 10
American Airlines Logo
6:00 am - 12:46 pm
SJU
-
MSN
8h 46m1 stop
American Airlines Logo
11:29 am - 9:39 pm
MSN
-
SJU
8h 10m1 stop
$275American Airlines
Fri, Feb 6 - Tue, Feb 10
United Airlines Logo
8:10 am - 7:07 pm
SJU
-
MSN
12h 57m2 stops
United Airlines Logo
6:30 am - 9:26 pm
MSN
-
SJU
12h 56m2 stops
$325United Airlines
Wed, Apr 29 - Tue, May 5
American Airlines Logo
5:40 am - 10:29 pm
SJU
-
MSN
17h 49m1 stop
American Airlines Logo
6:38 am - 7:45 pm
MSN
-
SJU
12h 07m2 stops
$339American Airlines
Tue, Dec 23 - Tue, Jan 6
American Airlines Logo
6:15 pm - 10:08 am
SJU
-
MSN
17h 53m1 stop
American Airlines Logo
4:30 pm - 12:30 pm
MSN
-
SJU
18h 00m2 stops
$350American Airlines
Wed, Jan 21 - Mon, Jan 26
United Airlines Logo
2:05 am - 2:52 pm
SJU
-
MSN
14h 47m2 stops
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m1 stop
$368United Airlines
Tue, Dec 23 - Tue, Jan 6
American Airlines Logo
6:00 am - 7:40 pm
SJU
-
MSN
15h 40m1 stop
American Airlines Logo
6:00 am - 9:39 pm
MSN
-
SJU
13h 39m1 stop
$380American Airlines
Tue, Dec 23 - Tue, Jan 6
American Airlines Logo
10:25 am - 7:40 pm
SJU
-
MSN
11h 15m2 stops
American Airlines Logo
4:30 pm - 12:30 pm
MSN
-
SJU
18h 00m2 stops
$390American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
3:15 pm - 11:02 pm
SJU
-
MSN
8h 47m1 stop
American Airlines Logo
3:33 pm - 4:00 am
MSN
-
SJU
11h 27m1 stop
$408American 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
$440United Airlines
Wed, Jan 21 - Mon, Jan 26
United Airlines Logo
2:05 am - 2:10 pm
SJU
-
MSN
14h 05m2 stops
United Airlines Logo
8:15 am - 12:36 am
MSN
-
SJU
14h 21m2 stops
$508United 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$181
Best time to beat the crowds but there is an average 11% 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 619 direct flights from within Puerto Rico to Madison. The most common day for departures is Tuesday, with 16% 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 11046 reviews
6.9Entertainment
7.2Comfort
7.5Boarding
8.0Crew
6.5Food
Airline reviews

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

2.0 MediocreJeremy, Dec 2025
CLT - GNV
Read more American Airlines reviews

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.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

Liked that it was on time. Staff professional and friendly.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

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Everything you need to know for your flight to Madison

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