$223 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 1/20. 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
$239
Overall average: $528
American Airlines
Thu 2/26Tue 3/3
SJU - MSN • 1 stop
Cheapest one-way
$223
Typical prices: $281-$438
Multiple Airlines
Tue 1/20
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

Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
6:00 am - 2:25 pm
SJU
-
MSN
10h 25m1 stop
American Airlines Logo
9:43 am - 9:33 pm
MSN
-
SJU
9h 50m2 stops
$239American Airlines
Fri, Jan 30 - Wed, Feb 4
American Airlines Logo
8:20 am - 6:44 pm
SJU
-
MSN
12h 24m2 stops
American Airlines Logo
7:25 am - 8:50 pm
MSN
-
SJU
11h 25m2 stops
$273American Airlines
Fri, Feb 20 - Wed, Feb 25
American Airlines Logo
7:00 am - 4:51 pm
SJU
-
MSN
11h 51m2 stops
American Airlines Logo
8:09 am - 8:36 pm
MSN
-
SJU
10h 27m2 stops
$303American Airlines
Wed, Apr 29 - Tue, May 5
American Airlines Logo
5:40 am - 10:29 pm
SJU
-
MSN
17h 49m1 stop
American Airlines Logo
6:27 am - 7:45 pm
MSN
-
SJU
12h 18m2 stops
$306American Airlines
Wed, Jan 28 - Sat, Jan 31
United Airlines Logo
8:35 am - 4:50 pm
SJU
-
MSN
10h 15m1 stop
United Airlines Logo
12:32 pm - 12:36 am
MSN
-
SJU
10h 04m2 stops
$325United Airlines
Fri, Jan 16 - Sat, Jan 24
Multiple Airlines Logo
6:25 am - 9:08 am
SJU
-
MSN
28h 43m1 stop
Multiple Airlines Logo
6:16 pm - 5:58 pm
MSN
-
SJU
21h 42m2 stops
$330Multiple Airlines
Fri, Jan 16 - Sat, Jan 24
American Airlines Logo
8:20 am - 11:41 pm
SJU
-
MSN
17h 21m1 stop
American Airlines Logo
11:23 am - 10:26 pm
MSN
-
SJU
9h 03m1 stop
$337American Airlines
Tue, Apr 28 - Tue, May 5
United Airlines Logo
1:00 am - 10:11 am
SJU
-
MSN
10h 11m2 stops
United Airlines Logo
8:23 am - 11:50 pm
MSN
-
SJU
14h 27m2 stops
$368United Airlines
Wed, Apr 8 - Tue, Apr 14
American Airlines Logo
11:59 pm - 10:31 am
SJU
-
MSN
11h 32m1 stop
American Airlines Logo
7:55 am - 7:55 pm
MSN
-
SJU
11h 00m2 stops
$389American Airlines
Fri, Jan 9 - Wed, Jan 14
Multiple Airlines Logo
7:04 pm - 9:08 am
SJU
-
MSN
16h 04m1 stop
Multiple Airlines Logo
6:16 pm - 11:35 pm
MSN
-
SJU
51h 19m2 stops
$415Multiple 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$223
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 534 direct flights from within Puerto Rico to Madison. The most common day for departures is Monday, 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 11054 reviews
8.0Crew
6.4Food
7.2Comfort
7.5Boarding
6.9Entertainment
Airline reviews

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

10.0 ExcellentPaul, Dec 2025
SEA - CLT
Read more American Airlines reviews

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

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.

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Everything you need to know for your flight to Madison

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