$128 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 4/14. 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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$346
Overall average: $528
United Airlines
Tue 2/24Sat 2/28
SJU - MSN • 2 stops
Cheapest one-way
$128
Typical prices: $185-$390
United Airlines
Tue 4/14
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
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

Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 2:57 pm
SJU
-
MSN
14h 52m
2 stops
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$346United Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m
1 stop
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$389United Airlines
Sat, Jan 31 - Mon, Feb 2
American Airlines Logo
8:20 am - 6:55 pm
SJU
-
MSN
12h 35m
2 stops
American Airlines Logo
7:25 am - 8:50 pm
MSN
-
SJU
11h 25m
2 stops
$420American Airlines
Tue, Feb 10 - Sun, Feb 15
United Airlines Logo
2:05 am - 11:51 am
SJU
-
MSN
11h 46m
2 stops
United Airlines Logo
8:15 am - 10:22 pm
MSN
-
SJU
12h 07m
2 stops
$455United Airlines
Sat, Jan 31 - Mon, Feb 2
United Airlines Logo
8:35 am - 3:05 pm
SJU
-
MSN
8h 30m
1 stop
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m
1 stop
$534United 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 $566 respectively. For return trips, the best month to travel is September with an average price of $285.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$128
Best time to beat the crowds but there is an average 7% 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 428 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 11206 reviews
7.5Boarding
8.0Crew
6.4Food
6.9Entertainment
7.2Comfort
Airline reviews

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

4.0 OkayAllison, Jan 2026
MKE - DFW
Read more American Airlines reviews

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

We were upgraded to Business Class. So comfortable with great service and food options

The flight attendant use 1.5 hours to answer my call. My dirty food tray was unattended.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

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Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

Madison (MSN)