$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 2/5. 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
$230
Overall average: $528
American Airlines
Sat 2/14Sat 2/14
SJU - MSN • 1 stop
Cheapest one-way
$118
Typical prices: $194-$382
United Airlines
Thu 2/5
SJU - MSN • 2 stops
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

Sat, Feb 14 - Sat, Feb 14
American Airlines Logo
6:33 am - 2:32 pm
SJU
-
MSN
9h 59m1 stop
American Airlines Logo
5:17 pm - 11:40 am
MSN
-
SJU
16h 23m1 stop
$230American Airlines
Sat, Feb 14 - Sat, Feb 14
American Airlines Logo
7:00 am - 3:20 pm
SJU
-
MSN
10h 20m2 stops
American Airlines Logo
8:22 pm - 5:24 am
MSN
-
SJU
7h 02m1 stop
$268American Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 2:07 pm
SJU
-
MSN
14h 02m2 stops
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m2 stops
$325United Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 11:53 am
SJU
-
MSN
11h 48m2 stops
United Airlines Logo
2:48 pm - 6:11 am
MSN
-
SJU
13h 23m2 stops
$368United Airlines
Tue, Jan 13 - Sat, Jan 17
Multiple Airlines Logo
3:47 pm - 9:08 am
SJU
-
MSN
19h 21m1 stop
Multiple Airlines Logo
6:16 pm - 12:32 pm
MSN
-
SJU
16h 16m2 stops
$382Multiple Airlines
Tue, Jan 13 - Sat, Jan 17
United Airlines Logo
7:45 am - 4:44 pm
SJU
-
MSN
10h 59m2 stops
United Airlines Logo
12:32 pm - 12:36 am
MSN
-
SJU
10h 04m2 stops
$399United Airlines
Tue, Jan 20 - Fri, Jan 30
United Airlines Logo
8:35 am - 4:44 pm
SJU
-
MSN
10h 09m1 stop
United Airlines Logo
3:48 pm - 6:11 am
MSN
-
SJU
12h 23m2 stops
$417United Airlines
Tue, Jan 20 - Fri, Jan 30
American Airlines Logo
6:00 am - 6:44 pm
SJU
-
MSN
14h 44m1 stop
American Airlines Logo
11:29 am - 9:39 pm
MSN
-
SJU
8h 10m1 stop
$420American Airlines
Fri, Feb 13 - Sat, Feb 14
United Airlines Logo
2:05 am - 11:53 am
SJU
-
MSN
11h 48m2 stops
United Airlines Logo
2:48 pm - 6:11 am
MSN
-
SJU
13h 23m2 stops
$450United 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 - 9:00 pm
MSN
-
SJU
28h 12m1 stop
$475United 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.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$118
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.

  • 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 320 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 11074 reviews
6.4Food
7.2Comfort
8.0Crew
7.5Boarding
6.9Entertainment
Airline reviews

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.

10.0 ExcellentAnonymous, Dec 2025
PHX - CMH
Read more American Airlines reviews

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.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Original flight was canceled and rescheduled for the next day. Cancelation notice was sent in the middle of the night (only saw it in the morning), leaving no room to find other options. No offers to reimburse for the extra expenses or compensations. My flight to Rio on 12/12 was also delayed for 16 hours. This seems to be the new normal for AA.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

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

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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)