$118 Find Cheap Flights from Puerto Rico to Madison

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight to Madison departing on 1/28. 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
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
$235
Overall average: $582
United Airlines
Wed 1/28Mon 2/2
SJU - MSN • 1 stop
Cheapest one-way
$776
Typical prices: $281-$438
United Airlines
Fri 1/2
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

Wed, Jan 28 - Mon, Feb 2
United Airlines Logo
8:35 am - 2:52 pmSJU-MSN
8h 17m1 stop
United Airlines Logo
6:30 am - 3:40 pmMSN-SJU
7h 10m1 stop
$235United Airlines
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Wed, Jan 28 - Sun, Feb 1
American Airlines Logo
6:00 am - 4:52 pmSJU-MSN
12h 52m1 stop
American Airlines Logo
6:00 am - 9:39 pmMSN-SJU
13h 39m1 stop
$268American Airlines
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Tue, Jan 27 - Mon, Feb 2
United Airlines Logo
2:05 am - 12:03 pmSJU-MSN
11h 58m2 stops
United Airlines Logo
8:15 am - 10:22 pmMSN-SJU
12h 07m2 stops
$277United Airlines
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Thu, Jan 29 - Sun, Feb 1
American Airlines Logo
1:24 pm - 11:41 pmSJU-MSN
12h 17m2 stops
American Airlines Logo
3:57 pm - 10:48 amMSN-SJU
16h 51m2 stops
$295American Airlines
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Tue, Jan 27 - Sun, Feb 1
United Airlines Logo
2:05 am - 2:10 pmSJU-MSN
14h 05m2 stops
United Airlines Logo
6:30 am - 9:26 pmMSN-SJU
12h 56m2 stops
$325United Airlines
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Thu, Feb 12 - Tue, Feb 17
American Airlines Logo
6:00 am - 4:42 pmSJU-MSN
12h 42m1 stop
American Airlines Logo
10:58 am - 8:36 pmMSN-SJU
7h 38m1 stop
$350American Airlines
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Wed, Dec 24 - Wed, Jan 7
American Airlines Logo
5:24 am - 4:49 pmSJU-MSN
13h 25m2 stops
American Airlines Logo
5:22 pm - 10:48 amMSN-SJU
15h 26m2 stops
$357American Airlines
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Wed, Jan 28 - Sun, Feb 1
United Airlines Logo
2:05 am - 12:03 pmSJU-MSN
11h 58m2 stops
United Airlines Logo
2:56 pm - 6:11 amMSN-SJU
13h 15m2 stops
$368United Airlines
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Thu, Jan 29 - Sun, Feb 1
American Airlines Logo
7:07 am - 9:11 pmSJU-MSN
16h 04m1 stop
American Airlines Logo
7:30 am - 9:39 pmMSN-SJU
12h 09m1 stop
$382American Airlines
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Mon, Feb 23 - Sat, Feb 28
United Airlines Logo
8:35 am - 3:02 pmSJU-MSN
8h 27m1 stop
United Airlines Logo
2:48 pm - 6:11 amMSN-SJU
13h 23m2 stops
$402United Airlines
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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$235
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 1% 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 567 direct flights from within Puerto Rico to Madison. The most common day for departures is Monday, with 17% 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
7.5Boarding
7.2Comfort
8.0Crew
6.4Food
6.9Entertainment
Airline reviews

I had a positive experience on American. I'm blind and traveling with a guide dog and the flight attendants were so kind, friendly, and helpful towards us. They checked in on us during the flight and they made us feel comfortable and welcomed. There was an hour delay before depature, but overall the flight was a smooth ride. I appreciate that there were no issues on this long flight back home.

8.0 ExcellentShirley, Nov 2025ILM - CLT
Read more American Airlines reviews

I had a positive experience on American. I'm blind and traveling with a guide dog and the flight attendants were so kind, friendly, and helpful towards us. They checked in on us during the flight and they made us feel comfortable and welcomed. There was an hour delay before depature, but overall the flight was a smooth ride. I appreciate that there were no issues on this long flight back home.

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

flight was good until we arrived at cmh ten minutes early but then sat on tarmac for twenty minutes because a plane was at our gate, so we had to wait despite the pilot tellling us that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

Traveling to a place near Madison?

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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)