$221 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 1/9. 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
$295
Overall average: $582
American Airlines
Thu 1/29Sun 2/1
SJU - MSN • 2 stops
Cheapest one-way
$221
Typical prices: $281-$438
Multiple Airlines
Fri 1/9
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, Jan 29 - Sun, Feb 1
American Airlines Logo
5:51 pm - 10:11 amSJU-MSN
18h 20m2 stops
American Airlines Logo
5:22 pm - 12:30 pmMSN-SJU
17h 08m2 stops
$295American Airlines
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Wed, Dec 24 - Wed, Jan 7
American Airlines Logo
8:35 pm - 10:47 amSJU-MSN
16h 12m1 stop
American Airlines Logo
6:00 am - 6:22 pmMSN-SJU
10h 22m2 stops
$357American 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
8:10 am - 8:50 pmMSN-SJU
10h 40m1 stop
$382American Airlines
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Wed, Jan 28 - Sun, Feb 1
United Airlines Logo
2:05 am - 2:10 pmSJU-MSN
14h 05m2 stops
United Airlines Logo
2:56 pm - 6:11 amMSN-SJU
13h 15m2 stops
$440United Airlines
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Sat, Dec 20 - Fri, Jan 2
American Airlines Logo
8:25 am - 11:59 pmSJU-MSN
17h 34m1 stop
American Airlines Logo
8:10 pm - 5:00 amMSN-SJU
6h 50m1 stop
$480American 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
6:30 am - 3:40 pmMSN-SJU
7h 10m1 stop
$483United Airlines
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Sat, Dec 20 - Fri, Jan 2
American Airlines Logo
8:25 am - 11:59 pmSJU-MSN
17h 34m1 stop
American Airlines Logo
8:03 am - 9:11 pmMSN-SJU
11h 08m2 stops
$550American Airlines
Find Deal
Sat, Dec 20 - Fri, Jan 2
United Airlines Logo
4:52 pm - 10:30 pmSJU-MSN
7h 38m1 stop
United Airlines Logo
3:46 pm - 6:11 amMSN-SJU
12h 25m2 stops
$551United Airlines
Find Deal
Wed, Jan 28 - Sun, Feb 1
United Airlines Logo
2:05 am - 2:10 pmSJU-MSN
14h 05m2 stops
United Airlines Logo
8:15 am - 10:22 pmMSN-SJU
12h 07m2 stops
$555United Airlines
Find Deal
Wed, Jan 28 - Mon, Feb 2
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
$580United Airlines
Find Deal
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$221
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 514 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 11043 reviews
8.0Crew
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
Airline reviews

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

8.0 ExcellentWayne, Nov 2025MIA - BWI
Read more American Airlines reviews

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

I like how the crew and pilot kept us updated Even though our flight was slightly delayed. We made up time for it in the air. I really did enjoy my seat and amenities and my trip and value overall.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

The inflight staff is never the issue always the extra and charges american charges! Literally 30 bucks for WiFi! Is insane and then it’s choppy and slow. If you pay for it once you don’t need to pay again for switching aircraft especially when there is flight delays

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

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.

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Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison