$115 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 4/22. 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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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, May 14 - Mon, May 18
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$287American Airlines
Fri, Apr 24 - Sat, May 16
American Airlines Logo
7:25 am - 11:55 pm
SJU
-
MSN
17h 30m
1 stop
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$291American Airlines
Fri, Apr 24 - Fri, May 15
United Airlines Logo
3:56 pm - 11:49 pm
SJU
-
MSN
8h 53m
1 stop
United Airlines Logo
8:10 am - 9:24 pm
MSN
-
SJU
12h 14m
2 stops
$313United Airlines
Fri, Apr 24 - Sat, May 16
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
9:18 am - 8:55 pm
MSN
-
SJU
10h 37m
2 stops
$319American Airlines
Fri, Apr 24 - Fri, May 15
American Airlines Logo
7:25 am - 11:55 pm
SJU
-
MSN
17h 30m
1 stop
American Airlines Logo
6:45 am - 8:51 pm
MSN
-
SJU
13h 06m
1 stop
$352American Airlines
Mon, May 4 - Sat, May 9
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$360American Airlines
Fri, Apr 24 - Sat, May 16
American Airlines Logo
1:31 pm - 11:55 pm
SJU
-
MSN
11h 24m
2 stops
American Airlines Logo
9:18 am - 8:55 pm
MSN
-
SJU
10h 37m
2 stops
$368American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
6:45 am - 9:24 pm
MSN
-
SJU
13h 39m
2 stops
$370American Airlines
Sat, Apr 25 - Fri, May 15
United Airlines Logo
7:40 am - 3:10 pm
SJU
-
MSN
8h 30m
1 stop
United Airlines Logo
8:10 am - 9:24 pm
MSN
-
SJU
12h 14m
2 stops
$403United Airlines
Thu, Apr 16 - Mon, Apr 20
United Airlines Logo
1:00 am - 1:51 pm
SJU
-
MSN
13h 51m
2 stops
United Airlines Logo
8:30 am - 9:24 pm
MSN
-
SJU
11h 54m
2 stops
$409United 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 flight to Madison?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Madison was found on the route from San Juan, at $287 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $189 in the last 3 days.

Good to know

Low seasonAugust
Cheapest flight$115
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from San Juan to Madison

FAQs - booking Madison flights

  • What is the cheapest flight to Madison?

    In the last 3 days, the cheapest flight deal to Madison was found on the route from San Juan, at $287 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $189 in the last 3 days.

  • 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 507 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.
7.1
American AirlinesOverall score based on 11403 reviews
7.5Boarding
8.0Crew
6.9Entertainment
7.2Comfort
6.4Food
Airline reviews

The crew was excellent and overall the flight was good. No complaints.

10.0 ExcellentMichelle, Mar 2026
DFW - LGA
Read more American Airlines reviews

The crew was excellent and overall the flight was good. No complaints.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

Never had such a lazy first class attendant. Literally spent 60%+ of the flight playing games on her personal phone making up excuses of why she was unavailable.

The flight attendants and the service is getting worse by the day.

Not to have gotten delayed by 2+ hours for the fourth straight American flight. They're the worst.

Like all of the flights I took to get down to Dallas. They were delayed

Other than nearly three hour delay for maintenance issues, everything went smooth

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

Meals were not so good. Snack between the meals was very bad. Like Japan Airlines, they could eliminate the snack and make the second meal much better.

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Everything you need to know for your flight to Madison

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