$163 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 6/9. 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
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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

Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
6:21 am - 9:20 pm
SJU
-
MSN
15h 59m
1 stop
American Airlines Logo
6:01 am - 11:00 pm
MSN
-
SJU
15h 59m
1 stop
$326American Airlines
Thu, May 28 - Sun, May 31
American Airlines Logo
6:20 am - 5:22 pm
SJU
-
MSN
12h 02m
1 stop
American Airlines Logo
7:00 am - 10:45 pm
MSN
-
SJU
14h 45m
1 stop
$334American Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
10:29 am - 9:20 pm
SJU
-
MSN
11h 51m
2 stops
American Airlines Logo
6:01 am - 11:00 pm
MSN
-
SJU
15h 59m
1 stop
$366American Airlines
Wed, May 27 - Sun, May 31
American Airlines Logo
6:20 am - 5:22 pm
SJU
-
MSN
12h 02m
1 stop
American Airlines Logo
7:00 am - 10:45 pm
MSN
-
SJU
14h 45m
1 stop
$375American Airlines
Wed, Jun 10 - Wed, Jun 24
JetBlue Logo
2:14 pm - 9:02 pm
SJU
-
MSN
7h 48m
1 stop
JetBlue Logo
5:52 am - 4:46 pm
MSN
-
SJU
9h 54m
1 stop
$396JetBlue
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
10:29 am - 9:20 pm
SJU
-
MSN
11h 51m
2 stops
American Airlines Logo
6:01 am - 11:00 pm
MSN
-
SJU
15h 59m
1 stop
$409American Airlines
Sun, Jul 26 - Sun, Aug 2
JetBlue Logo
2:42 pm - 10:38 pm
SJU
-
MSN
8h 56m
1 stop
JetBlue Logo
11:07 am - 8:45 pm
MSN
-
SJU
8h 38m
1 stop
$431JetBlue
Thu, Jul 9 - Sat, Jul 18
Multiple Airlines Logo
8:00 am - 8:25 am
SJU
-
MSN
25h 25m
1 stop
Multiple Airlines Logo
10:27 am - 4:05 pm
MSN
-
SJU
28h 38m
2 stops
$451Multiple Airlines
Mon, May 18 - Sun, May 31
American Airlines Logo
7:25 am - 11:54 pm
SJU
-
MSN
17h 29m
1 stop
American Airlines Logo
7:00 am - 10:45 pm
MSN
-
SJU
14h 45m
1 stop
$458American Airlines
Thu, May 28 - Sun, May 31
American Airlines Logo
2:56 pm - 11:59 pm
SJU
-
MSN
10h 03m
2 stops
American Airlines Logo
7:00 am - 10:45 pm
MSN
-
SJU
14h 45m
1 stop
$460American 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 $326 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $229 in the last 3 days.

Find deals

Good to know

Low seasonAugust
Cheapest flight$163
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 16% 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 $326 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $229 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 1,260 direct flights from within Puerto Rico to Madison. The most common day for departures is Sunday, with 16% 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 11666 reviews
7.2Comfort
7.5Boarding
7.9Crew
6.9Entertainment
6.4Food
Airline reviews

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

8.0 ExcellentConnie, May 2026
PHX - MKE
Read more American Airlines reviews

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Delayed due to weather in Dallas (arriving flight arrived late), then boarded the plane only to deboard immediately afterwards, tire needed to be replaced. Flight supposed to depart at 6:15pm but departed at 9:35pm.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

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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)