$203 Find Cheap Flights from Puerto Rico to Madison - Compare and Save

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 12/5. 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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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, Sep 17 - Mon, Sep 21
Delta Logo
7:00 am - 9:15 pm
SJU
-
MSN
15h 15m
2 stops
Delta Logo
6:00 am - 1:16 pm
MSN
-
SJU
6h 16m
1 stop
$256Delta
Thu, Aug 20 - Thu, Sep 3
American Airlines Logo
3:47 pm - 11:09 pm
SJU
-
MSN
8h 22m
1 stop
American Airlines Logo
6:00 am - 10:24 pm
MSN
-
SJU
15h 24m
1 stop
$336American Airlines
Mon, Sep 14 - Tue, Sep 22
Multiple Airlines Logo
6:31 pm - 4:00 pm
SJU
-
MSN
22h 29m
1 stop
Multiple Airlines Logo
4:40 pm - 1:50 am
MSN
-
SJU
8h 10m
1 stop
$341Multiple Airlines
Thu, Sep 17 - Mon, Sep 21
Delta Logo
7:30 am - 4:18 pm
SJU
-
MSN
9h 48m
1 stop
Delta Logo
6:00 am - 1:16 pm
MSN
-
SJU
6h 16m
1 stop
$357Delta
Mon, Sep 14 - Tue, Sep 22
American Airlines Logo
10:16 am - 7:46 pm
SJU
-
MSN
10h 30m
2 stops
American Airlines Logo
8:05 pm - 2:50 pm
MSN
-
SJU
17h 45m
2 stops
$366American Airlines
Thu, Aug 20 - Thu, Sep 3
American Airlines Logo
6:00 am - 3:33 pm
SJU
-
MSN
10h 33m
2 stops
American Airlines Logo
6:30 am - 11:59 pm
MSN
-
SJU
16h 29m
1 stop
$376American Airlines
Wed, Sep 30 - Sat, Oct 3
United Airlines Logo
3:56 pm - 10:35 pm
SJU
-
MSN
7h 39m
1 stop
United Airlines Logo
5:00 am - 2:44 pm
MSN
-
SJU
8h 44m
1 stop
$381United Airlines
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
7:00 am - 9:41 pm
SJU
-
MSN
15h 41m
1 stop
American Airlines Logo
7:00 am - 10:59 pm
MSN
-
SJU
14h 59m
1 stop
$406American Airlines
Mon, Sep 14 - Mon, Oct 19
American Airlines Logo
2:22 pm - 11:24 pm
SJU
-
MSN
10h 02m
1 stop
American Airlines Logo
8:25 pm - 1:45 pm
MSN
-
SJU
16h 20m
1 stop
$409American Airlines
Thu, Aug 20 - Thu, Sep 3
American Airlines Logo
6:00 am - 3:33 pm
SJU
-
MSN
10h 33m
2 stops
American Airlines Logo
6:00 am - 6:34 pm
MSN
-
SJU
11h 34m
2 stops
$416American 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 are the most popular airlines flying to Madison?

The most popular airline among KAYAK users flying to Madison is American Airlines, followed by Delta and Southwest.

Good to know

Low seasonAugust
Cheapest flight$203
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 15% 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 956 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 11703 reviews
6.8Entertainment
6.4Food
7.2Comfort
7.5Boarding
7.9Crew
Airline reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

6.0 GoodHardin, Jun 2026
ICT - ORD
Read more American Airlines reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

Check in for 5am flight at RDU was hampered by American check in counters being seriously understaffed , was told even supervisor called out. Took so long in line for special services check in that we missed our 5am departure even after arriving at 3:30am. Had to be rescheduled to later flight from Charlotte to St Thomas.

Delayed flight due to maintenance and I have had multiple delayed flights due to maintenance in the last month plus

Excellent service. Flight attendance like Jessica,, on our flight, is a reason I wouldn’t mind flying through British Airways again. Jessica,, was very courteous and helpful.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

Significant delays on my trip to Chicago and my trip back to NY

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Flight had mechanical issues and it was delayed 30 mins - some of us boarded and then had to deplane.

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Everything you need to know for your flight to Madison

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