$158 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 10/23. 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, Aug 21 - Thu, Aug 27
American Airlines Logo
3:28 pm - 11:59 pm
SJU
-
MSN
9h 31m
2 stops
American Airlines Logo
6:00 am - 12:15 am
MSN
-
SJU
17h 15m
1 stop
$333American Airlines
Fri, Aug 21 - Thu, Aug 27
American Airlines Logo
1:38 pm - 11:59 pm
SJU
-
MSN
11h 21m
2 stops
American Airlines Logo
9:48 am - 12:15 am
MSN
-
SJU
13h 27m
2 stops
$374American Airlines
Thu, Aug 6 - Mon, Aug 10
Delta Logo
7:30 am - 9:19 pm
SJU
-
MSN
14h 49m
2 stops
Delta Logo
5:43 am - 4:38 pm
MSN
-
SJU
9h 55m
1 stop
$378Delta
Thu, Jun 18 - Sun, Jun 21
JetBlue Logo
12:54 pm - 10:43 pm
SJU
-
MSN
10h 49m
1 stop
JetBlue Logo
11:07 am - 10:27 pm
MSN
-
SJU
10h 20m
1 stop
$381JetBlue
Sat, Jun 27 - Sun, Jul 5
American Airlines Logo
6:21 am - 10:31 pm
SJU
-
MSN
17h 10m
1 stop
American Airlines Logo
7:00 am - 10:59 pm
MSN
-
SJU
14h 59m
1 stop
$401American Airlines
Tue, Jul 7 - Tue, Jul 14
American Airlines Logo
7:25 am - 11:42 pm
SJU
-
MSN
17h 17m
1 stop
American Airlines Logo
6:00 am - 10:57 pm
MSN
-
SJU
15h 57m
1 stop
$406American 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
$416JetBlue
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
1:38 pm - 11:46 pm
SJU
-
MSN
11h 08m
2 stops
American Airlines Logo
6:01 am - 6:34 pm
MSN
-
SJU
11h 33m
2 stops
$459American Airlines
Tue, Jul 21 - Sat, Jul 25
Multiple Airlines Logo
6:00 am - 9:47 am
SJU
-
MSN
28h 47m
2 stops
Multiple Airlines Logo
7:55 pm - 7:57 am
MSN
-
SJU
11h 02m
1 stop
$472Multiple Airlines
Wed, Jun 17 - Tue, Jun 23
American Airlines Logo
11:56 am - 12:09 am
SJU
-
MSN
13h 13m
2 stops
American Airlines Logo
6:01 am - 11:00 pm
MSN
-
SJU
15h 59m
1 stop
$489American 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 3 days.

In the last 3 days, the cheapest flight deal to Madison was found on the route from San Juan, at $333 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $260 in the last 3 days.

Good to know

Low seasonAugust
Cheapest flight$158
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 $333 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $260 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 1,028 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.
7.1
American AirlinesOverall score based on 11639 reviews
7.5Boarding
7.2Comfort
7.9Crew
6.9Entertainment
6.4Food
Airline reviews

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

10.0 ExcellentIngrid, May 2026
ONT - DFW
Read more American Airlines reviews

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

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