Cheap Flights from Madison to San Juan

Compare Madison to San Juan flight deals

Find the cheapest month or even day of the year to fly to San Juan

Book the best San Juan fare with no extra fees

Flight deals from Madison to San Juan

Looking for a cheap last-minute deal or the best return flight from Madison Airport to San Juan? If you want to travel next month, return fares start from R 9,659. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Madison to San Juan

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Madison to San Juan flights are currently cheapest in July.

Madison to San Juan: Flight information

The things to know before you go.
Cheapest flight foundR 3,977
Cheapest month to flyJuly

Finding cheap flights from Madison to San Juan: Frequently asked questions

There are 6 airports in San Juan: San Juan Isla Grande, San Juan Luis Munoz Marin, Roosevelt Roads, Ponce, Vieques, and Culebra.
The best price we found for a return flight from Madison to San Juan is R 4,027. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Madison to San Juan. But we found flights with one or more stops from R 4,027.
As of May 2026, there are no flights flying from Madison to San Juan.
The cheapest month to fly from Madison to San Juan is usually September.
If you're flying from Madison Airport, the cheapest airport near San Juan is San Juan Luis Munoz Marin – which is 11.3 km away from the centre of San Juan. We've found flights into this airport from R 4,027.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Madison Airport to San Juan on Wednesday, 16 September 2026.
No airlines currently offer direct flights between Madison Airport and San Juan. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Juan but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Juan is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 27°C. August is typically the warmest month in San Juan, when it usually averages around 29°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging 23°C. The rainiest month is September.
Currently, United offers the cheapest flight tickets to San Juan.

Travelling from Dane County Regional Airport (MSN) to San Juan: what you need to know

  • San Juan is two hours ahead of Madison, where Dane County Regional Airport is located. San Juan observes the UTC-4 timezone.

  • Leave plenty of time to make your MSN to San Juan flight. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Travelling during a peak month like October? School holidays and other popular seasons can lead to longer lines at security. Play things extra safe and arrive up to four hours ahead of international flights and two hours before domestic departures.

  • We make it simple to book plane tickets from MSN to San Juan with a stopover. To see all the options, uncheck 'Direct flights only.' Then, select a flight that has a stop long enough to tour the city of your choice. Major stopovers include:

    • Chicago O'Hare International Airport (ORD)

    • Charlotte Douglas International Airport (CLT)

    • Philadelphia International Airport (PHL)

  • Travelling from central Madison to MSN takes about 40 minutes by public transport. If you drive, ride-share or grab a taxi, you'll cover the 10 kilometres in 20 minutes or so, depending on traffic conditions.

  • Have an early flight from Dane County Regional Airport to San Juan? Avoid the last-minute rush to the terminal (and sneak in some extra snooze time) by choosing one of these stays close to MSN:

  • When it comes to Dane County Regional Airport's on-time performance, data shows 75% of flights arrive within the expected time frame.

  • The address for MSN is 4000 International Lane.

How to find the cheapest flights from Dane County Regional Airport (MSN) to San Juan

  • R 3,977 is the cheapest price we've seen for a one-way Dane County Regional Airport to San Juan flight. A return plane ticket right now is R 4,027. Depending on how early you book and the availability, these fares can change.

  • Booking ahead of time is often the key to scoring a cheap flight from MSN to San Juan. Prices tend to rise as demand increases, so the closer you get to departure, the more it could cost you.

  • Scoring cheap tickets from Dane County Regional Airport to San Juan is more likely if you're flexible with your trip dates. Try using the 'Whole month' function to access the lowest prices across every month and walk away with an epic deal.

  • Never miss a deal on cheap flights from MSN to San Juan by creating a Price Alert. You'll receive an email or notification on the app when a special offer becomes available.

  • Save on your flight from Dane County Regional Airport to San Juan with the help of our filters. Select your preferred duration, departure time and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in San Juan

Luis Munoz Marin International Airport (SJU)

  • Luis Munoz Marin International Airport (SJU) is around 11 kilometres from central San Juan. If you're opting for a ride-share or a taxi, the drive takes roughly 20 minutes.

  • If you're taking public transport, expect a journey time of about 1 hour.

  • If you have a late flight from Dane County Regional Airport to San Juan, few things beat the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and resting not long after at one of these hotels near SJU:

  • Reserving your ride from Luis Munoz Marin International Airport about two weeks ahead of your flight from MSN to San Juan can help you secure the lowest rate.

Best time to go to San Juan

  • March is the most popular month for flights from Dane County Regional Airport to San Juan. To steer clear of the crowds, head to San Juan in December.

  • Before booking a Dane County Regional Airport to San Juan plane ticket, think about the kind of weather you prefer. August is the warmest month in San Juan, with temperatures ranging from 24ºC (75ºF) to 32ºC (90ºF).

  • If you want cooler conditions, search for a cheap ticket from MSN to San Juan in February when temperatures average between 21ºC (70ºF) and 28ºC (82ºF).

More about San Juan

  • Start your San Juan trip right by choosing the ideal place to stay. Once you've booked your flight from Dane County Regional Airport to San Juan, browse our selection of accommodation options including:

  • Esperanza Beach and Balneario El Escambron are just the start of the leading attractions to add to your San Juan to-do list. Keep the adventure rolling by checking out Escambron Green.

Explore more of Puerto Rico

  • Aguadilla is just one of the many places in Puerto Rico waiting to be discovered after you've seen San Juan. Around 113 kilometres away to the west, popular attractions include Silla Aguadilla, Bridges Surf Beach and Playa Rompe Olas.

  • If you're interested in discovering another major destination in Puerto Rico, head for Isabela, about 105 kilometres west of San Juan. Playa montones, Shore Island Beach and Guajataca Forest Reserve are highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.