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Madison

$183+ Cheap flights from San Juan to Madison (MSN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from San Juan to Madison

Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 30, 2025.

Round-trip from

$215
(American Airlines)

Popular in

November

Cheapest in

August

Average price

$616
From San Juan to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from San Juan to Madison

Cheapest flights from San Juan to Madison
Explore the most affordable flight options available from San Juan to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/244:43 pmSJU - MSN
2 stops18h 16mAmerican Airlines
Mon 9/296:40 pmMSN - SJU
2 stops17h 07mAmerican Airlines
Deal found 7/30$255
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/231:05 amSJU - MSN
2 stops9h 43mUnited Airlines
Mon 9/296:30 amMSN - SJU
1 stop7h 14mUnited Airlines
Deal found 7/30$385

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Juan to Madison that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2025.
Use the filters below to find and compare flights from San Juan to Madison that are best for you.

Fly from

San Juan

Fly to

Madison

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 9/24

4:43 pm-9:59 am

2 stops18h 16m

Madison Truax Field

Mon 9/29

6:40 pm-12:47 pm

2 stops17h 07m

$255

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 9/23

1:05 am-9:48 am

2 stops9h 43m

Madison Truax Field

Mon 9/29

6:30 am-2:44 pm

1 stop7h 14m

$385

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 11/7

8:10 am-1:51 pm

1 stop7h 41m

$183

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 8/8

6:00 am-7:44 pm

2 stops14h 44m

$228

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 8/7

2:40 am-8:01 am

3 stops30h 21m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from San Juan to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from San Juan with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Juan to Madison

What is the cheapest month to book a flight from San Juan to Madison?

Currently, January is the cheapest month in which you can book a flight from San Juan to Madison (average of $338). Flying from San Juan to Madison in March is currently the most expensive (average of $422). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SJU to MSN?

Find hourly flight availability from San Juan to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

It’s optimal to fly from San Juan to Madison in the morning. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the afternoon.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madison. Reviews last updated July 30, 2025.
See what other customers who have flown with United Airlines and American Airlines from San Juan to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,896 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
United Airlines
7.4
Good
8,896 reviews
United Airlines
7.4
Good
8,896 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,896 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Related info for your journey

Find useful and relevant information for your journey from San Juan to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Madison from San Juan?

    If you book a flight to Madison from San Juan, you will be flying to Truax Field, which is the city’s only airport. Madison Truax Field (MSN) is located 5.4 mi from the center of Madison. There are 0 flights from San Juan to Truax Field per day from 1 airline.

  • What are the cheapest airlines flying from San Juan to Madison round-trip?

    According to our current data, American Airlines ($215), and United Airlines ($385) offers the cheapest pricing from San Juan to Madison. You may be able to fly from San Juan to Madison for 60% less than the average price by searching for these airlines.

  • Can I find deals for flights from San Juan to Madison that include hotel bookings?

    Yes. In addition to deals on San Juan to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Juan to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Juan to Madison.

  • Can I find deals for business class flights from San Juan to Madison?

    Yes. Cheapflights offers flight deals from San Juan to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Juan to Madison?

    Currently, January is the cheapest month in which you can book a flight from San Juan to Madison (average of $338). Flying from San Juan to Madison in March is currently the most expensive (average of $422). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Top airline flying from San Juan to Madison

Discover the top airline that operate flights from San Juan to Madison. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$524FlexibilityNo cancel feeOn-time71%

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