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$181+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap 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 December 8, 2025.

This American Airlines deal was found by Cheapflights users on 12/7. 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.
Sat 12/276:00 amSJU - MSN
1 stop15h 40mAmerican Airlines
Wed 1/711:29 amMSN - SJU
1 stop8h 10mAmerican Airlines
Deal found 12/7$557
This United Airlines deal was found by Cheapflights users on 12/7. 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.
Mon 12/224:52 pmSJU - MSN
1 stop7h 38mUnited Airlines
Fri 12/265:26 pmMSN - SJU
2 stops10h 45mUnited Airlines
Deal found 12/7$708
This United Airlines deal was found by Cheapflights users on 12/7. 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.
Sat 12/277:45 amSJU - MSN
2 stops16h 45mUnited Airlines
Wed 1/712:32 pmMSN - SJU
2 stops10h 04mUnited Airlines
Deal found 12/7$753
This American Airlines deal was found by Cheapflights users on 12/7. 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.
Mon 12/226:44 amSJU - MSN
1 stop12h 16mAmerican Airlines
Fri 12/268:10 pmMSN - SJU
1 stop6h 50mAmerican Airlines
Deal found 12/7$784

Find 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 December 8, 2025.

Round-trip from

$275
(American Airlines)

One-way from

$181
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$461
From San Juan to Madison Truax Field
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One-way flight from San Juan to Madison Truax Field
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Highest demand for flights based on searches. 17% potential increase in price ($97 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 8, 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

Fri 2/6

6:00 am-12:46 pm

1 stop8h 46m

Madison Truax Field

Tue 2/10

11:29 am-9:39 pm

1 stop8h 10m

$275

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/29

5:40 am-10:29 pm

1 stop17h 49m

Madison Truax Field

Tue 5/5

3:33 pm-4:00 am

1 stop11h 27m

$277

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 2/6

8:10 am-7:07 pm

2 stops12h 57m

Madison Truax Field

Tue 2/10

6:30 am-9:26 pm

2 stops12h 56m

$325

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 4/28

1:00 am-1:59 pm

2 stops13h 59m

Madison Truax Field

Tue 5/5

6:30 am-9:24 pm

2 stops13h 54m

$368

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 1/21

2:05 am-2:10 pm

2 stops14h 05m

Madison Truax Field

Mon 1/26

6:30 am-3:40 pm

1 stop7h 10m

$368

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 5/7

11:45 am-11:02 pm

2 stops12h 17m

Madison Truax Field

Tue 5/12

11:28 am-4:00 am

1 stop15h 32m

$408

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sat 2/28

6:00 am-4:40 pm

1 stop12h 40m

$181

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 2/27

2:05 am-2:07 pm

2 stops14h 02m

$195

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 12/18

2:15 pm-10:57 pm

1 stop10h 42m

$245

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sat 4/4

7:00 am-5:14 pm

3 stops35h 14m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 12 results
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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, September is the cheapest month in which you can book a flight from San Juan to Madison (average of $113). Flying from San Juan to Madison in July is currently the most expensive (average of $289). 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 December 8, 2025.

It’s optimal to fly from San Juan to Madison in the evening. By choosing this option you can save up to 39% 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 December 8, 2025.
See what other customers who have flown with 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.
American Airlines
7.2
Good
11,042 reviews

Comfort

7.2

Crew

8.0

Overall

7.2

Entertainment

6.9

Food

6.5

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,042 reviews
American Airlines
7.2
Good
11,042 reviews

Comfort

7.2

Crew

8.0

Overall

7.2

Entertainment

6.9

Food

6.5

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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.

  • How long is the flight from San Juan to Madison?

    Airlines like American Airlines and United Airlines fly from San Juan to Madison in about 8h 46m. The time it takes to get you to your destination can typically vary by up to 4h 11m. The distance from San Juan to Madison is about 2180 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from San Juan to Madison round-trip?

    According to our current data, American Airlines ($265), offers the cheapest pricing from San Juan to Madison. You may be able to fly from San Juan to Madison for 43% less than the average price by searching for this airline.

  • What are the cheapest airlines to fly from San Juan to Madison one-way?

    One-way options have recently been found by users for as low as $112 on Delta. Other airlines that offer cheap prices include American Airlines from $132 and United Airlines from $140 one-way.

  • 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, September is the cheapest month in which you can book a flight from San Juan to Madison (average of $113). Flying from San Juan to Madison in July is currently the most expensive (average of $289). 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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$510FlexibilityNo cancel feeOn-time71%

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