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Cheap flights from Madison to Puerto Rico from $143

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Puerto Rico departing on 9/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Madison to Puerto Rico

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:43 am - 4:38 pm
MSN
-
SJU
9h 55m
1 stop
Delta Logo
2:59 pm - 10:41 pm
SJU
-
MSN
8h 42m
1 stop
$286Delta
Sun, Sep 6 - Wed, Sep 16
United Airlines Logo
10:40 am - 10:22 pm
MSN
-
SJU
9h 42m
2 stops
United Airlines Logo
8:05 am - 7:02 pm
SJU
-
MSN
12h 57m
2 stops
$301United Airlines
Tue, Nov 10 - Tue, Nov 17
United Airlines Logo
6:49 am - 2:44 pm
MSN
-
SJU
6h 55m
1 stop
United Airlines Logo
3:55 pm - 10:53 pm
SJU
-
MSN
7h 58m
1 stop
$304United Airlines
Mon, Oct 19 - Wed, Oct 28
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:00 am - 9:40 am
SJU
-
MSN
9h 40m
2 stops
$308United Airlines
Tue, Sep 8 - Thu, Sep 10
United Airlines Logo
10:40 am - 9:00 pm
MSN
-
SJU
8h 20m
1 stop
United Airlines Logo
8:25 am - 1:50 pm
SJU
-
MSN
7h 25m
1 stop
$336United Airlines
Tue, Nov 10 - Tue, Nov 17
American Airlines Logo
9:48 am - 11:15 pm
MSN
-
SJU
12h 27m
1 stop
American Airlines Logo
6:00 am - 3:51 pm
SJU
-
MSN
10h 51m
2 stops
$346American Airlines
Sun, Sep 6 - Wed, Sep 16
American Airlines Logo
8:05 pm - 3:40 pm
MSN
-
SJU
18h 35m
2 stops
American Airlines Logo
7:30 am - 9:21 pm
SJU
-
MSN
14h 51m
1 stop
$351American Airlines
Wed, Sep 30 - Mon, Oct 5
American Airlines Logo
1:25 pm - 10:24 pm
MSN
-
SJU
7h 59m
1 stop
American Airlines Logo
3:35 pm - 10:57 pm
SJU
-
MSN
8h 22m
1 stop
$371American Airlines
Tue, Sep 8 - Fri, Sep 11
Delta Logo
9:26 am - 11:50 pm
MSN
-
SJU
12h 24m
2 stops
Delta Logo
3:20 pm - 10:55 pm
SJU
-
MSN
9h 35m
1 stop
$386Delta
Sun, Jan 10 - Thu, Jan 14
American Airlines Logo
8:05 pm - 1:57 pm
MSN
-
SJU
16h 52m
2 stops
American Airlines Logo
6:20 am - 3:41 pm
SJU
-
MSN
10h 21m
2 stops
$391American Airlines
Wed, Sep 30 - Mon, Oct 5

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United Airlines flights from Madison to Puerto Rico

Our best United Airlines deals on Madison to Puerto Rico flight tickets
United Airlines
Nov 10
MSN10:40 amMadison Truax Field
9h 42m
2 stops
SJU10:22 pmSan Juan Luis Munoz Marin Intl
Nov 17
SJU8:05 amSan Juan Luis Munoz Marin Intl
12h 57m
2 stops
MSN7:02 pmMadison Truax Field
$301
United Airlines
Oct 19
MSN6:49 amMadison Truax Field
6h 55m
1 stop
SJU2:44 pmSan Juan Luis Munoz Marin Intl
Oct 28
SJU3:55 pmSan Juan Luis Munoz Marin Intl
7h 58m
1 stop
MSN10:53 pmMadison Truax Field
$304
United Airlines
Sep 8
MSN6:30 amMadison Truax Field
7h 14m
1 stop
SJU2:44 pmSan Juan Luis Munoz Marin Intl
Sep 10
SJU1:00 amSan Juan Luis Munoz Marin Intl
9h 40m
2 stops
MSN9:40 amMadison Truax Field
$308

American Airlines flights from Madison to Puerto Rico

Our best American Airlines deals on Madison to Puerto Rico flight tickets
American Airlines
Sep 6
MSN9:48 amMadison Truax Field
12h 27m
1 stop
SJU11:15 pmSan Juan Luis Munoz Marin Intl
Sep 16
SJU6:00 amSan Juan Luis Munoz Marin Intl
10h 51m
2 stops
MSN3:51 pmMadison Truax Field
$346
American Airlines
Sep 30
MSN8:05 pmMadison Truax Field
18h 35m
2 stops
SJU3:40 pmSan Juan Luis Munoz Marin Intl
Oct 5
SJU7:30 amSan Juan Luis Munoz Marin Intl
14h 51m
1 stop
MSN9:21 pmMadison Truax Field
$351
American Airlines
Sep 8
MSN1:25 pmMadison Truax Field
7h 59m
1 stop
SJU10:24 pmSan Juan Luis Munoz Marin Intl
Sep 11
SJU3:35 pmSan Juan Luis Munoz Marin Intl
8h 22m
1 stop
MSN10:57 pmMadison Truax Field
$371

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Puerto Rico 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, momondo users made 832,500 searches. Data last updated July 23, 2026.
Use the filters below to find and compare flights from Madison to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

5:43 am-4:38 pm

1 stop9h 55m

San Juan Luis Munoz Marin Intl

Wed 9/16

2:59 pm-10:41 pm

1 stop8h 42m

$286

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 11/10

10:40 am-10:22 pm

2 stops9h 42m

San Juan Luis Munoz Marin Intl

Tue 11/17

8:05 am-7:02 pm

2 stops12h 57m

$301
Quickest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 10/19

6:49 am-2:44 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Wed 10/28

3:55 pm-10:53 pm

1 stop7h 58m

$304

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 9/8

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Thu 9/10

1:00 am-9:40 am

2 stops9h 40m

$308

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 11/10

10:40 am-9:00 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Tue 11/17

8:25 am-1:50 pm

1 stop7h 25m

$336

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

9:48 am-11:15 pm

1 stop12h 27m

San Juan Luis Munoz Marin Intl

Wed 9/16

6:00 am-3:51 pm

2 stops10h 51m

$346

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 9/30

8:05 pm-3:40 pm

2 stops18h 35m

San Juan Luis Munoz Marin Intl

Mon 10/5

7:30 am-9:21 pm

1 stop14h 51m

$351

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 9/8

1:25 pm-10:24 pm

1 stop7h 59m

San Juan Luis Munoz Marin Intl

Fri 9/11

3:35 pm-10:57 pm

1 stop8h 22m

$371

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 1/10

9:26 am-11:50 pm

2 stops12h 24m

San Juan Luis Munoz Marin Intl

Thu 1/14

3:20 pm-10:55 pm

1 stop9h 35m

$386

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 9/30

8:05 pm-1:57 pm

2 stops16h 52m

San Juan Luis Munoz Marin Intl

Mon 10/5

6:20 am-3:41 pm

2 stops10h 21m

$391

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Puerto Rico from

How to get the cheapest flight ticket from Madison to Puerto Rico

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Puerto Rico?

If you don’t want to visit Puerto Rico in September, then you should wait until August to fly from Madison, when ticket prices are also cheap, with an average price of $366.

How far in advance should I book a flight from Madison to Puerto Rico?

You are more likely to see cheaper flights to Puerto Rico from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $516 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Madison for as low as $308 on momondo.

Can stopping save me money on Madison to Puerto Rico flights?

You could potentially save up to 40% on your flight if you consider stops on a Madison to Puerto Rico flight.

Cheap Madison to Puerto Rico flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Puerto Rico

Fastest flight time

7h 10m

Direct flights

None
The fastest flight from Madison to Puerto Rico takes 7h 10m
There are no direct flights from Madison to Puerto Rico. There are no popular flight routes from Madison to Puerto Rico.
Search flight deals

Frequently asked questions about flying from Madison to Puerto Rico

  • When did momondo last update prices for flights from Madison Truax Field Airport to Puerto Rico?

    Prices for flights from Madison Truax Field Airport to Puerto Rico refresh daily.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Puerto Rico?

  • How old do you have to be to fly from Madison Truax Field Airport to Puerto Rico?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Puerto Rico.

  • What documentation or ID do you need to fly to Puerto Rico?

    The required travel and health documents for your Puerto Rico trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Puerto Rico. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Madison to Puerto Rico

Compare and see reviews for airlines that fly from Madison to Puerto Rico with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $235Free CancellationRating
7.4
10,024 reviews
Search United Airlines flights
DeltaPriceFrom $246Free CancellationRating
7.8
8,479 reviews
Search Delta flights
American AirlinesPriceFrom $295Free CancellationRating
7.1
11,832 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Puerto Rico?

Finding the right flight to Puerto Rico from Madison is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Puerto Rico quick and easy, saving you time and money.

Can I find flights from Madison to Puerto Rico with flexible booking policies on momondo?

momondo does allow users to show only those flights to Puerto Rico from Madison which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Madison to Puerto Rico?

momondo provides multiple filters to help you find the best flight to Puerto Rico from Madison. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Madison to Puerto Rico right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Madison to Puerto Rico flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Puerto Rico trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Sat 8/22
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Find better results for your trip to Puerto Rico

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