HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madison

$153+ Cheap flights from Caribbean 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
ago. 9 — ago. 161
sáb. 8/9
sáb. 8/16
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean to Madison with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Caribbean to Madison

Keep the following information in mind while searching for Caribbean to Madison flight deals. Data was last updated agosto 4, 2025.

Round-trip from

$297
(American Airlines)

One-way from

$153
(United Airlines)

Popular in

November

Cheapest in

August

Average price

$318
From Caribbean to Madison Truax Field
Search Deals
One-way flight from Caribbean 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).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Caribbean to Madison

Cheapest flights from Caribbean to Madison
Explore the most affordable flight options available from Caribbean to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 4, 2025.

This American Airlines deal was found by Cheapflights users on 8/2. 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.
jue. 8/218:00 amSJU - MSN
1 stop16h 59mAmerican Airlines
vie. 9/195:08 pmMSN - SJU
2 stops17h 03mAmerican Airlines
Deal found 8/2$297
This American Airlines deal was found by Cheapflights users on 8/2. 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.
jue. 10/301:00 pmMBJ - MSN
1 stop10h 01mAmerican Airlines
lun. 12/17:00 amMSN - MBJ
1 stop7h 01mAmerican Airlines
Deal found 8/2$469
This United Airlines deal was found by Cheapflights users on 8/4. 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.
jue. 8/71:25 pmSJU - MSN
1 stop8h 10mUnited Airlines
lun. 8/182:35 pmMSN - SJU
1 stop8h 19mUnited Airlines
Deal found 8/4$569

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 agosto 4, 2025.
Use the filters below to find and compare flights from Caribbean to Madison that are best for you.

Fly from

Caribbean

Fly to

Madison

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

jue. 8/21

8:00 am-11:59 pm

1 stop16h 59m

Madison Truax Field

vie. 9/19

5:08 pm-11:11 am

2 stops17h 03m

$297

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

jue. 10/30

1:00 pm-11:01 pm

1 stop10h 01m

Madison Truax Field

lun. 12/1

7:00 am-3:01 pm

1 stop7h 01m

$469

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

jue. 12/18

2:05 am-1:42 pm

2 stops13h 37m

Madison Truax Field

mié. 1/14

10:45 am-10:22 pm

2 stops9h 37m

$630

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

vie. 11/7

8:10 am-1:51 pm

1 stop7h 41m

$153

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

dom. 10/26

7:10 am-11:51 pm

1 stop17h 41m

$176

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

mié. 1/21

2:05 pm-10:38 pm

1 stop9h 33m

$293

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

mié. 1/21

11:50 am-9:16 pm

2 stops10h 26m

$302

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

mié. 1/21

1:12 pm-5:40 pm

3 stops29h 28m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/3

Best time to book a flight from Caribbean to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Caribbean 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 Caribbean to Madison

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

Currently, January is the cheapest month in which you can book a flight from Caribbean to Madison (average of $338). Flying from Caribbean 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 CB to MSN?

Find hourly flight availability from Caribbean 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 agosto 4, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean to Madison as you normally would.

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 agosto 4, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Caribbean 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.
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,987 reviews
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,912 reviews
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,987 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

Find useful and relevant information for your journey from Caribbean 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 Caribbean?

    If you book a flight to Madison from Caribbean, 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.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $153. American Airlines flights start at $176 while deals on Delta start at $293 one-way.

  • What are the most popular routes from Caribbean to Madison?

    The most popular route from Caribbean to Madison is San Juan Luis Munoz Marin Intl - Madison Truax Field. You may also consider Montego Bay Sangster Intl - Madison Truax Field or Nassau Intl - Madison Truax Field.

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

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

  • How can I find direct flights from Caribbean to Madison?

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 Caribbean to Madison?

    Currently, January is the cheapest month in which you can book a flight from Caribbean to Madison (average of $338). Flying from Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean to Madison

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Boston to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Denver to O'Hare Intl flights
Ontario to O'Hare Intl flights
Dallas/Fort Worth to Minneapolis flights
LaGuardia to Minneapolis flights
Sky Harbor Intl to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Austin to O'Hare Intl flights
Dulles Intl to Minneapolis flights
John F Kennedy Intl to Minneapolis flights
Newark to Minneapolis flights
Miami to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Burbank to O'Hare Intl flights
Portland to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Jose to O'Hare Intl flights
Love Field to O'Hare Intl flights
Baltimore to Minneapolis flights
Reagan-National to Minneapolis flights
Minneapolis to O'Hare Intl flights
Seattle to Minneapolis flights
Mexico City to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Hobby to O'Hare Intl flights
San Diego to O'Hare Intl flights
John F Kennedy Intl to Milwaukee flights
Boston to Minneapolis flights
Nashville to O'Hare Intl flights
LaGuardia to Milwaukee flights
Tampa to O'Hare Intl flights
Philadelphia to Minneapolis flights
Las Vegas to O'Hare Intl flights
Denver to Minneapolis flights
Newark to Milwaukee flights
San José to O'Hare Intl flights

Top airline flying from Caribbean to Madison

Discover the top airline that operate flights from Caribbean 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 agosto 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$513FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.