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Madison

$383+ Cheap flights from Jamaica 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MSN
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Jamaica to Madison

Keep the following information in mind while searching for Jamaica to Madison flight deals. Data was last updated September 15, 2025.

Round-trip from

$502
(United Airlines)

One-way from

$383
(Delta)
From Jamaica to Madison Truax Field
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One-way flight from Jamaica to Madison Truax Field
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Find flight deals from Jamaica to Madison

Cheapest flights from Jamaica to Madison
Explore the most affordable flight options available from Jamaica to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/301:50 pmMBJ - MSN
1 stop8h 13mAmerican Airlines
Mon 12/15:00 amMSN - MBJ
1 stop9h 28mAmerican Airlines
Deal found 9/14$502

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica 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 September 15, 2025.
Use the filters below to find and compare flights from Jamaica to Madison that are best for you.

Fly from

Jamaica

Fly to

Madison

Route

Depart

Return

Price

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 10/30

1:00 pm-11:01 pm

1 stop10h 01m

Madison Truax Field

Mon 12/1

5:00 am-3:28 pm

1 stop9h 28m

$502

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 1/1

8:00 am-9:20 pm

1 stop14h 20m

$383

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 1/1

6:05 pm-10:05 am

2 stops17h 00m

$446

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 1/1

5:14 pm-4:45 pm

2 stops24h 31m

$483

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Best time to book a flight from Jamaica to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Jamaica 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 Jamaica to Madison
No data available for this route at this time. Please check back soon.

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 September 15, 2025.
Read through reviews of airlines operating flights from Jamaica to Madison, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Entertainment

6.9

Comfort

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Entertainment

6.9

Comfort

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

Related info for your journey

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

    If you book a flight to Madison from Jamaica, 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.

  • How long is the flight from Jamaica to Madison?

    There are many flights that can get you from Jamaica to Madison in 10h 01m. Fly via American Airlines to get the fastest option. The distance from Jamaica to Madison is about 1826 mi.

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

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

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

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

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

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

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

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Baraboo
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Top airline flying from Jamaica to Madison

Discover the top airline that operate flights from Jamaica 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$436Average$502FlexibilityNo cancel feeOn-time71%

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