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Cheap flights from Madison to Jamaica from $157

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 Jamaica departing on 8/22. 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 Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
3:55 pm - 10:13 am
MSN
-
MBJ
17h 18m
2 stops
American Airlines Logo
11:13 am - 9:56 pm
MBJ
-
MSN
11h 43m
2 stops
$362American Airlines
Fri, Dec 4 - Thu, Dec 10
American Airlines Logo
3:55 pm - 10:12 am
MSN
-
MBJ
17h 17m
1 stop
American Airlines Logo
2:30 pm - 9:19 am
MBJ
-
MSN
19h 49m
1 stop
$363American Airlines
Fri, Dec 4 - Thu, Dec 10
American Airlines Logo
5:00 am - 1:12 pm
MSN
-
MBJ
8h 12m
1 stop
American Airlines Logo
5:16 pm - 12:26 pm
MBJ
-
MSN
19h 10m
2 stops
$367American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
3:55 pm - 10:12 am
MSN
-
MBJ
17h 17m
1 stop
American Airlines Logo
2:30 pm - 9:19 am
MBJ
-
MSN
19h 49m
1 stop
$368American Airlines
Fri, Dec 4 - Thu, Dec 10
American Airlines Logo
3:55 pm - 10:13 am
MSN
-
MBJ
17h 18m
2 stops
American Airlines Logo
3:12 pm - 9:19 am
MBJ
-
MSN
19h 07m
1 stop
$372American Airlines
Fri, Dec 4 - Thu, Dec 10
United Airlines Logo
5:00 am - 4:12 pm
MSN
-
MBJ
10h 12m
2 stops
United Airlines Logo
5:14 pm - 9:53 am
MBJ
-
MSN
17h 39m
2 stops
$400United Airlines
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
3:55 pm - 10:12 am
MSN
-
MBJ
17h 17m
1 stop
American Airlines Logo
2:30 pm - 11:26 pm
MBJ
-
MSN
9h 56m
1 stop
$461American Airlines
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
5:00 am - 1:12 pm
MSN
-
MBJ
8h 12m
1 stop
American Airlines Logo
2:09 pm - 8:50 pm
MBJ
-
MSN
6h 41m
1 stop
$466American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
3:55 pm - 10:13 am
MSN
-
MBJ
17h 18m
2 stops
American Airlines Logo
2:02 pm - 11:49 pm
MBJ
-
MSN
10h 47m
2 stops
$471American Airlines
Fri, Dec 4 - Thu, Dec 10
United Airlines Logo
6:45 am - 4:12 pm
MSN
-
MBJ
32h 27m
2 stops
United Airlines Logo
3:36 pm - 12:12 am
MBJ
-
MSN
33h 36m
2 stops
$507United Airlines
Fri, Dec 4 - Thu, Dec 10

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United Airlines flights from Madison to Jamaica

Our best United Airlines deals on Madison to Jamaica flight tickets
United Airlines
Dec 5
MSN5:00 amMadison Truax Field
10h 12m
2 stops
MBJ4:12 pmMontego Bay Sangster Intl
Dec 12
MBJ5:14 pmMontego Bay Sangster Intl
17h 39m
2 stops
MSN9:53 amMadison Truax Field
$400
United Airlines
Dec 4
MSN6:45 amMadison Truax Field
32h 27m
2 stops
MBJ4:12 pmMontego Bay Sangster Intl
Dec 10
MBJ3:36 pmMontego Bay Sangster Intl
33h 36m
2 stops
MSN12:12 amMadison Truax Field
$507
United Airlines
Sep 21
MSN8:05 amMadison Truax Field
27h 38m
2 stops
MBJ11:43 amMontego Bay Sangster Intl
Sep 25
MBJ12:52 pmMontego Bay Sangster Intl
24h 45m
2 stops
MSN1:37 pmMadison Truax Field
$571

American Airlines flights from Madison to Jamaica

Our best American Airlines deals on Madison to Jamaica flight tickets
American Airlines
Dec 4
MSN3:55 pmMadison Truax Field
17h 18m
2 stops
MBJ10:13 amMontego Bay Sangster Intl
Dec 10
MBJ11:13 amMontego Bay Sangster Intl
11h 43m
2 stops
MSN9:56 pmMadison Truax Field
$362
American Airlines
Dec 4
MSN3:55 pmMadison Truax Field
17h 17m
1 stop
MBJ10:12 amMontego Bay Sangster Intl
Dec 10
MBJ2:30 pmMontego Bay Sangster Intl
19h 49m
1 stop
MSN9:19 amMadison Truax Field
$363
American Airlines
Sep 5
MSN6:53 pmMadison Truax Field
18h 56m
2 stops
MBJ1:49 pmMontego Bay Sangster Intl
Sep 12
MBJ5:16 pmMontego Bay Sangster Intl
19h 10m
2 stops
MSN12:26 pmMadison Truax Field
$367

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Jamaica 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 June 13, 2026.
Use the filters below to find and compare flights from Madison to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

3:55 pm-10:13 am

2 stops17h 18m

Montego Bay Sangster Intl

Thu 12/10

11:13 am-9:56 pm

2 stops11h 43m

$362

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

3:55 pm-10:12 am

1 stop17h 17m

Montego Bay Sangster Intl

Thu 12/10

2:30 pm-9:19 am

1 stop19h 49m

$363

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 9/5

5:00 am-1:12 pm

1 stop8h 12m

Montego Bay Sangster Intl

Sat 9/12

5:16 pm-12:26 pm

2 stops19h 10m

$367

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

3:55 pm-10:12 am

1 stop17h 17m

Montego Bay Sangster Intl

Thu 12/10

2:30 pm-9:19 am

1 stop19h 49m

$368

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

3:55 pm-10:13 am

2 stops17h 18m

Montego Bay Sangster Intl

Thu 12/10

3:12 pm-9:19 am

1 stop19h 07m

$372

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 12/5

5:00 am-4:12 pm

2 stops10h 12m

Montego Bay Sangster Intl

Sat 12/12

5:14 pm-9:53 am

2 stops17h 39m

$400

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 12/5

3:55 pm-10:12 am

1 stop17h 17m

Montego Bay Sangster Intl

Sat 12/12

2:30 pm-11:26 pm

1 stop9h 56m

$461
Quickest round-trip

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 9/5

5:00 am-1:12 pm

1 stop8h 12m

Montego Bay Sangster Intl

Sat 9/12

2:09 pm-8:50 pm

1 stop6h 41m

$466

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

3:55 pm-10:13 am

2 stops17h 18m

Montego Bay Sangster Intl

Thu 12/10

2:02 pm-11:49 pm

2 stops10h 47m

$471

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

6:45 am-4:12 pm

2 stops32h 27m

Montego Bay Sangster Intl

Thu 12/10

3:36 pm-12:12 am

2 stops33h 36m

$507

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Jamaica from

How to get the cheapest flight ticket from Madison to Jamaica

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 Jamaica?

The cheapest month to fly to Jamaica from Madison is in February. Flight prices, which tend to average around $213, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of February, then flying in June is also cheap. Prices for this month can be found on momondo for an average of $356.

Can stopping save me money on Madison to Jamaica flights?

You could potentially save up to 6% on your flight if you consider stops on a Madison to Jamaica flight.

Cheap Madison to Jamaica flight deals and tips

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

Fastest flight time

10h 12m

Direct flights

None
The fastest flight from Madison to Jamaica takes 10h 12m
There are no direct flights from Madison to Jamaica. There are no popular flight routes from Madison to Jamaica.
Search flight deals

Frequently asked questions about flying from Madison to Jamaica

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

    Prices for flights from Madison Truax Field Airport to Jamaica were last updated today.

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

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

    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 Jamaica.

  • What documentation or ID do you need to fly to Jamaica?

    The required travel and health documents for your Jamaica 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 Jamaica. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Madison to Jamaica

Compare and see reviews for airlines that fly from Madison to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $390Free CancellationRating
7.4
9,810 reviews
Search United Airlines flights
American AirlinesPriceFrom $484Free CancellationRating
7.1
11,644 reviews
Search American Airlines flights

Why use momondo?

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

It is quick and easy to find Madison to Jamaica flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Jamaica that suits you.

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

Yes. All flights to Jamaica from Madison on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Madison to Jamaica?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Madison to Jamaica.

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

Price alerts on flights to Jamaica from Madison are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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