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$167 Find cheap flights from Caribbean Islands to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Madison departing on 8/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Fri 6/7
Fri 6/14

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In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

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Good to know

Low season

March

High season

May

Cheapest flight

$167
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from San Juan to Madison

FAQs for booking flights from Caribbean Islands to Madison

  • How does KAYAK find such low prices on flights from Caribbean Islands to Madison?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean Islands to Madison.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Madison?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean Islands to Madison?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Madison with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Madison?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Madison from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Caribbean Islands to Madison?

Find which airlines fly direct from Caribbean Islands to Truax Field, which days they fly and book direct flights.

Nonstop departures

Caribbean Islands to Madison Truax Field

Monday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Tuesday

ANA, Aeromexico, Air Canada, +19 more

ANA, Aeromexico, +20 more

Wednesday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Thursday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Friday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Saturday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Sunday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

See more direct flights

Nonstop returns

Madison Truax Field to Caribbean Islands

Monday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Tuesday

ANA, Aeromexico, Air Canada, +19 more

ANA, Aeromexico, +20 more

Wednesday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Thursday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Friday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Saturday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Sunday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

See more direct flights
See more direct flights

Top airline flying from Caribbean Islands to Madison

 
Need help choosing which airline to fly with from Caribbean Islands to Madison? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
American AirlinesOverall score based on 14678 reviews
7.2Comfort
7.1Entertainment
7.6Boarding
8.0Crew
6.6Food
Airline reviews

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

10.0 ExcellentLuis, May 2024PHX - MIA
Read more about American Airlines reviews

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Horrible - they lied to me about baggage & boarding, even though I specifically spoke to their agents the day before my flight about my issue. When I showed up they did not let me board and stranded me at my airport until I bought a new flight with money I did not have to spend.

All four American Airlines flights I took in last seven days were delayed. Caused me loads of problems, missed meetings, loss of time and money.

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

Book cheap flights from Caribbean Islands to Madison

Recent round-trip flight deals

8/27Tue
2 stopsAmerican Airlines
9h 42mSJU-MSN
9/7Sat
2 stopsAmerican Airlines
17h 42mMSN-SJU
$333
8/27Tue
2 stopsAmerican Airlines
11h 14mSJU-MSN
9/7Sat
1 stopAmerican Airlines
9h 51mMSN-SJU
$334
8/27Tue
1 stopAmerican Airlines
8h 36mSJU-MSN
9/7Sat
1 stopAmerican Airlines
9h 51mMSN-SJU
$395
9/20Fri
1 stopDelta
9h 06mNAS-MSN
9/24Tue
1 stopDelta
5h 12mMSN-NAS
$443
9/20Fri
1 stopDelta
9h 06mNAS-MSN
9/24Tue
2 stopsDelta
17h 07mMSN-NAS
$448
9/20Fri
1 stopDelta
9h 06mNAS-MSN
9/24Tue
1 stopDelta
6h 23mMSN-NAS
$453
9/20Fri
1 stopDelta
9h 06mNAS-MSN
9/24Tue
2 stopsDelta
17h 07mMSN-NAS
$458
6/7Fri
1 stopUnited Airlines
8h 31mMBJ-MSN
6/14Fri
2 stopsUnited Airlines
33h 06mMSN-MBJ
$464
6/7Fri
2 stopsUnited Airlines
23h 03mMBJ-MSN
6/14Fri
2 stopsUnited Airlines
33h 06mMSN-MBJ
$514
5/27Mon
3 stops
27h 47mMBJ-MSN
9/9Mon
2 stops
18h 06mMSN-MBJ
$1,533

Search by stops

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Recent one-way flight deals

8/29Thu
2 stopsAmerican Airlines
10h 55mSJU-MSN
$167
5/21Tue
1 stop
8h 31mSJU-MSN
$190
6/3Mon
2 stopsAmerican Airlines
21h 10mSJU-MSN
$225
8/29Thu
1 stopAmerican Airlines
15h 19mSJU-MSN
$228
6/12Wed
2 stopsDelta
18h 16mMBJ-MSN
$258
8/30Fri
1 stopDelta
10h 48mSJU-MSN
$267
6/12Wed
1 stopDelta
23h 24mMBJ-MSN
$272
5/21Tue
2 stopsUnited Airlines
11h 25mSJU-MSN
$277
6/9Sun
1 stopUnited Airlines
7h 36mMBJ-MSN
$288
5/18Sat
2 stopsAir Canada
27h 30mMBJ-MSN
$980

Search by stops

Search by airline

Search by price

Last minute flights from Caribbean Islands to Madison

Last minute flight, train and bus deals

5/13Mon
multi-stopAmerican Airlines
16h 55mSJU-MSN
5/18Sat
multi-stopAmerican Airlines
14h 06mMSN-SJU
$693
5/13Mon
multi-stopAmerican Airlines
11h 00mSJU-MSN
5/18Sat
multi-stopAmerican Airlines
21h 10mMSN-SJU
$694
5/13Mon
multi-stopUnited Airlines
10h 14mSJU-MSN
5/18Sat
multi-stopUnited Airlines
10h 55mMSN-SJU
$749
5/13Mon
multi-stopAmerican Airlines
16h 55mSJU-MSN
5/18Sat
multi-stopAmerican Airlines
14h 06mMSN-SJU
$753
5/10Fri
multi-stopUnited Airlines
24h 45mNAS-MSN
5/14Tue
multi-stopUnited Airlines
6h 31mMSN-NAS
$802
5/13Mon
multi-stopUnited Airlines
11h 25mSJU-MSN
5/18Sat
multi-stopUnited Airlines
10h 55mMSN-SJU
$897
5/10Fri
multi-stopUnited Airlines
9h 35mNAS-MSN
5/14Tue
multi-stopUnited Airlines
6h 31mMSN-NAS
$930

Search by stops

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Flights to Madison

Destination:

Madison (MSN)United States

Return flight deals:

Madison - Caribbean Islands

Cabin classes:

$528
$456
$418
$88

Browse destinations: