$137+ Cheap flights from Milwaukee (MKE) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Caribbean 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 Milwaukee to Caribbean
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Cheapest flights from Milwaukee to CaribbeanExplore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:11 pm -
1 stop13h 48m
Mon 11/2310:21 pm -
1 stop21h 05m
Deal found 11/1![Frontier logo]()
$352
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:15 am -
1 stop11h 34m
Sun 11/227:17 am -
1 stop12h 09m
Deal found 11/2![Frontier logo]()
$398
This Frontier deal was found by Cheapflights users on 10/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:24 pm -
1 stop6h 47m
Mon 12/711:48 am -
1 stop7h 30m
Deal found 10/31![Frontier logo]()
$402
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:15 am -
1 stop14h 31m
Tue 11/243:55 am -
1 stop15h 31m
Deal found 11/4![Frontier logo]()
$406
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:11 pm -
1 stop13h 48m
Tue 11/243:55 am -
1 stop15h 31m
Deal found 10/31![Frontier logo]()
$424
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:05 am -
1 stop7h 05m
Tue 12/156:40 am -
1 stop7h 20m
Deal found 11/3![Southwest logo]()
$426
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Wed 12/212:38 pm -
1 stop9h 33m
Sun 12/66:38 pm -
1 stop7h 17m
Deal found 11/2![American Airlines logo]()
$431
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:10 am -
2 stops14h 40m
Wed 12/912:30 pm -
1 stop10h 35m
Deal found 11/4![Southwest logo]()
$436
This Frontier deal was found by Cheapflights users on 11/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:15 am -
1 stop11h 34m
Mon 11/237:17 am -
1 stop12h 09m
Deal found 11/4![Frontier logo]()
$438
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:09 am -
1 stop12h 03m
Sun 12/204:31 pm -
1 stop9h 28m
Deal found 11/4![American Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Wed 12/25:00 am -
2 stops14h 12m
Wed 12/97:00 am -
2 stops9h 21m
Deal found 11/2![American Airlines logo]()
$451
This Southwest deal was found by Cheapflights users on 10/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:10 am -
1 stop8h 35m
Wed 12/91:00 pm -
1 stop9h 25m
Deal found 10/31![Southwest logo]()
$453
Best flights from Milwaukee to CaribbeanDiscover carefully curated flight deals from Milwaukee to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Milwaukee to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Sat 1/309:20 am -
2 stops11h 02m
Mon 2/83:46 pm -
1 stop8h 59m
Deal found 11/1![United Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 11/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/73:22 pm -
1 stop6h 36m
Fri 2/126:30 pm -
1 stop7h 26m
Deal found 11/1![Delta logo]()
$426
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:15 am -
1 stop9h 00m
Tue 12/152:25 pm -
2 stops9h 55m
Deal found 11/3![Southwest logo]()
$426
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Mon 11/306:45 am -
1 stop6h 47m
Mon 12/76:09 pm -
2 stops18h 57m
Deal found 11/2![American Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/1212:40 pm -
1 stop7h 05m
Tue 2/95:35 am -
1 stop7h 15m
Deal found 11/4![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Sun 1/319:20 am -
2 stops11h 02m
Mon 2/88:05 am -
2 stops10h 41m
Deal found 11/3![United Airlines logo]()
$458
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:20 am -
2 stops9h 35m
Wed 12/910:45 am -
1 stop8h 35m
Deal found 11/4![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Sat 11/286:48 am -
1 stop6h 00m
Sat 12/56:00 pm -
1 stop17h 14m
Deal found 10/31![United Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 11/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/257:00 am -
1 stop6h 45m
Thu 4/291:25 pm -
1 stop8h 43m
Deal found 11/1![Delta logo]()
$521
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:55 am -
1 stop6h 30m
Fri 11/201:50 pm -
1 stop11h 00m
Deal found 11/1![Southwest logo]()
$453
This Delta deal was found by Cheapflights users on 11/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/45:30 am -
1 stop7h 23m
Sun 2/73:11 pm -
1 stop7h 19m
Deal found 11/2![Delta logo]()
$522
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Fri 1/89:20 am -
1 stop9h 40m
Sat 1/168:05 am -
2 stops10h 41m
Deal found 10/31![United Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:10 am -
1 stop8h 35m
Wed 12/91:00 pm -
1 stop9h 25m
Deal found 11/4![Southwest logo]()
$463
This Delta deal was found by Cheapflights users on 11/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/225:55 am -
1 stop7h 50m
Fri 4/301:25 pm -
1 stop8h 43m
Deal found 11/1![Delta logo]()
$522
This American Airlines deal was found by Cheapflights users on 10/31. 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.
Fri 1/153:00 pm -
2 stops18h 30m
Tue 1/191:44 pm -
2 stops20h 25m
Deal found 10/31![American Airlines logo]()
$663
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/147:00 pm -
2 stops20h 05m
Tue 4/202:35 pm -
1 stop9h 52m
Deal found 11/2![United Airlines logo]()
$518
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/163:50 pm -
1 stop7h 00m
Sat 12/197:15 pm -
1 stop7h 05m
Deal found 11/2![Southwest logo]()
$481
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/317:00 am -
1 stop6h 20m
Thu 2/41:30 pm -
2 stops11h 29m
Deal found 11/4![Delta logo]()
$538
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 2/132:23 pm -
2 stops20h 45m
Sat 2/209:15 am -
2 stops14h 49m
Deal found 11/2![American Airlines logo]()
$672
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Sat 1/165:00 am -
2 stops10h 50m
Fri 1/223:00 pm -
1 stop9h 31m
Deal found 11/1![United Airlines logo]()
$522
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/195:15 am -
1 stop7h 40m
Mon 1/252:10 pm -
2 stops10h 00m
Deal found 11/4![Southwest logo]()
$484
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:30 am -
1 stop7h 35m
Mon 12/284:20 pm -
1 stop9h 39m
Deal found 11/3![Delta logo]()
$542
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/16:41 pm -
1 stop17h 40m
Sat 5/812:15 pm -
1 stop11h 32m
Deal found 11/4![American Airlines logo]()
$693
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:55 pm -
1 stop11h 55m
Mon 12/2110:30 pm -
1 stop12h 45m
Deal found 11/4![Southwest logo]()
$492
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:30 am -
1 stop8h 54m
Mon 12/284:20 pm -
1 stop9h 39m
Deal found 11/3![Delta logo]()
$545
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/155:00 am -
2 stops10h 05m
Tue 4/202:35 pm -
1 stop9h 52m
Deal found 11/2![United Airlines logo]()
$554
This American Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 3/2312:09 pm -
1 stop25h 25m
Thu 4/14:41 pm -
2 stops20h 24m
Deal found 10/31![American Airlines logo]()
$700
This Delta deal was found by Cheapflights users on 11/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/255:55 am -
1 stop7h 30m
Sat 5/12:15 pm -
1 stop10h 34m
Deal found 11/2![Delta logo]()
$559
This Southwest deal was found by Cheapflights users on 10/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:10 am -
1 stop6h 25m
Tue 12/151:30 pm -
1 stop8h 35m
Deal found 10/31![Southwest logo]()
$510
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Thu 2/185:00 am -
2 stops10h 35m
Mon 2/225:45 pm -
2 stops15h 51m
Deal found 11/1![United Airlines logo]()
$576
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated November 4, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:15 am -
1 stop11h 34m
Sun 11/227:17 am -
1 stop12h 09m
Deal found 11/2![Frontier logo]()
$398
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:15 am -
1 stop14h 31m
Tue 11/243:55 am -
1 stop15h 31m
Deal found 11/4![Frontier logo]()
$406
This Frontier deal was found by Cheapflights users on 11/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:15 am -
1 stop11h 34m
Mon 11/237:17 am -
1 stop12h 09m
Deal found 11/4![Frontier logo]()
$438
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:11 pm -
1 stop13h 48m
Mon 11/2310:21 pm -
1 stop21h 05m
Deal found 11/1![Frontier logo]()
$352
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:11 pm -
1 stop13h 48m
Tue 11/243:55 am -
1 stop15h 31m
Deal found 10/31![Frontier logo]()
$424
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Wed 12/212:38 pm -
1 stop9h 33m
Sun 12/66:38 pm -
1 stop7h 17m
Deal found 11/2![American Airlines logo]()
$431
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:15 pm -
2 stops8h 35m
Wed 12/92:25 pm -
2 stops9h 55m
Deal found 11/4![Southwest logo]()
$436
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Wed 12/25:00 am -
2 stops14h 12m
Wed 12/97:00 am -
2 stops9h 21m
Deal found 11/2![American Airlines logo]()
$451
This Frontier deal was found by Cheapflights users on 10/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:24 pm -
1 stop6h 47m
Mon 12/711:48 am -
1 stop7h 30m
Deal found 10/31![Frontier logo]()
$402
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:05 am -
1 stop7h 05m
Tue 12/156:40 am -
1 stop7h 20m
Deal found 11/3![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 10/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:10 am -
1 stop8h 35m
Wed 12/91:00 pm -
1 stop9h 25m
Deal found 10/31![Southwest logo]()
$453
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:40 pm -
1 stop9h 31m
Sun 12/202:50 pm -
1 stop11h 09m
Deal found 11/4![American Airlines logo]()
$446
One-way flights from Milwaukee to CaribbeanSearch for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:13 pm -
2 stops28h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/238:15 am -
2 stops15h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:11 pm -
1 stop13h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 11/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/148:15 am -
2 stops15h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$199
This Delta deal was found by Cheapflights users on 10/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:00 am -
1 stop6h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Delta logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:11 pm -
2 stops18h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$203
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 1/95:50 pm -
2 stops19h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$208
This Trip.com deal was found by Cheapflights users on 10/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:11 pm -
1 stop13h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$211
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:10 pm -
1 stop17h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![United Airlines logo]()
$212
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Sat 1/303:34 pm -
2 stops19h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$212
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 1/2312:35 pm -
1 stop9h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$213
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:15 pm -
1 stop11h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$218
Find flight deals from Milwaukee to Caribbean
Keep the following information in mind while searching for Milwaukee to Caribbean flight deals. Data was last updated November 4, 2026.
Round-trip from | $331 (Cheapflightsfares) |
|---|---|
One-way from | $137 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $481 |
Good round-trip deal | $834 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee to Caribbean 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 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/9
5:30 am-4:44 pm
1 stop10h 14m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$202
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 11/15
7:00 am-2:03 pm
1 stop6h 03m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$202
MilwaukeeProvidenciales
MKE Milwaukee-Mitchell - PLS Providenciales
MKEPLS
Milwaukee-Mitchell
Sun 12/13
7:10 pm-1:17 pm
1 stop17h 07m
Providenciales
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$212
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/30
6:24 am-1:50 pm
1 stop6h 26m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$212
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Wed 11/25
2:45 pm-12:20 am
1 stop7h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$213
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 11/23
6:47 am-10:22 pm
2 stops13h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$213
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Fri 11/27
7:55 pm-10:10 am
1 stop12h 15m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$213
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sun 12/13
12:35 pm-1:10 am
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$213
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sun 1/10
11:30 am-9:55 pm
1 stop8h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$218
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 12/3
2:15 pm-12:50 am
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$238
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Milwaukee with our price prediction graph.
MKE-SJU
MKE-MBJ
MKE-PLS
MKE-NAS
MKE-STT
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 Milwaukee to Caribbean
MKE-0CB
MKE-SJU
MKE-MBJ
MKE-PLS
MKE-NAS
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $497). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $733). 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.
How far ahead should I book a flight from Milwaukee to Caribbean?
The best time to book flights from Milwaukee to Caribbean is 76 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated November 4, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Milwaukee to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Caribbean by cabin class
Find flights from Milwaukee to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Caribbean flights
Browse other Milwaukee and Caribbean flight options. Last updated on November 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Milwaukee to Caribbean flights
Consider these flights traveling from Milwaukee to Caribbean.
Top 7 airlines flying from Milwaukee to Caribbean
Discover the top 7 airlines that operate flights from Milwaukee to Caribbean. 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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$595 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$672 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$655 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$273 | Average$548 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$323 | Average$709 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$488 | Average$868 | FlexibilityNo cancel fee | On-time83% |