$119+ Cheap flights from Milwaukee (MKE) to Caribbean
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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Sep 21 — Sep 281
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
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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 August 22, 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 August 22, 2026.
This American Airlines deal was found by Cheapflights users on 8/22. 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 10/176:27 pm -
2 stops17h 31m
Thu 10/223:46 pm -
2 stops20h 45m
Deal found 8/22![American Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Thu 10/1510:15 am -
1 stop11h 50m
Thu 10/227:00 am -
1 stop13h 15m
Deal found 8/20![Frontier logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Tue 9/155:00 am -
1 stop8h 44m
Tue 9/151:00 am -
2 stops11h 30m
Deal found 8/20![United Airlines logo]()
$323
This Frontier deal was found by Cheapflights users on 8/17. 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.
Sun 8/3012:10 pm -
1 stop13h 05m
Wed 9/92:57 am -
1 stop7h 11m
Deal found 8/17![Frontier logo]()
$328
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 12/47:20 pm -
1 stop12h 40m
Thu 12/102:25 pm -
1 stop8h 55m
Deal found 8/21![Southwest logo]()
$331
This Frontier deal was found by Cheapflights users on 8/21. 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.
Tue 9/812:10 pm -
1 stop13h 05m
Sat 9/192:57 am -
1 stop7h 25m
Deal found 8/21![Frontier logo]()
$332
This Frontier deal was found by Cheapflights users on 8/22. 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 9/1010:10 am -
1 stop12h 03m
Sat 9/122:57 am -
1 stop7h 25m
Deal found 8/22![Frontier logo]()
$333
This Frontier deal was found by Cheapflights users on 8/21. 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.
Sun 8/3012:10 pm -
1 stop13h 05m
Sat 9/129:50 pm -
1 stop12h 32m
Deal found 8/21![Frontier logo]()
$335
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/317:19 pm -
2 stops19h 33m
Sat 11/76:28 am -
1 stop7h 20m
Deal found 8/19![American Airlines logo]()
$342
This Frontier deal was found by Cheapflights users on 8/20. 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 9/312:10 pm -
1 stop13h 05m
Sat 9/129:50 pm -
1 stop12h 32m
Deal found 8/20![Frontier logo]()
$343
This Faresmojo deal was found by Cheapflights users on 8/19. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:30 am -
1 stop9h 30m
Sun 9/209:25 pm -
1 stop12h 25m
Deal found 8/19![JetBlue logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/19. 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 12/25:10 am -
2 stops10h 55m
Thu 12/103:49 pm -
1 stop17h 59m
Deal found 8/19![American Airlines logo]()
$347
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 August 22, 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 August 22, 2026.
This Southwest deal was found by Cheapflights users on 8/20. 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 9/241:55 pm -
1 stop9h 00m
Mon 9/285:30 am -
1 stop7h 25m
Deal found 8/20![Southwest logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/22. 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 9/1610:30 am -
2 stops12h 20m
Fri 9/181:00 am -
1 stop10h 29m
Deal found 8/22![United Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 8/18. 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 1/267:00 am -
1 stop7h 25m
Tue 2/92:20 pm -
1 stop7h 48m
Deal found 8/18![Delta logo]()
$413
This American Airlines deal was found by Cheapflights users on 8/22. 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 10/38:14 pm -
2 stops16h 39m
Tue 10/135:13 pm -
2 stops19h 01m
Deal found 8/22![American Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 8/22. 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 9/306:05 am -
1 stop9h 20m
Tue 10/612:40 pm -
1 stop11h 15m
Deal found 8/22![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 8/18. 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 9/2111:00 am -
1 stop11h 10m
Sun 9/279:25 pm -
1 stop12h 30m
Deal found 8/18![Southwest logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/510:19 am -
2 stops12h 31m
Fri 9/111:00 am -
1 stop10h 29m
Deal found 8/20![United Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 8/19. 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 1/263:49 pm -
2 stops20h 09m
Tue 2/912:43 pm -
2 stops10h 59m
Deal found 8/19![American Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 8/18. 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.
Fri 12/1112:42 pm -
1 stop8h 38m
Wed 12/166:35 pm -
1 stop7h 19m
Deal found 8/18![Delta logo]()
$426
This Southwest deal was found by Cheapflights users on 8/20. 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 9/241:55 pm -
1 stop7h 20m
Tue 9/2911:50 am -
1 stop10h 30m
Deal found 8/20![Southwest logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/21. 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 1/106:00 am -
1 stop6h 46m
Sat 1/165:26 pm -
2 stops19h 08m
Deal found 8/21![United Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 8/19. 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 12/55:10 am -
2 stops13h 48m
Sat 12/123:30 pm -
1 stop21h 00m
Deal found 8/19![American Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 8/19. 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.
Fri 11/2712:45 pm -
1 stop10h 20m
Sat 12/55:40 am -
2 stops10h 40m
Deal found 8/19![Southwest logo]()
$395
This American Airlines deal was found by Cheapflights users on 8/20. 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 10/246:27 pm -
1 stop16h 33m
Wed 10/281:00 pm -
1 stop7h 52m
Deal found 8/20![American Airlines logo]()
$435
This United Airlines deal was found by Cheapflights users on 8/21. 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 1/16:40 am -
2 stops9h 10m
Thu 1/73:05 pm -
1 stop9h 34m
Deal found 8/21![United Airlines logo]()
$461
This Delta deal was found by Cheapflights users on 8/17. 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.
Wed 2/35:55 am -
1 stop5h 45m
Sun 2/72:05 pm -
1 stop8h 03m
Deal found 8/17![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 8/19. 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.
Fri 9/111:55 pm -
1 stop7h 20m
Tue 9/1511:50 am -
2 stops10h 10m
Deal found 8/19![Southwest logo]()
$396
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Sun 1/175:56 pm -
2 stops17h 22m
Fri 1/221:18 pm -
2 stops11h 04m
Deal found 8/20![American Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 8/21. 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.
Wed 2/176:00 am -
1 stop8h 15m
Tue 2/236:10 pm -
1 stop6h 39m
Deal found 8/21![Delta logo]()
$538
This United Airlines deal was found by Cheapflights users on 8/22. 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 10/245:00 am -
2 stops10h 05m
Wed 10/282:25 pm -
2 stops22h 03m
Deal found 8/22![United Airlines logo]()
$498
This Southwest deal was found by Cheapflights users on 8/19. 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 9/101:55 pm -
1 stop9h 00m
Mon 9/145:30 am -
1 stop7h 25m
Deal found 8/19![Southwest logo]()
$412
This American Airlines deal was found by Cheapflights users on 8/17. 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 10/305:10 pm -
2 stops15h 17m
Wed 11/42:26 pm -
1 stop6h 49m
Deal found 8/17![American Airlines logo]()
$482
This Delta deal was found by Cheapflights users on 8/20. 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.
Fri 1/17:00 am -
1 stop6h 25m
Sat 1/912:40 pm -
1 stop9h 53m
Deal found 8/20![Delta logo]()
$543
This United Airlines deal was found by Cheapflights users on 8/20. 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 10/246:43 pm -
2 stops20h 47m
Sat 10/311:55 pm -
1 stop8h 20m
Deal found 8/20![United Airlines logo]()
$511
This United Airlines deal was found by Cheapflights users on 8/20. 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 11/286:47 am -
1 stop5h 58m
Sat 12/52:50 pm -
1 stop8h 49m
Deal found 8/20![United Airlines logo]()
$511
This Delta deal was found by Cheapflights users on 8/18. 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 9/155:30 am -
1 stop6h 57m
Wed 9/302:53 pm -
1 stop9h 55m
Deal found 8/18![Delta logo]()
$600
This American Airlines deal was found by Cheapflights users on 8/19. 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 12/17:24 pm -
2 stops18h 14m
Tue 12/83:15 pm -
2 stops18h 33m
Deal found 8/19![American Airlines logo]()
$550
This United Airlines deal was found by Cheapflights users on 8/18. 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 2/105:00 am -
1 stop7h 45m
Wed 2/172:55 pm -
1 stop6h 59m
Deal found 8/18![United Airlines logo]()
$511
This Southwest deal was found by Cheapflights users on 8/22. 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 10/195:00 am -
1 stop8h 00m
Mon 10/262:50 pm -
1 stop10h 45m
Deal found 8/22![Southwest logo]()
$525
This Delta deal was found by Cheapflights users on 8/20. 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 11/95:30 am -
1 stop7h 50m
Thu 11/124:35 pm -
1 stop9h 19m
Deal found 8/20![Delta logo]()
$617
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated August 22, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/17. 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.
Sun 8/3012:10 pm -
1 stop13h 05m
Wed 9/92:57 am -
1 stop7h 11m
Deal found 8/17![Frontier logo]()
$328
This Frontier deal was found by Cheapflights users on 8/21. 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.
Sun 8/3012:10 pm -
1 stop13h 05m
Sat 9/129:50 pm -
1 stop12h 32m
Deal found 8/21![Frontier logo]()
$335
This Frontier deal was found by Cheapflights users on 8/20. 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 9/312:10 pm -
1 stop13h 05m
Sat 9/129:50 pm -
1 stop12h 32m
Deal found 8/20![Frontier logo]()
$343
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:10 pm -
1 stop27h 39m
Wed 9/92:57 am -
1 stop7h 11m
Deal found 8/18![Frontier logo]()
$357
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:10 pm -
1 stop27h 39m
Wed 9/910:42 am -
1 stop23h 26m
Deal found 8/18![Frontier logo]()
$365
This Frontier deal was found by Cheapflights users on 8/21. 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.
Tue 9/812:10 pm -
1 stop13h 05m
Sat 9/192:57 am -
1 stop7h 25m
Deal found 8/21![Frontier logo]()
$332
This Frontier deal was found by Cheapflights users on 8/22. 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 9/1010:10 am -
1 stop12h 03m
Sat 9/122:57 am -
1 stop7h 25m
Deal found 8/22![Frontier logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Tue 9/155:00 am -
1 stop8h 44m
Tue 9/151:00 am -
1 stop10h 33m
Deal found 8/20![United Airlines logo]()
$323
This CheapOair deal was found by Cheapflights users on 8/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:55 am -
2 stops21h 09m
Sat 9/196:42 pm -
1 stop15h 40m
Deal found 8/19![Multiple Airlines logo]()
$351
This Faresmojo deal was found by Cheapflights users on 8/19. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:30 am -
1 stop9h 30m
Sun 9/209:25 pm -
1 stop12h 25m
Deal found 8/19![JetBlue logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/22. 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 9/245:53 pm -
2 stops16h 07m
Tue 9/293:41 pm -
2 stops17h 20m
Deal found 8/22![American Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/255:53 pm -
2 stops21h 20m
Sat 10/34:53 pm -
2 stops20h 55m
Deal found 8/21![American Airlines logo]()
$421
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 August 22, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
This United Airlines deal was found by Cheapflights users on 8/22. 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 10/1710:42 am -
2 stops12h 08m
Deal found 8/22![United Airlines logo]()
$119
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Sun 9/137:00 am -
1 stop7h 07m
Deal found 8/19![American Airlines logo]()
$121
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/122:48 pm -
2 stops17h 36m
Deal found 8/20![American Airlines logo]()
$122
This Priceline deal was found by Cheapflights users on 8/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:10 pm -
1 stop13h 05m
Deal found 8/18![Frontier logo]()
$124
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/218:14 pm -
2 stops17h 36m
Deal found 8/19![American Airlines logo]()
$125
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/95:53 pm -
2 stops16h 07m
Deal found 8/19![American Airlines logo]()
$126
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/166:01 am -
2 stops13h 46m
Deal found 8/20![American Airlines logo]()
$127
This Faresmojo deal was found by Cheapflights users on 8/19. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:05 pm -
1 stop7h 00m
Deal found 8/19![JetBlue logo]()
$129
This Priceline deal was found by Cheapflights users on 8/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1310:10 am -
1 stop22h 25m
Deal found 8/18![Frontier logo]()
$130
This Frontier deal was found by Cheapflights users on 8/20. 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 9/1010:10 am -
1 stop12h 03m
Deal found 8/20![Frontier logo]()
$134
This American Airlines deal was found by Cheapflights users on 8/20. 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 2/67:19 pm -
1 stop17h 21m
Deal found 8/20![American Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/166:27 pm -
2 stops17h 31m
Deal found 8/19![American Airlines logo]()
$155
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 August 22, 2026.
Round-trip from | $302 (American Airlines) |
|---|---|
One-way from | $119 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $418 |
Good round-trip deal | $729 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 August 22, 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
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 9/24
1:55 pm-11:55 pm
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Mon 9/28
5:30 am-11:55 am
1 stop7h 25m
$366
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Wed 9/30
6:05 am-4:25 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Tue 10/6
12:40 pm-10:55 pm
1 stop11h 15m
$366
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 9/21
11:00 am-11:10 pm
1 stop11h 10m
San Juan Luis Munoz Marin Intl
Sun 9/27
9:25 pm-8:55 am
1 stop12h 30m
$366
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 9/24
1:55 pm-10:15 pm
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Tue 9/29
11:50 am-9:20 pm
1 stop10h 30m
$366
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Wed 9/16
10:30 am-11:50 pm
2 stops12h 20m
San Juan Luis Munoz Marin Intl
Fri 9/18
1:00 am-10:29 am
1 stop10h 29m
$368
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Fri 11/27
12:45 pm-1:05 am
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Sat 12/5
5:40 am-2:20 pm
2 stops10h 40m
$395
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Fri 9/11
1:55 pm-10:15 pm
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Tue 9/15
11:50 am-9:00 pm
2 stops10h 10m
$396
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 9/5
10:19 am-11:50 pm
2 stops12h 31m
San Juan Luis Munoz Marin Intl
Fri 9/11
1:00 am-10:29 am
1 stop10h 29m
$407
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 9/10
1:55 pm-11:55 pm
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Mon 9/14
5:30 am-11:55 am
1 stop7h 25m
$412
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Tue 1/26
7:00 am-3:25 pm
1 stop7h 25m
Montego Bay Sangster Intl
Tue 2/9
2:20 pm-9:08 pm
1 stop7h 48m
$413
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-STT
MKE-MBJ
MKE-GCM
MKE-PLS
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-STT
MKE-MBJ
MKE-GCM
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, May is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $491). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $737). 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 42 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 August 22, 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
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 August 22, 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 August 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$215 | Average$597 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$572 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$674 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$319 | Average$720 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$465 | Average$567 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$547 | Average$853 | FlexibilityNo cancel fee | On-time83% |