$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 27 — Oct 41
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 28, 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 28, 2026.
This American Airlines deal was found by Cheapflights users on 8/26. 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 10/276:02 pm -
2 stops19h 53m
Sat 10/313:58 pm -
2 stops21h 10m
Deal found 8/26![American Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 8/27. 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 9/195:00 am -
2 stops14h 38m
Tue 9/224:20 pm -
1 stop8h 17m
Deal found 8/27![United Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 8/27. 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 11/17:05 am -
1 stop15h 11m
Sat 11/77:30 am -
2 stops17h 36m
Deal found 8/27![American Airlines logo]()
$308
This Travelocity deal was found by Cheapflights users on 8/28. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:10 am -
1 stop14h 42m
Sat 10/32:57 am -
1 stop7h 25m
Deal found 8/28![Frontier logo]()
$312
This American Airlines deal was found by Cheapflights users on 8/26. 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 9/165:53 pm -
2 stops14h 31m
Fri 9/256:00 am -
2 stops14h 33m
Deal found 8/26![American Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 8/27. 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 11/212:45 pm -
2 stops10h 10m
Sat 11/76:45 am -
1 stop7h 20m
Deal found 8/27![Southwest logo]()
$318
This United Airlines deal was found by Cheapflights users on 8/24. 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 -
2 stops14h 38m
Tue 9/151:00 am -
2 stops11h 30m
Deal found 8/24![United Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/1710:10 am -
1 stop14h 42m
Tue 9/222:45 pm -
2 stops43h 23m
Deal found 8/24![Frontier logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/25. 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 10/319:23 am -
1 stop9h 37m
Sat 11/78:25 am -
1 stop8h 33m
Deal found 8/25![United Airlines logo]()
$328
This FlightHub deal was found by Cheapflights users on 8/27. 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.
Tue 11/310:15 am -
1 stop22h 00m
Sat 11/77:23 am -
1 stop27h 53m
Deal found 8/27![Frontier logo]()
$330
This Southwest deal was found by Cheapflights users on 8/26. 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 9/197:30 am -
2 stops9h 50m
Tue 9/225:15 am -
1 stop6h 40m
Deal found 8/26![Southwest logo]()
$331
This Priceline deal was found by Cheapflights users on 8/27. 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.
Thu 11/510:15 am -
1 stop14h 35m
Mon 11/163:55 am -
1 stop7h 21m
Deal found 8/27![Frontier logo]()
$332
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 28, 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 28, 2026.
This United Airlines deal was found by Cheapflights users on 8/27. 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 9/195:00 am -
2 stops14h 38m
Tue 9/224:20 pm -
1 stop8h 17m
Deal found 8/27![United Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 8/27. 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 10/92:25 pm -
1 stop6h 30m
Mon 10/128:50 pm -
1 stop13h 05m
Deal found 8/27![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 8/24. 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 1/265:55 am -
1 stop8h 30m
Tue 2/94:50 pm -
1 stop7h 59m
Deal found 8/24![Delta logo]()
$413
This American Airlines deal was found by Cheapflights users on 8/27. 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 2/76:13 am -
1 stop6h 53m
Sat 2/136:36 pm -
2 stops18h 36m
Deal found 8/27![American Airlines logo]()
$415
This United Airlines deal was found by Cheapflights users on 8/25. 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 -
2 stops14h 38m
Wed 9/167:00 am -
1 stop11h 09m
Deal found 8/25![United Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 8/25. 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 10/128:05 pm -
1 stop12h 05m
Sat 10/173:05 pm -
1 stop7h 20m
Deal found 8/25![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 8/25. 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 10/3110:48 am -
2 stops11h 48m
Sat 11/78:25 am -
1 stop7h 07m
Deal found 8/25![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 8/24. 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 8/24![Southwest logo]()
$366
This American Airlines deal was found by Cheapflights users on 8/27. 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 2/92:19 pm -
2 stops18h 48m
Deal found 8/27![American Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 8/27. 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 1/2110:25 am -
1 stop11h 25m
Thu 1/283:20 pm -
1 stop8h 17m
Deal found 8/27![Delta logo]()
$428
This United Airlines deal was found by Cheapflights users on 8/25. 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 1/912:14 pm -
1 stop6h 46m
Fri 1/152:05 am -
1 stop9h 41m
Deal found 8/25![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 8/23. 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 12/57:40 am -
1 stop6h 01m
Sat 12/123:30 pm -
1 stop21h 00m
Deal found 8/23![American Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 8/24. 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 1/105:55 am -
1 stop5h 55m
Fri 1/222:15 pm -
1 stop10h 34m
Deal found 8/24![Delta logo]()
$463
This American Airlines deal was found by Cheapflights users on 8/23. 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 2/226:38 pm -
1 stop14h 36m
Sat 2/273:25 pm -
1 stop17h 42m
Deal found 8/23![American Airlines logo]()
$435
This United Airlines deal was found by Cheapflights users on 8/25. 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 12/66:18 pm -
2 stops16h 55m
Wed 12/92:54 pm -
1 stop7h 06m
Deal found 8/25![United Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Mon 10/266:48 am -
1 stop6h 00m
Fri 10/302:01 pm -
1 stop8h 14m
Deal found 8/23![United Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 8/27. 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 2/35:35 am -
1 stop6h 20m
Sun 2/71:50 pm -
1 stop11h 05m
Deal found 8/27![Southwest logo]()
$505
This Delta deal was found by Cheapflights users on 8/23. 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 1/215:55 am -
1 stop5h 45m
Wed 1/272:05 pm -
1 stop10h 44m
Deal found 8/23![Delta logo]()
$511
This American Airlines deal was found by Cheapflights users on 8/27. 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 1/285:00 am -
2 stops11h 54m
Tue 2/22:22 pm -
2 stops9h 20m
Deal found 8/27![American Airlines logo]()
$482
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Mon 2/15:00 am -
1 stop7h 46m
Sat 2/63:20 pm -
1 stop8h 26m
Deal found 8/25![United Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 8/26. 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 12/305:00 am -
1 stop6h 35m
Wed 1/61:50 pm -
1 stop8h 00m
Deal found 8/26![Southwest logo]()
$507
This Delta deal was found by Cheapflights users on 8/26. 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.
Sat 1/305:55 am -
1 stop7h 30m
Sat 2/612:40 pm -
1 stop9h 53m
Deal found 8/26![Delta logo]()
$523
This American Airlines deal was found by Cheapflights users on 8/27. 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 2/43:49 pm -
2 stops20h 13m
Sun 2/73:20 pm -
1 stop9h 22m
Deal found 8/27![American Airlines logo]()
$487
This United Airlines deal was found by Cheapflights users on 8/23. 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 8/23![United Airlines logo]()
$418
This Southwest deal was found by Cheapflights users on 8/27. 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 11/285:00 am -
1 stop7h 25m
Sat 12/51:55 pm -
1 stop6h 30m
Deal found 8/27![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 8/25. 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 8/25![Delta logo]()
$538
This United Airlines deal was found by Cheapflights users on 8/27. 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 10/236:00 pm -
1 stop19h 30m
Tue 10/272:20 pm -
1 stop8h 44m
Deal found 8/27![United Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 8/23. 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 9/226:05 am -
1 stop5h 10m
Tue 9/291:10 pm -
1 stop9h 10m
Deal found 8/23![Southwest logo]()
$518
This American Airlines deal was found by Cheapflights users on 8/26. 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 2/27:19 pm -
2 stops19h 31m
Tue 2/93:00 pm -
1 stop10h 12m
Deal found 8/26![American Airlines logo]()
$544
This Delta deal was found by Cheapflights users on 8/23. 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 10/15:30 am -
1 stop7h 23m
Thu 10/83:19 pm -
1 stop9h 34m
Deal found 8/23![Delta logo]()
$547
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated August 28, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/24. 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 8/24![Frontier logo]()
$332
This Priceline deal was found by Cheapflights users on 8/24. 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
Wed 9/162:57 am -
1 stop7h 11m
Deal found 8/24![Frontier logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/24. 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 -
2 stops14h 38m
Tue 9/151:00 am -
2 stops11h 30m
Deal found 8/24![United Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 8/26. 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 9/165:53 pm -
2 stops14h 31m
Fri 9/256:00 am -
2 stops14h 33m
Deal found 8/26![American Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/1710:10 am -
1 stop14h 42m
Tue 9/222:45 pm -
2 stops43h 23m
Deal found 8/24![Frontier logo]()
$326
This Southwest deal was found by Cheapflights users on 8/28. 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 9/181:55 pm -
1 stop9h 00m
Tue 9/221:45 pm -
1 stop8h 25m
Deal found 8/28![Southwest logo]()
$340
This United Airlines deal was found by Cheapflights users on 8/27. 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 9/195:00 am -
2 stops14h 38m
Tue 9/224:20 pm -
1 stop8h 17m
Deal found 8/27![United Airlines logo]()
$306
This United Airlines deal was found by Cheapflights users on 8/27. 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 9/195:00 am -
2 stops14h 38m
Wed 9/234:20 pm -
1 stop8h 17m
Deal found 8/27![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 8/26. 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 9/197:30 am -
2 stops9h 50m
Tue 9/225:15 am -
1 stop6h 40m
Deal found 8/26![Southwest logo]()
$331
This American Airlines deal was found by Cheapflights users on 8/26. 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 9/258:14 pm -
2 stops16h 43m
Mon 10/510:36 am -
2 stops14h 21m
Deal found 8/26![American Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 8/25. 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 9/265:53 pm -
2 stops17h 58m
Sun 10/41:41 pm -
2 stops21h 33m
Deal found 8/25![American Airlines logo]()
$415
This Travelocity deal was found by Cheapflights users on 8/28. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:10 am -
1 stop14h 42m
Sat 10/32:57 am -
1 stop7h 25m
Deal found 8/28![Frontier logo]()
$312
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 28, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This United Airlines deal was found by Cheapflights users on 8/26. 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 8/26![United Airlines logo]()
$119
This American Airlines deal was found by Cheapflights users on 8/26. 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 stops16h 07m
Deal found 8/26![American Airlines logo]()
$122
This American Airlines deal was found by Cheapflights users on 8/26. 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 10/213:09 pm -
2 stops17h 37m
Deal found 8/26![American Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 8/23. 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 8/23![American Airlines logo]()
$125
This Priceline deal was found by Cheapflights users on 8/24. 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.
Thu 10/810:15 am -
1 stop14h 38m
Deal found 8/24![Frontier logo]()
$134
This American Airlines deal was found by Cheapflights users on 8/24. 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 1/56:49 pm -
2 stops17h 13m
Deal found 8/24![American Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 8/27. 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 11/77:05 am -
1 stop15h 11m
Deal found 8/27![American Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 8/27. 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 9/285:53 pm -
2 stops17h 58m
Deal found 8/27![American Airlines logo]()
$155
This Southwest deal was found by Cheapflights users on 8/26. 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 9/251:55 pm -
1 stop9h 00m
Deal found 8/26![Southwest logo]()
$159
This American Airlines deal was found by Cheapflights users on 8/27. 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 11/510:46 am -
2 stops23h 48m
Deal found 8/27![American Airlines logo]()
$160
This United Airlines deal was found by Cheapflights users on 8/27. 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 10/216:15 am -
2 stops13h 23m
Deal found 8/27![United Airlines logo]()
$164
This American Airlines deal was found by Cheapflights users on 8/27. 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 11/47:05 am -
2 stops25h 40m
Deal found 8/27![American Airlines logo]()
$165
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 28, 2026.
Round-trip from | $302 (American Airlines) |
|---|---|
One-way from | $119 (United 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 28, 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
Sat 9/19
5:00 am-8:38 pm
2 stops14h 38m
San Juan Luis Munoz Marin Intl
Tue 9/22
4:20 pm-11:37 pm
1 stop8h 17m
$306
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Tue 9/15
5:00 am-8:38 pm
2 stops14h 38m
San Juan Luis Munoz Marin Intl
Wed 9/16
7:00 am-5:09 pm
1 stop11h 09m
$323
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 10/31
10:48 am-11:36 pm
2 stops11h 48m
San Juan Luis Munoz Marin Intl
Sat 11/7
8:25 am-1:32 pm
1 stop7h 07m
$328
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Fri 10/9
2:25 pm-9:55 pm
1 stop6h 30m
San Juan Luis Munoz Marin Intl
Mon 10/12
8:50 pm-8:55 am
1 stop13h 05m
$340
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 10/12
8:05 pm-9:10 am
1 stop12h 05m
San Juan Luis Munoz Marin Intl
Sat 10/17
3:05 pm-9:25 pm
1 stop7h 20m
$342
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 1/9
12:14 pm-9:00 pm
1 stop6h 46m
San Juan Luis Munoz Marin Intl
Fri 1/15
2:05 am-9:46 am
1 stop9h 41m
$356
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
$366
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 12/6
6:18 pm-12:13 pm
2 stops16h 55m
Montego Bay Sangster Intl
Wed 12/9
2:54 pm-9:00 pm
1 stop7h 06m
$412
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 10/26
6:48 am-12:48 pm
1 stop6h 00m
Montego Bay Sangster Intl
Fri 10/30
2:01 pm-10:15 pm
1 stop8h 14m
$412
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Tue 1/26
5:55 am-3:25 pm
1 stop8h 30m
Montego Bay Sangster Intl
Tue 2/9
4:50 pm-11:49 pm
1 stop7h 59m
$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-AUA
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 28, 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
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
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 28, 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 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$356 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$213 | Average$600 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$244 | Average$574 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$699 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$735 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$465 | Average$567 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |