$152+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Dec 13 — Dec 201
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 November 13, 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 13, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/10. 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.
Fri 12/45:24 pm -
1 stop6h 47m
Mon 12/711:48 am -
1 stop7h 30m
Deal found 11/10![Frontier logo]()
$396
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Mon 11/306:11 pm -
1 stop14h 29m
Thu 12/38:44 pm -
1 stop21h 42m
Deal found 11/11![Frontier logo]()
$399
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/55:00 am -
1 stop9h 07m
Sat 12/122:52 pm -
1 stop9h 17m
Deal found 11/12![American Airlines logo]()
$418
This Southwest deal was found by Cheapflights users on 11/9. 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 12/1112:35 pm -
1 stop10h 35m
Sat 12/197:15 pm -
1 stop7h 05m
Deal found 11/9![Southwest logo]()
$436
This American Airlines deal was found by Cheapflights users on 11/11. 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
Wed 12/93:53 pm -
2 stops10h 06m
Deal found 11/11![American Airlines logo]()
$441
This American Airlines deal was found by Cheapflights users on 11/8. 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 11/306:25 pm -
2 stops13h 13m
Sat 12/51:54 pm -
2 stops10h 43m
Deal found 11/8![American Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 11/12. 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 11/2610:20 am -
1 stop5h 37m
Wed 12/26:12 pm -
1 stop16h 01m
Deal found 11/12![Delta logo]()
$452
This American Airlines deal was found by Cheapflights users on 11/11. 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
Sat 12/51:54 pm -
1 stop11h 15m
Deal found 11/11![American Airlines logo]()
$459
This Cheapflightsfares deal was found by Cheapflights users on 11/9. 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.
Fri 11/206:11 pm -
1 stop27h 07m
Sun 11/293:55 am -
1 stop15h 31m
Deal found 11/9![Frontier logo]()
$460
This Delta deal was found by Cheapflights users on 11/8. 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 11/295:20 am -
1 stop6h 31m
Wed 12/162:19 pm -
1 stop7h 38m
Deal found 11/8![Delta logo]()
$463
This Southwest deal was found by Cheapflights users on 11/11. 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 stops11h 45m
Wed 12/92:25 pm -
2 stops9h 55m
Deal found 11/11![Southwest logo]()
$465
This Southwest deal was found by Cheapflights users on 11/9. 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
Sat 12/127:45 am -
1 stop12h 35m
Deal found 11/9![Southwest logo]()
$466
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 13, 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 13, 2026.
This American Airlines deal was found by Cheapflights users on 11/9. 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 2/65:17 am -
1 stop8h 23m
Thu 2/113:54 pm -
1 stop8h 10m
Deal found 11/9![American Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 11/8. 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 11/8![Delta logo]()
$436
This Southwest deal was found by Cheapflights users on 11/12. 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 12/108:10 am -
2 stops14h 40m
Thu 12/174:00 pm -
2 stops9h 10m
Deal found 11/12![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 11/12. 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 2/2810:41 am -
2 stops9h 41m
Fri 3/58:05 am -
2 stops10h 38m
Deal found 11/12![United Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 11/10. 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
Mon 12/72:25 pm -
2 stops9h 55m
Deal found 11/10![Southwest logo]()
$436
This Delta deal was found by Cheapflights users on 11/8. 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 1/176:26 am -
1 stop7h 41m
Wed 1/206:35 pm -
1 stop7h 24m
Deal found 11/8![Delta logo]()
$436
This United Airlines deal was found by Cheapflights users on 11/10. 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 3/15:55 pm -
2 stops17h 18m
Mon 3/152:45 pm -
2 stops17h 17m
Deal found 11/10![United Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 11/8. 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 11/295:20 am -
1 stop6h 31m
Wed 12/162:19 pm -
1 stop7h 38m
Deal found 11/8![Delta logo]()
$463
This Southwest deal was found by Cheapflights users on 11/12. 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 1/2111:30 am -
1 stop8h 30m
Sat 1/306:05 am -
1 stop8h 05m
Deal found 11/12![Southwest logo]()
$465
This United Airlines deal was found by Cheapflights users on 11/8. 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 1/95:00 am -
2 stops10h 19m
Sat 1/163:45 pm -
2 stops17h 22m
Deal found 11/8![United Airlines logo]()
$480
This American Airlines deal was found by Cheapflights users on 11/10. 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 1/1512:35 pm -
2 stops8h 47m
Fri 1/222:45 pm -
2 stops8h 51m
Deal found 11/10![American Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 11/12. 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 stop8h 44m
Tue 2/96:09 pm -
1 stop6h 50m
Deal found 11/12![Delta logo]()
$464
This American Airlines deal was found by Cheapflights users on 11/12. 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 2/42:09 pm -
2 stops20h 15m
Sun 2/75:04 pm -
2 stops18h 15m
Deal found 11/12![American Airlines logo]()
$538
This Delta deal was found by Cheapflights users on 11/12. 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 1/233:36 pm -
2 stops19h 47m
Sat 1/303:35 pm -
2 stops18h 44m
Deal found 11/12![Delta logo]()
$468
This Southwest deal was found by Cheapflights users on 11/12. 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 12/210:45 am -
1 stop9h 40m
Fri 12/47:40 am -
1 stop9h 50m
Deal found 11/12![Southwest logo]()
$526
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/286:45 am -
1 stop7h 05m
Thu 12/32:18 pm -
1 stop11h 37m
Deal found 11/12![American Airlines logo]()
$544
This United Airlines deal was found by Cheapflights users on 11/11. 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 4/67:00 am -
1 stop5h 45m
Mon 4/121:50 pm -
1 stop8h 49m
Deal found 11/11![United Airlines logo]()
$565
This Southwest deal was found by Cheapflights users on 11/10. 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 1/105:15 am -
1 stop7h 40m
Sun 1/173:45 pm -
2 stops18h 40m
Deal found 11/10![Southwest logo]()
$529
This American Airlines deal was found by Cheapflights users on 11/8. 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 11/286:45 am -
2 stops14h 09m
Wed 12/211:53 am -
1 stop12h 16m
Deal found 11/8![American Airlines logo]()
$551
This United Airlines deal was found by Cheapflights users on 11/8. 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 2/35:00 am -
1 stop7h 45m
Sun 2/72:55 pm -
1 stop7h 04m
Deal found 11/8![United Airlines logo]()
$565
This Delta deal was found by Cheapflights users on 11/12. 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 1/276:43 pm -
1 stop17h 06m
Fri 1/296:09 pm -
1 stop6h 50m
Deal found 11/12![Delta logo]()
$523
This Southwest deal was found by Cheapflights users on 11/9. 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 1/305:50 am -
1 stop6h 00m
Sat 1/303:20 pm -
1 stop7h 30m
Deal found 11/9![Southwest logo]()
$539
This American Airlines deal was found by Cheapflights users on 11/9. 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 1/36:49 pm -
1 stop15h 38m
Thu 1/710:31 am -
2 stops10h 01m
Deal found 11/9![American Airlines logo]()
$551
This United Airlines deal was found by Cheapflights users on 11/9. 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 12/256:40 am -
1 stop6h 05m
Thu 12/312:55 pm -
1 stop9h 16m
Deal found 11/9![United Airlines logo]()
$565
This Delta deal was found by Cheapflights users on 11/12. 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 1/232:59 pm -
2 stops20h 24m
Sun 1/313:35 pm -
2 stops19h 22m
Deal found 11/12![Delta logo]()
$527
This American Airlines deal was found by Cheapflights users on 11/9. 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 11/297:33 pm -
2 stops14h 39m
Sat 12/512:09 pm -
1 stop12h 00m
Deal found 11/9![American Airlines logo]()
$551
This United Airlines deal was found by Cheapflights users on 11/9. 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 12/256:40 am -
1 stop6h 05m
Wed 12/302:55 pm -
1 stop7h 01m
Deal found 11/9![United Airlines logo]()
$565
This Southwest deal was found by Cheapflights users on 11/8. 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 2/511:40 am -
2 stops7h 35m
Sat 2/135:35 am -
2 stops10h 15m
Deal found 11/8![Southwest logo]()
$573
This Delta deal was found by Cheapflights users on 11/8. 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 1/47:00 am -
1 stop6h 49m
Wed 1/131:54 pm -
1 stop12h 05m
Deal found 11/8![Delta logo]()
$529
This American Airlines deal was found by Cheapflights users on 11/9. 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 2/2011:50 am -
1 stop13h 04m
Deal found 11/9![American Airlines logo]()
$553
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated November 13, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated November 13, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 11/9. 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.
Fri 11/206:11 pm -
1 stop27h 07m
Sun 11/293:55 am -
1 stop15h 31m
Deal found 11/9![Frontier logo]()
$460
This Delta deal was found by Cheapflights users on 11/12. 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 11/2610:20 am -
1 stop5h 37m
Wed 12/26:12 pm -
1 stop16h 01m
Deal found 11/12![Delta logo]()
$452
This Delta deal was found by Cheapflights users on 11/8. 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 11/295:20 am -
1 stop6h 31m
Wed 12/162:19 pm -
1 stop7h 38m
Deal found 11/8![Delta logo]()
$463
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Mon 11/306:11 pm -
1 stop14h 29m
Thu 12/38:44 pm -
1 stop21h 42m
Deal found 11/11![Frontier logo]()
$399
This American Airlines deal was found by Cheapflights users on 11/8. 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 11/306:25 pm -
2 stops13h 13m
Sat 12/51:54 pm -
2 stops10h 43m
Deal found 11/8![American Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 11/11. 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
Wed 12/93:53 pm -
2 stops10h 06m
Deal found 11/11![American Airlines logo]()
$441
This American Airlines deal was found by Cheapflights users on 11/11. 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
Sat 12/51:54 pm -
1 stop11h 15m
Deal found 11/11![American Airlines logo]()
$459
This Southwest deal was found by Cheapflights users on 11/11. 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 stops11h 45m
Wed 12/92:25 pm -
2 stops9h 55m
Deal found 11/11![Southwest logo]()
$465
This Cheapflightsfares deal was found by Cheapflights users on 11/10. 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.
Fri 12/45:24 pm -
1 stop6h 47m
Mon 12/711:48 am -
1 stop7h 30m
Deal found 11/10![Frontier logo]()
$396
This Southwest deal was found by Cheapflights users on 11/9. 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
Sat 12/127:45 am -
1 stop12h 35m
Deal found 11/9![Southwest logo]()
$466
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/55:00 am -
1 stop9h 07m
Sat 12/122:52 pm -
1 stop9h 17m
Deal found 11/12![American Airlines logo]()
$418
This Southwest deal was found by Cheapflights users on 11/9. 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 12/1112:35 pm -
1 stop10h 35m
Sat 12/197:15 pm -
1 stop7h 05m
Deal found 11/9![Southwest logo]()
$436
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 13, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 13, 2026.
This American Airlines deal was found by Cheapflights users on 11/11. 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 1/912:10 pm -
2 stops22h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![American Airlines logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 11/13. 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.
Mon 12/76:13 pm -
1 stop14h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![Frontier logo]()
$157
This Delta deal was found by Cheapflights users on 11/10. 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 1/305:30 am -
1 stop10h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$207
This American Airlines deal was found by Cheapflights users on 11/9. 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 1/306:24 am -
1 stop6h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![American Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 11/10. 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 12/235:30 am -
1 stop6h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$215
This American Airlines deal was found by Cheapflights users on 11/11. 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 1/85:50 pm -
2 stops17h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![American Airlines logo]()
$218
This American Airlines deal was found by Cheapflights users on 11/13. 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 1/236:07 am -
2 stops13h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![American Airlines logo]()
$218
This American Airlines deal was found by Cheapflights users on 11/9. 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 3/308:50 am -
1 stop14h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![American Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 11/9. 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 12/106:00 am -
2 stops13h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/316:50 am -
1 stop15h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![American Airlines logo]()
$225
This American Airlines deal was found by Cheapflights users on 11/13. 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 12/77:09 am -
1 stop12h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![American Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/306:49 pm -
1 stop14h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![American Airlines logo]()
$230
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 13, 2026.
Round-trip from | $316 (Cheapflightsfares) |
|---|---|
One-way from | $152 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $501 |
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 13, 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
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Sat 1/9
12:10 pm-12:34 pm
2 stops22h 24m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$152
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Fri 1/8
7:00 am-4:44 pm
1 stop8h 44m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/30
5:30 am-4:44 pm
1 stop10h 14m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/30
3:34 pm-12:28 pm
2 stops19h 54m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$212
MilwaukeeNassau
MKE Milwaukee-Mitchell - NAS Nassau Intl
MKENAS
Milwaukee-Mitchell
Wed 12/23
5:30 am-1:28 pm
1 stop6h 58m
Nassau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$215
MilwaukeeNassau
MKE Milwaukee-Mitchell - NAS Nassau Intl
MKENAS
Milwaukee-Mitchell
Thu 12/24
5:30 am-1:28 pm
1 stop6h 58m
Nassau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$215
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 1/9
3:51 pm-6:15 am
2 stops12h 24m
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
Fri 1/15
9:05 am-11:35 pm
1 stop12h 30m
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 2/18
7:55 pm-10:00 am
1 stop12h 05m
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
Tue 1/5
5:00 am-3:40 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$218
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-GCM
MKE-MBJ
MKE-SXM
MKE-PUJ
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-GCM
MKE-MBJ
MKE-SXM
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $496). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $744). 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 13, 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.
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
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 13, 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 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$587 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$679 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$660 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$273 | Average$548 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$323 | Average$720 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$488 | Average$868 | FlexibilityNo cancel fee | On-time83% |