$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 10 — Sep 171
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Caribbean with Cheapflights
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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 11, 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 11, 2026.
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/112:02 pm -
2 stops18h 22m
Fri 9/1810:16 am -
2 stops11h 54m
Deal found 8/11![American Airlines logo]()
$238
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Wed 9/22:49 pm -
1 stop8h 10m
Wed 9/911:51 am -
2 stops11h 03m
Deal found 8/10![American Airlines logo]()
$243
This Faresmojo deal was found by Cheapflights users on 8/10. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:05 am -
1 stop8h 44m
Fri 10/305:59 pm -
1 stop6h 54m
Deal found 8/10![JetBlue logo]()
$265
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 9/241:55 pm -
1 stop7h 20m
Tue 9/298:20 am -
1 stop9h 00m
Deal found 8/10![Southwest logo]()
$292
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Mon 8/316:28 am -
1 stop7h 23m
Thu 9/106:00 am -
2 stops16h 48m
Deal found 8/10![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Wed 9/212:58 pm -
1 stop8h 26m
Fri 9/112:22 pm -
1 stop7h 48m
Deal found 8/10![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Mon 9/75:00 am -
1 stop17h 15m
Sat 9/193:41 pm -
2 stops17h 20m
Deal found 8/11![American Airlines logo]()
$317
This Faresmojo deal was found by Cheapflights users on 8/11. 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 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 8/11![JetBlue logo]()
$319
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 9/2112:30 pm -
2 stops9h 40m
Tue 9/298:20 am -
1 stop9h 00m
Deal found 8/11![Southwest logo]()
$320
This American Airlines deal was found by Cheapflights users on 8/11. 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 10/317:19 pm -
2 stops19h 33m
Sat 11/76:28 am -
1 stop7h 20m
Deal found 8/11![American Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com 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 9/910:42 am -
1 stop23h 26m
Deal found 8/9![Frontier logo]()
$335
This American Airlines deal was found by Cheapflights users on 8/11. 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 10/287:00 am -
1 stop7h 01m
Sat 11/76:28 am -
1 stop17h 32m
Deal found 8/11![American Airlines logo]()
$337
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 11, 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 11, 2026.
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 9/1112:30 pm -
1 stop9h 25m
Fri 9/1811:35 am -
1 stop10h 15m
Deal found 8/11![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 8/8. 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 10/55:30 am -
1 stop7h 15m
Fri 10/305:59 pm -
1 stop6h 54m
Deal found 8/8![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/11. 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.
Mon 9/285:00 am -
1 stop8h 44m
Sun 10/43:56 pm -
1 stop8h 03m
Deal found 8/11![United Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Thu 9/242:02 pm -
1 stop21h 25m
Thu 10/112:36 pm -
1 stop6h 57m
Deal found 8/10![American Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 10/22:25 pm -
1 stop6h 30m
Mon 10/55:35 pm -
1 stop7h 10m
Deal found 8/11![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 9/2112:30 pm -
2 stops9h 40m
Tue 9/298:20 am -
1 stop9h 00m
Deal found 8/11![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 8/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:28 am -
1 stop7h 07m
Wed 11/182:20 pm -
1 stop10h 34m
Deal found 8/9![Delta logo]()
$392
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 1/306:00 am -
2 stops9h 24m
Sat 2/63:20 pm -
1 stop8h 26m
Deal found 8/7![United Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 8/9. 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.
Sun 9/202:10 pm -
1 stop9h 25m
Tue 9/221:20 pm -
2 stops9h 00m
Deal found 8/9![Southwest logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 2/35:00 am -
1 stop8h 35m
Sun 2/73:25 pm -
1 stop8h 17m
Deal found 8/6![American Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 8/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:28 am -
1 stop7h 07m
Thu 11/192:20 pm -
1 stop7h 43m
Deal found 8/9![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/411:00 am -
1 stop11h 10m
Sun 9/66:30 am -
1 stop8h 25m
Deal found 8/7![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 1/237:00 am -
1 stop5h 45m
Sat 1/305:30 pm -
2 stops17h 19m
Deal found 8/7![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 8/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:28 am -
1 stop7h 07m
Tue 11/171:50 pm -
2 stops20h 00m
Deal found 8/9![Delta logo]()
$397
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Mon 11/306:31 pm -
1 stop17h 26m
Tue 12/83:26 pm -
2 stops21h 42m
Deal found 8/10![American Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 8/8. 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.
Sun 9/63:20 pm -
1 stop6h 50m
Mon 9/146:00 am -
1 stop11h 10m
Deal found 8/8![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/11. 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.
Mon 11/166:18 pm -
2 stops16h 31m
Sat 11/214:00 pm -
1 stop5h 50m
Deal found 8/11![United Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 8/9. 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 2/43:49 pm -
1 stop19h 56m
Fri 2/125:33 pm -
2 stops16h 34m
Deal found 8/9![American Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 9/145:35 am -
1 stop7h 10m
Tue 9/2210:30 am -
1 stop6h 50m
Deal found 8/10![Southwest logo]()
$374
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Sat 12/57:40 am -
1 stop6h 01m
Sat 12/128:15 am -
2 stops14h 45m
Deal found 8/10![American Airlines logo]()
$483
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/215:30 am -
1 stop7h 23m
Sat 9/263:18 pm -
1 stop9h 30m
Deal found 8/6![Delta logo]()
$492
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 10/276:47 am -
1 stop6h 01m
Thu 10/292:20 pm -
1 stop8h 30m
Deal found 8/6![United Airlines logo]()
$492
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 10/112:20 pm -
1 stop10h 45m
Fri 10/96:30 am -
1 stop12h 20m
Deal found 8/10![Southwest logo]()
$374
This American Airlines deal was found by Cheapflights users on 8/11. 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 11/187:17 am -
1 stop5h 46m
Sun 11/223:14 pm -
2 stops19h 50m
Deal found 8/11![American Airlines logo]()
$487
This United Airlines deal was found by Cheapflights users on 8/8. 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.
Mon 10/266:18 pm -
2 stops16h 55m
Thu 10/2912:25 pm -
2 stops21h 48m
Deal found 8/8![United Airlines logo]()
$497
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/197:00 am -
1 stop5h 23m
Sat 10/242:23 pm -
1 stop10h 34m
Deal found 8/7![American Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 8/8. 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.
Sat 12/57:00 am -
1 stop5h 45m
Sat 12/123:10 pm -
1 stop8h 08m
Deal found 8/8![Delta logo]()
$541
This United Airlines deal was found by Cheapflights users on 8/10. 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.
Fri 9/257:18 am -
2 stops30h 12m
Fri 10/212:52 pm -
2 stops18h 15m
Deal found 8/10![United Airlines logo]()
$512
This Delta deal was found by Cheapflights users on 8/10. 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.
Tue 9/155:30 am -
1 stop6h 10m
Sun 9/202:05 pm -
1 stop8h 25m
Deal found 8/10![Delta logo]()
$543
This American Airlines deal was found by Cheapflights users on 8/11. 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 11/117:17 am -
1 stop29h 13m
Tue 11/175:33 pm -
2 stops19h 35m
Deal found 8/11![American Airlines logo]()
$513
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated August 11, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated August 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com 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 9/910:42 am -
1 stop23h 26m
Deal found 8/9![Frontier logo]()
$335
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Mon 8/316:28 am -
1 stop7h 23m
Thu 9/106:00 am -
2 stops16h 48m
Deal found 8/10![American Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:10 pm -
1 stop13h 05m
Sat 9/129:50 pm -
1 stop12h 32m
Deal found 8/10![Frontier logo]()
$341
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Wed 9/22:49 pm -
1 stop8h 10m
Wed 9/911:51 am -
2 stops11h 03m
Deal found 8/10![American Airlines logo]()
$243
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Wed 9/212:58 pm -
1 stop8h 26m
Fri 9/112:22 pm -
1 stop7h 48m
Deal found 8/10![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Mon 9/75:00 am -
1 stop17h 15m
Sat 9/193:41 pm -
2 stops17h 20m
Deal found 8/11![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/112:02 pm -
2 stops18h 22m
Fri 9/182:22 pm -
1 stop7h 48m
Deal found 8/11![American Airlines logo]()
$238
This United Airlines deal was found by Cheapflights users on 8/8. 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.
Tue 9/1512:05 pm -
2 stops23h 38m
Tue 9/2212:52 pm -
1 stop10h 45m
Deal found 8/8![United Airlines logo]()
$397
This Faresmojo deal was found by Cheapflights users on 8/11. 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 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 8/11![JetBlue logo]()
$319
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 9/2112:30 pm -
2 stops9h 40m
Tue 9/298:20 am -
1 stop9h 00m
Deal found 8/11![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 9/241:55 pm -
1 stop7h 20m
Tue 9/298:20 am -
1 stop9h 00m
Deal found 8/10![Southwest logo]()
$292
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Thu 9/245:11 pm -
2 stops16h 49m
Mon 9/286:00 am -
2 stops14h 33m
Deal found 8/11![American Airlines logo]()
$332
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 11, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 11, 2026.
This American Airlines deal was found by Cheapflights users on 8/11. 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 10/176:27 pm -
2 stops14h 19m
Deal found 8/11![American Airlines logo]()
$119
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/212:58 pm -
1 stop8h 26m
Deal found 8/11![American Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Mon 9/218:14 pm -
2 stops17h 36m
Deal found 8/11![American Airlines logo]()
$125
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Sat 10/106:10 am -
2 stops12h 50m
Deal found 8/10![American Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:10 pm -
1 stop28h 33m
Deal found 8/11![Frontier logo]()
$162
This American Airlines deal was found by Cheapflights users on 8/11. 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 1/305:28 pm -
2 stops18h 30m
Deal found 8/11![American Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 8/10. 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.
Mon 9/212:55 pm -
1 stop6h 24m
Deal found 8/10![Delta logo]()
$173
This United Airlines deal was found by Cheapflights users on 8/9. 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 9/112:20 pm -
2 stops21h 23m
Deal found 8/9![United Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/96:27 pm -
2 stops16h 04m
Deal found 8/7![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/92:48 pm -
2 stops17h 36m
Deal found 8/7![American Airlines logo]()
$182
This Frontier deal was found by Cheapflights users on 8/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:10 pm -
1 stop13h 05m
Deal found 8/11![Frontier logo]()
$198
This Southwest deal was found by Cheapflights users on 8/8. 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.
Mon 9/1412:30 pm -
1 stop9h 25m
Deal found 8/8![Southwest logo]()
$201
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 11, 2026.
Round-trip from | $238 (American Airlines) |
|---|---|
One-way from | $119 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $414 |
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 2,558,603 searches. Data last updated August 11, 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
Fri 9/11
12:30 pm-10:55 pm
1 stop9h 25m
San Juan Luis Munoz Marin Intl
Fri 9/18
11:35 am-8:50 pm
1 stop10h 15m
$292
Quickest round-trip
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Fri 10/2
2:25 pm-9:55 pm
1 stop6h 30m
San Juan Luis Munoz Marin Intl
Mon 10/5
5:35 pm-11:45 pm
1 stop7h 10m
$292
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 9/21
12:30 pm-11:10 pm
2 stops9h 40m
San Juan Luis Munoz Marin Intl
Tue 9/29
8:20 am-4:20 pm
1 stop9h 00m
$320
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 10/5
5:30 am-1:45 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Fri 10/30
5:59 pm-11:53 pm
1 stop6h 54m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 9/28
5:00 am-2:44 pm
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Sun 10/4
3:56 pm-10:59 pm
1 stop8h 03m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sun 9/20
2:10 pm-12:35 am
1 stop9h 25m
San Juan Luis Munoz Marin Intl
Tue 9/22
1:20 pm-9:20 pm
2 stops9h 00m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Fri 9/4
11:00 am-11:10 pm
1 stop11h 10m
San Juan Luis Munoz Marin Intl
Sun 9/6
6:30 am-1:55 pm
1 stop8h 25m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sun 9/6
3:20 pm-11:10 pm
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Mon 9/14
6:00 am-4:10 pm
1 stop11h 10m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 9/14
5:35 am-1:45 pm
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Tue 9/22
10:30 am-4:20 pm
1 stop6h 50m
$374
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 10/1
12:20 pm-12:05 am
1 stop10h 45m
San Juan Luis Munoz Marin Intl
Fri 10/9
6:30 am-5:50 pm
1 stop12h 20m
$374
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Milwaukee with our price prediction graph.
MKE-SJU
MKE-MBJ
MKE-GCM
MKE-SXM
MKE-NAS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to Caribbean
MKE-0CB
MKE-SJU
MKE-MBJ
MKE-GCM
MKE-SXM
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $471). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $725). 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 11, 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.
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
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 11, 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 2,558,603 searches. Data last updated August 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$170 | Average$594 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$567 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$644 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$318 | Average$718 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$465 | Average$567 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$547 | Average$853 | FlexibilityNo cancel fee | On-time83% |