$119+ 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Oct 12 — Oct 191
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 September 12, 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 September 12, 2026.
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Mon 10/126:27 pm -
2 stops14h 19m
Fri 10/1612:41 pm -
1 stop12h 16m
Deal found 9/9![American Airlines logo]()
$238
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/56:27 pm -
1 stop16h 42m
Fri 10/306:00 am -
1 stop11h 57m
Deal found 9/8![American Airlines logo]()
$244
This American Airlines deal was found by Cheapflights users on 9/7. 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 11/187:17 am -
2 stops13h 22m
Fri 12/44:45 pm -
2 stops9h 10m
Deal found 9/7![American Airlines logo]()
$248
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop14h 38m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 9/8![Frontier logo]()
$264
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:15 am -
1 stop22h 03m
Sat 10/1710:39 am -
1 stop23h 41m
Deal found 9/8![Frontier logo]()
$268
This Priceline deal was found by Cheapflights users on 9/9. 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 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
Wed 10/143:00 am -
1 stop7h 20m
Deal found 9/9![Frontier logo]()
$269
This Justfly.com deal was found by Cheapflights users on 9/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop14h 35m
Mon 11/27:26 pm -
1 stop15h 50m
Deal found 9/8![Frontier logo]()
$271
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:15 am -
1 stop22h 03m
Wed 10/282:55 am -
1 stop7h 21m
Deal found 9/8![Frontier logo]()
$278
This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:15 am -
1 stop26h 28m
Mon 11/163:55 am -
1 stop7h 21m
Deal found 9/9![Frontier logo]()
$284
This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop27h 21m
Wed 10/213:00 am -
1 stop7h 20m
Deal found 9/9![Frontier logo]()
$301
This Delta deal was found by Cheapflights users on 9/10. 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 10/265:30 am -
1 stop9h 57m
Mon 11/25:44 pm -
1 stop7h 09m
Deal found 9/10![Delta logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/257:14 am -
1 stop8h 58m
Sun 11/11:02 pm -
1 stop11h 54m
Deal found 9/9![American Airlines logo]()
$417
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 September 12, 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 September 12, 2026.
This American Airlines deal was found by Cheapflights users on 9/7. 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 11/187:17 am -
2 stops13h 22m
Fri 12/48:30 am -
1 stop16h 25m
Deal found 9/7![American Airlines logo]()
$248
This United Airlines deal was found by Cheapflights users on 9/8. 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 -
1 stop7h 18m
Fri 1/152:05 am -
2 stops11h 50m
Deal found 9/8![United Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sat 11/710:20 am -
1 stop9h 00m
Tue 11/102:25 pm -
1 stop9h 00m
Deal found 9/11![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/75:50 pm -
2 stops17h 30m
Tue 3/96:00 pm -
1 stop16h 22m
Deal found 9/7![Delta logo]()
$418
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Sat 10/245:00 am -
1 stop8h 44m
Sat 10/317:05 am -
2 stops12h 53m
Deal found 9/12![United Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 9/10. 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 10/12:25 pm -
1 stop8h 55m
Mon 10/58:50 pm -
1 stop13h 05m
Deal found 9/10![Southwest logo]()
$395
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Tue 1/265:50 pm -
2 stops17h 36m
Tue 2/96:06 pm -
2 stops18h 24m
Deal found 9/11![American Airlines logo]()
$438
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Sat 1/3012:30 pm -
2 stops10h 06m
Sat 2/68:05 am -
2 stops10h 41m
Deal found 9/12![United Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 9/11. 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.
Tue 12/17:20 pm -
1 stop12h 35m
Sat 12/126:45 am -
1 stop7h 20m
Deal found 9/11![Southwest logo]()
$415
This Delta deal was found by Cheapflights users on 9/12. 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.
Mon 3/15:55 am -
1 stop8h 20m
Tue 3/92:55 pm -
1 stop8h 13m
Deal found 9/12![Delta logo]()
$482
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/283:09 pm -
2 stops20h 09m
Sun 11/13:59 pm -
1 stop7h 38m
Deal found 9/11![American Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/266:48 am -
1 stop6h 00m
Mon 11/22:54 pm -
1 stop6h 56m
Deal found 9/11![United Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 1/99:25 am -
2 stops9h 40m
Sat 1/166:55 am -
2 stops11h 10m
Deal found 9/8![Southwest logo]()
$445
This Delta deal was found by Cheapflights users on 9/8. 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.
Wed 1/205:55 am -
1 stop6h 40m
Wed 1/273:35 pm -
1 stop7h 33m
Deal found 9/8![Delta logo]()
$494
This United Airlines deal was found by Cheapflights users on 9/8. 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 12/19:15 am -
1 stop9h 45m
Sat 12/52:05 am -
2 stops11h 23m
Deal found 9/8![United Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 9/7. 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 2/196:38 pm -
2 stops18h 01m
Mon 2/224:29 pm -
1 stop8h 30m
Deal found 9/7![American Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 9/9. 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.
Mon 1/185:55 am -
1 stop6h 40m
Thu 2/43:35 pm -
1 stop7h 33m
Deal found 9/9![Delta logo]()
$494
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 10/246:38 pm -
1 stop16h 35m
Sat 10/312:20 pm -
1 stop8h 44m
Deal found 9/11![United Airlines logo]()
$432
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Thu 11/126:31 pm -
2 stops13h 59m
Fri 11/207:30 am -
2 stops11h 15m
Deal found 9/7![American Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 9/7. 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.
Sat 2/209:45 am -
1 stop11h 05m
Sun 2/286:10 am -
1 stop7h 35m
Deal found 9/7![Southwest logo]()
$509
This Delta deal was found by Cheapflights users on 9/10. 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.
Sun 1/35:30 am -
1 stop6h 20m
Fri 1/83:50 pm -
1 stop7h 39m
Deal found 9/10![Delta logo]()
$513
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 10/176:47 pm -
2 stops18h 43m
Sat 10/242:40 pm -
1 stop7h 57m
Deal found 9/11![United Airlines logo]()
$432
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Mon 1/185:04 am -
2 stops9h 49m
Thu 2/47:00 am -
2 stops15h 29m
Deal found 9/9![American Airlines logo]()
$498
This Southwest deal was found by Cheapflights users on 9/11. 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 10/265:00 am -
1 stop8h 05m
Mon 11/24:40 pm -
1 stop8h 50m
Deal found 9/11![Southwest logo]()
$519
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/97:00 am -
1 stop5h 40m
Thu 1/213:50 pm -
1 stop8h 59m
Deal found 9/7![Delta logo]()
$523
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Wed 2/246:00 am -
1 stop6h 46m
Mon 3/12:48 pm -
1 stop18h 18m
Deal found 9/11![United Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 10/286:02 pm -
2 stops18h 46m
Wed 11/43:05 pm -
2 stops10h 50m
Deal found 9/9![American Airlines logo]()
$503
This Southwest deal was found by Cheapflights users on 9/7. 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.
Sat 1/93:05 pm -
2 stops21h 40m
Thu 1/212:40 pm -
1 stop7h 10m
Deal found 9/7![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 9/9. 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.
Wed 1/205:55 am -
1 stop6h 40m
Mon 1/253:35 pm -
1 stop10h 14m
Deal found 9/9![Delta logo]()
$529
This United Airlines deal was found by Cheapflights users on 9/11. 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 12/17:00 am -
1 stop6h 40m
Sat 12/128:05 am -
2 stops12h 43m
Deal found 9/11![United Airlines logo]()
$440
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated September 12, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated September 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/56:27 pm -
1 stop16h 42m
Fri 10/306:00 am -
1 stop11h 57m
Deal found 9/8![American Airlines logo]()
$244
This Priceline deal was found by Cheapflights users on 9/9. 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 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
Wed 10/143:00 am -
1 stop7h 20m
Deal found 9/9![Frontier logo]()
$269
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Mon 10/126:27 pm -
2 stops14h 19m
Fri 10/1612:41 pm -
1 stop12h 16m
Deal found 9/9![American Airlines logo]()
$238
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:15 am -
1 stop22h 03m
Sat 10/1710:39 am -
1 stop23h 41m
Deal found 9/8![Frontier logo]()
$268
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop14h 38m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 9/8![Frontier logo]()
$264
This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop27h 21m
Wed 10/213:00 am -
1 stop7h 20m
Deal found 9/9![Frontier logo]()
$301
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:15 am -
1 stop22h 03m
Wed 10/282:55 am -
1 stop7h 21m
Deal found 9/8![Frontier logo]()
$278
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 10/217:19 pm -
2 stops19h 19m
Sat 10/3110:36 am -
2 stops26h 32m
Deal found 9/9![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 10/236:02 pm -
2 stops16h 29m
Sat 10/3110:36 am -
2 stops26h 32m
Deal found 9/9![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/257:14 am -
1 stop8h 58m
Sun 11/11:02 pm -
1 stop11h 54m
Deal found 9/9![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 9/10. 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 10/265:30 am -
1 stop9h 57m
Mon 11/25:44 pm -
1 stop7h 09m
Deal found 9/10![Delta logo]()
$412
This Justfly.com deal was found by Cheapflights users on 9/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop14h 35m
Mon 11/27:26 pm -
1 stop15h 50m
Deal found 9/8![Frontier logo]()
$271
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 September 12, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/126:10 am -
1 stop15h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$119
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/25:53 pm -
2 stops14h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$122
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/213:09 pm -
2 stops17h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/142:58 pm -
2 stops17h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$127
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Tue 10/275:10 pm -
2 stops15h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$129
This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop14h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$130
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/287:00 am -
2 stops14h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$134
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/176:27 pm -
2 stops16h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$135
This Priceline deal was found by Cheapflights users on 9/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:15 am -
1 stop22h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$140
This American Airlines deal was found by Cheapflights users on 9/10. 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 1/233:17 pm -
2 stops21h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 9/10. 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 1/227:41 pm -
2 stops18h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$155
This American Airlines deal was found by Cheapflights users on 9/10. 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 1/77:41 pm -
2 stops18h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![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 September 12, 2026.
Round-trip from | $238 (American Airlines) |
|---|---|
One-way from | $119 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $346 |
Good round-trip deal | $839 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 September 12, 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
Tue 10/13
5:10 pm-11:31 am
2 stops17h 21m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$125
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Tue 10/13
10:15 am-9:18 am
1 stop22h 03m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$140
MilwaukeeSaint Thomas Island
MKE Milwaukee-Mitchell - STT Saint Thomas Island Cyril E King
MKESTT
Milwaukee-Mitchell
Thu 1/7
7:41 pm-4:05 pm
2 stops18h 24m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$165
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Tue 10/6
5:30 am-4:49 pm
1 stop10h 19m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$168
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 9/28
5:30 am-1:01 pm
1 stop7h 31m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/30
6:52 am-5:06 pm
1 stop9h 14m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 9/27
5:30 am-1:01 pm
1 stop7h 31m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Wed 10/28
8:50 am-9:55 pm
1 stop12h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$183
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 11/16
8:10 am-12:45 am
2 stops14h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$183
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 1/11
10:27 am-9:00 pm
1 stop8h 33m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
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-NAS
MKE-STT
MKE-MBJ
MKE-PLS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to Caribbean
MKE-0CB
MKE-SJU
MKE-NAS
MKE-STT
MKE-MBJ
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $485). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $721). 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 September 12, 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
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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 September 12, 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 September 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$356 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$215 | Average$604 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$238 | Average$616 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$698 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$319 | Average$743 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$492 | Average$580 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$547 | Average$866 | FlexibilityNo cancel fee | On-time83% |