$146+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 13 — Nov 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 October 14, 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 October 14, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop27h 21m
Thu 12/33:59 pm -
1 stop26h 27m
Deal found 10/12![Frontier logo]()
$350
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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.
Tue 10/2010:15 am -
1 stop22h 03m
Thu 12/33:43 am -
1 stop14h 43m
Deal found 10/13![Frontier logo]()
$370
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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.
Thu 10/1510:15 am -
1 stop14h 38m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 10/10![Frontier logo]()
$396
This Southwest deal was found by Cheapflights users on 10/11. 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 11/710:50 am -
1 stop10h 45m
Tue 11/1010:45 am -
1 stop8h 35m
Deal found 10/11![Southwest logo]()
$406
This American Airlines deal was found by Cheapflights users on 10/11. 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 11/47:05 am -
1 stop15h 11m
Tue 11/103:53 pm -
1 stop9h 13m
Deal found 10/11![American Airlines logo]()
$411
This deal was found by Cheapflights users on 10/13. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:15 am -
1 stop11h 34m
Sat 11/287:17 am -
1 stop12h 09m
Deal found 10/13![Frontier logo]()
$413
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:15 pm -
2 stops10h 21m
Sat 12/122:05 am -
1 stop10h 09m
Deal found 10/13![United Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Tue 11/107:40 am -
2 stops11h 58m
Wed 11/183:53 pm -
2 stops10h 02m
Deal found 10/12![American Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 10/9. 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 11/612:45 pm -
2 stops10h 15m
Mon 11/95:50 pm -
1 stop7h 45m
Deal found 10/9![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:55 am -
1 stop6h 30m
Wed 12/93:25 pm -
1 stop6h 55m
Deal found 10/13![Southwest logo]()
$433
This American Airlines deal was found by Cheapflights users on 10/9. 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 12/62:51 pm -
1 stop23h 02m
Wed 12/91:24 pm -
1 stop10h 45m
Deal found 10/9![American Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/266:00 am -
1 stop29h 45m
Thu 12/31:24 pm -
1 stop11h 31m
Deal found 10/12![American Airlines logo]()
$440
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 October 14, 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 October 14, 2026.
This Southwest deal was found by Cheapflights users on 10/9. 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.
Thu 11/512:45 pm -
1 stop10h 25m
Tue 11/102:25 pm -
2 stops9h 55m
Deal found 10/9![Southwest logo]()
$406
This Delta deal was found by Cheapflights users on 10/12. 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 11/25:30 am -
1 stop9h 57m
Fri 11/63:26 pm -
1 stop6h 31m
Deal found 10/12![Delta logo]()
$433
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Wed 1/66:29 pm -
1 stop16h 44m
Wed 1/132:54 pm -
1 stop9h 21m
Deal found 10/9![United Airlines logo]()
$434
This American Airlines deal was found by Cheapflights users on 10/10. 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 11/277:33 pm -
1 stop17h 26m
Mon 12/74:38 pm -
1 stop8h 31m
Deal found 10/10![American Airlines logo]()
$510
This Southwest deal was found by Cheapflights users on 10/9. 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 11/147:05 am -
2 stops11h 25m
Fri 11/207:30 am -
1 stop9h 25m
Deal found 10/9![Southwest logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Sat 1/95:00 am -
2 stops10h 19m
Sat 1/165:21 pm -
2 stops17h 39m
Deal found 10/9![United Airlines logo]()
$438
This Southwest deal was found by Cheapflights users on 10/9. 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.
Wed 11/252:45 pm -
1 stop7h 35m
Wed 12/162:25 pm -
2 stops9h 50m
Deal found 10/9![Southwest logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Tue 1/125:00 am -
1 stop7h 48m
Sat 1/163:45 pm -
2 stops17h 22m
Deal found 10/12![United Airlines logo]()
$438
This Southwest deal was found by Cheapflights users on 10/12. 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.
Fri 12/47:20 pm -
1 stop12h 40m
Thu 12/105:40 am -
1 stop7h 10m
Deal found 10/12![Southwest logo]()
$406
This Delta deal was found by Cheapflights users on 10/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/45:55 am -
1 stop7h 10m
Sun 2/71:50 pm -
1 stop11h 59m
Deal found 10/11![Delta logo]()
$502
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Sun 1/315:50 pm -
2 stops19h 49m
Thu 2/41:44 pm -
2 stops11h 15m
Deal found 10/12![American Airlines logo]()
$524
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Sat 1/165:00 am -
2 stops10h 19m
Wed 1/202:54 pm -
1 stop7h 05m
Deal found 10/9![United Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 10/12. 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.
Sun 1/315:55 am -
1 stop7h 30m
Thu 2/43:50 pm -
1 stop8h 59m
Deal found 10/12![Delta logo]()
$520
This Southwest deal was found by Cheapflights users on 10/9. 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 11/67:50 pm -
1 stop13h 30m
Mon 11/95:50 pm -
1 stop7h 45m
Deal found 10/9![Southwest logo]()
$431
This American Airlines deal was found by Cheapflights users on 10/9. 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 1/205:00 am -
1 stop8h 39m
Wed 2/31:44 pm -
2 stops11h 15m
Deal found 10/9![American Airlines logo]()
$529
This Southwest deal was found by Cheapflights users on 10/9. 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.
Mon 11/26:55 am -
1 stop6h 30m
Fri 11/61:00 pm -
1 stop11h 35m
Deal found 10/9![Southwest logo]()
$433
This United Airlines deal was found by Cheapflights users on 10/12. 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 2/216:45 pm -
1 stop16h 28m
Wed 2/242:54 pm -
1 stop18h 12m
Deal found 10/12![United Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 10/10. 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 10/315:30 am -
1 stop7h 10m
Sat 11/74:05 pm -
1 stop9h 48m
Deal found 10/10![Delta logo]()
$539
This American Airlines deal was found by Cheapflights users on 10/11. 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 12/55:50 pm -
2 stops19h 55m
Sat 12/128:15 am -
2 stops15h 54m
Deal found 10/11![American Airlines logo]()
$564
This Southwest deal was found by Cheapflights users on 10/10. 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 12/66:55 am -
1 stop6h 30m
Wed 12/93:25 pm -
1 stop6h 55m
Deal found 10/10![Southwest logo]()
$433
This Delta deal was found by Cheapflights users on 10/9. 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 3/37:00 am -
1 stop6h 25m
Tue 3/93:50 pm -
1 stop8h 59m
Deal found 10/9![Delta logo]()
$542
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/186:00 am -
1 stop8h 20m
Mon 1/253:00 pm -
1 stop10h 15m
Deal found 10/13![United Airlines logo]()
$496
This Delta deal was found by Cheapflights users on 10/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/305:55 am -
1 stop8h 05m
Fri 2/51:40 pm -
1 stop9h 28m
Deal found 10/11![Delta logo]()
$547
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:48 am -
2 stops9h 34m
Tue 11/102:05 am -
2 stops13h 27m
Deal found 10/13![United Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/72:55 pm -
2 stops21h 35m
Thu 11/125:59 pm -
2 stops18h 03m
Deal found 10/14![American Airlines logo]()
$615
This Southwest deal was found by Cheapflights users on 10/11. 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 10/3010:25 am -
1 stop10h 30m
Sun 11/15:50 pm -
1 stop7h 40m
Deal found 10/11![Southwest logo]()
$501
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/175:55 am -
1 stop7h 30m
Sun 1/242:15 pm -
1 stop10h 34m
Deal found 10/13![Delta logo]()
$552
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Sun 11/297:33 pm -
2 stops14h 39m
Sat 12/52:37 pm -
2 stops9h 32m
Deal found 10/13![American Airlines logo]()
$621
This United Airlines deal was found by Cheapflights users on 10/11. 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 11/186:47 am -
2 stops13h 35m
Thu 11/262:52 pm -
1 stop9h 58m
Deal found 10/11![United Airlines logo]()
$535
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/175:55 am -
1 stop7h 30m
Sat 1/233:05 pm -
1 stop7h 04m
Deal found 10/13![Delta logo]()
$552
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated October 14, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop27h 21m
Thu 12/33:59 pm -
1 stop26h 27m
Deal found 10/12![Frontier logo]()
$350
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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.
Thu 10/1510:15 am -
1 stop14h 38m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 10/9![Frontier logo]()
$396
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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.
Tue 10/2010:15 am -
1 stop22h 03m
Thu 12/33:43 am -
1 stop14h 43m
Deal found 10/13![Frontier logo]()
$370
This Southwest deal was found by Cheapflights users on 10/9. 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.
Mon 11/26:55 am -
1 stop6h 30m
Fri 11/61:00 pm -
1 stop11h 35m
Deal found 10/9![Southwest logo]()
$433
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/27:29 pm -
2 stops15h 52m
Fri 11/66:09 pm -
2 stops14h 39m
Deal found 10/9![American Airlines logo]()
$437
This American Airlines deal was found by Cheapflights users on 10/11. 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 11/47:05 am -
1 stop15h 11m
Tue 11/101:00 pm -
2 stops11h 37m
Deal found 10/11![American Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 10/9. 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.
Thu 11/512:45 pm -
2 stops10h 15m
Tue 11/102:25 pm -
2 stops9h 55m
Deal found 10/9![Southwest logo]()
$445
This Southwest deal was found by Cheapflights users on 10/9. 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 11/612:45 pm -
2 stops10h 15m
Mon 11/95:50 pm -
1 stop7h 45m
Deal found 10/9![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 10/11. 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 11/710:50 am -
1 stop10h 45m
Tue 11/1010:45 am -
1 stop8h 35m
Deal found 10/11![Southwest logo]()
$406
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Tue 11/107:40 am -
2 stops11h 58m
Wed 11/183:53 pm -
2 stops10h 02m
Deal found 10/12![American Airlines logo]()
$421
This deal was found by Cheapflights users on 10/13. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:15 am -
1 stop11h 34m
Sat 11/287:17 am -
1 stop12h 09m
Deal found 10/13![Frontier logo]()
$413
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/266:00 am -
1 stop29h 45m
Thu 12/31:24 pm -
1 stop11h 31m
Deal found 10/12![American Airlines logo]()
$440
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 October 14, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/75:24 pm -
2 stops29h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$146
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/305:55 am -
1 stop8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$192
This American Airlines deal was found by Cheapflights users on 10/11. 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 2/155:43 pm -
2 stops17h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![American Airlines logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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.
Tue 10/2010:15 am -
1 stop14h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$198
This American Airlines deal was found by Cheapflights users on 10/10. 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 1/231:38 pm -
1 stop8h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![American Airlines logo]()
$203
This American Airlines deal was found by Cheapflights users on 10/9. 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 1/308:03 pm -
1 stop18h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![American Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 10/12. 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 12/27:09 am -
1 stop12h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![American Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 10/11. 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 11/306:25 pm -
2 stops13h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![American Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/288:15 am -
2 stops30h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$212
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:20 pm -
1 stop13h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$213
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Tue 12/159:15 am -
2 stops13h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![United Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/85:55 am -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$225
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 October 14, 2026.
Round-trip from | $382 (United Airlines) |
|---|---|
One-way from | $146 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $399 |
Good round-trip deal | $425 or less |
Good one-way deal | $375 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 October 14, 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
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/30
5:55 am-3:25 pm
1 stop8h 30m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$192
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/30
3:34 pm-12:18 pm
2 stops19h 44m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$192
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 2/15
6:45 pm-2:14 pm
1 stop18h 29m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$192
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 11/1
2:55 pm-10:15 am
2 stops18h 20m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$192
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 2/15
5:43 pm-12:12 pm
2 stops17h 29m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$198
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Wed 12/2
2:15 pm-12:50 am
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$203
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 11/16
7:20 pm-9:55 am
1 stop12h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$203
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Wed 11/11
8:00 am-9:24 pm
2 stops11h 24m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$203
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 2/8
8:05 am-11:40 pm
2 stops13h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$203
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 12/14
7:00 am-10:22 pm
2 stops13h 22m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$203
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-SXM
MKE-NAS
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-MBJ
MKE-SXM
MKE-NAS
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 $476). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $747). 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 October 14, 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
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
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 October 14, 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 October 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$336 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$607 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$238 | Average$636 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$644 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$273 | Average$548 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$321 | Average$719 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$488 | Average$834 | FlexibilityNo cancel fee | On-time83% |