$152+ Cheap flights from Milwaukee (MKE) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Oct 17 — Oct 241
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Milwaukee to Caribbean
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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 17, 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 17, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/810:15 am -
1 stop11h 50m
Wed 10/146:42 pm -
1 stop15h 38m
Deal found 9/17![Frontier logo]()
$284
This Priceline deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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
Sat 10/103:00 am -
1 stop7h 20m
Deal found 9/16![Frontier logo]()
$308
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop14h 38m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 9/15![Frontier logo]()
$311
This FlightHub deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop14h 35m
Mon 11/211:20 am -
1 stop23h 56m
Deal found 9/16![Frontier logo]()
$320
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 11/57:29 pm -
2 stops18h 34m
Thu 11/124:33 pm -
2 stops17h 15m
Deal found 9/14![American Airlines logo]()
$326
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/1210:15 am -
1 stop26h 28m
Thu 11/193:55 am -
1 stop15h 31m
Deal found 9/16![Frontier logo]()
$334
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:15 am -
1 stop27h 21m
Sat 10/246:42 pm -
1 stop15h 38m
Deal found 9/12![Frontier logo]()
$338
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/317:19 pm -
2 stops16h 43m
Fri 11/61:02 pm -
1 stop11h 54m
Deal found 9/14![American Airlines logo]()
$357
This Priceline deal was found by Cheapflights users on 9/13. 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 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 9/13![Frontier logo]()
$362
This FlightHub deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1510:15 am -
1 stop14h 35m
Thu 11/193:55 am -
1 stop15h 31m
Deal found 9/16![Frontier logo]()
$365
This Frontier deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Fri 12/115:33 pm -
1 stop7h 09m
Mon 12/148:00 am -
1 stop10h 38m
Deal found 9/16![Frontier logo]()
$368
This Priceline deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/1010:15 am -
1 stop22h 00m
Mon 11/167:23 am -
1 stop27h 53m
Deal found 9/16![Frontier logo]()
$374
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 17, 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 17, 2026.
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 12/125:00 am -
1 stop7h 31m
Fri 12/183:00 pm -
1 stop10h 11m
Deal found 9/17![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2110:25 am -
1 stop11h 25m
Sat 1/237:30 am -
1 stop9h 24m
Deal found 9/15![Delta logo]()
$386
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:05 pm -
2 stops9h 50m
Sat 10/316:50 am -
2 stops9h 35m
Deal found 9/12![Southwest logo]()
$386
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 stops15h 51m
Deal found 9/15![American Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Thu 1/286:00 am -
1 stop8h 20m
Wed 2/33:00 pm -
1 stop10h 11m
Deal found 9/17![United Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 9/13. 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.
Tue 2/235:35 am -
1 stop8h 15m
Thu 2/2510:40 am -
1 stop13h 05m
Deal found 9/13![Southwest logo]()
$386
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 1/297:10 am -
1 stop7h 10m
Wed 2/33:00 pm -
1 stop10h 11m
Deal found 9/17![United Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Fri 1/2912:20 pm -
1 stop6h 40m
Sat 2/66:15 am -
1 stop7h 00m
Deal found 9/15![Delta logo]()
$440
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:15 pm -
2 stops8h 35m
Tue 12/157:40 am -
2 stops10h 20m
Deal found 9/15![Southwest logo]()
$415
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 1/175:06 pm -
2 stops17h 39m
Sun 1/243:52 pm -
2 stops17h 31m
Deal found 9/15![American Airlines logo]()
$463
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 Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/237:00 am -
1 stop7h 15m
Tue 3/21:50 pm -
1 stop11h 59m
Deal found 9/16![Delta logo]()
$482
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 9/13. 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.
Thu 10/85:00 am -
1 stop10h 45m
Thu 10/1512:35 pm -
2 stops11h 00m
Deal found 9/13![Southwest logo]()
$450
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 1/225:00 am -
2 stops15h 39m
Tue 1/263:51 pm -
1 stop9h 23m
Deal found 9/13![American Airlines logo]()
$518
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 1/251:30 pm -
2 stops23h 25m
Tue 2/93:25 pm -
2 stops18h 20m
Deal found 9/17![Delta logo]()
$495
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/286:47 am -
1 stop6h 01m
Wed 11/42:54 pm -
1 stop6h 56m
Deal found 9/13![United Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 3/67:05 pm -
1 stop12h 45m
Sat 3/139:40 pm -
1 stop12h 00m
Deal found 9/13![Southwest logo]()
$464
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/246:27 pm -
1 stop17h 03m
Fri 10/3012:25 pm -
1 stop11h 32m
Deal found 9/16![American Airlines logo]()
$519
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:29 pm -
2 stops16h 38m
Thu 11/124:10 pm -
2 stops17h 38m
Deal found 9/17![American Airlines logo]()
$521
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/215:55 am -
1 stop8h 20m
Mon 3/13:10 pm -
1 stop7h 58m
Deal found 9/16![Delta logo]()
$531
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 2/247:00 am -
1 stop5h 46m
Mon 3/12:48 pm -
1 stop18h 18m
Deal found 9/13![United Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/317:00 pm -
2 stops17h 45m
Thu 2/42:40 pm -
1 stop7h 10m
Deal found 9/16![Southwest logo]()
$494
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/245:55 am -
1 stop8h 20m
Mon 3/13:10 pm -
1 stop7h 58m
Deal found 9/16![Delta logo]()
$531
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/207:19 pm -
2 stops19h 04m
Sun 2/285:17 pm -
2 stops20h 18m
Deal found 9/17![American Airlines logo]()
$538
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/97:40 pm -
2 stops15h 35m
Fri 11/131:10 pm -
2 stops10h 05m
Deal found 9/16![Southwest logo]()
$514
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/2012:05 pm -
2 stops10h 45m
Wed 10/217:00 am -
1 stop11h 19m
Deal found 9/16![United Airlines logo]()
$471
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Tue 12/17:33 pm -
2 stops18h 05m
Tue 12/83:15 pm -
2 stops18h 33m
Deal found 9/13![American Airlines logo]()
$541
This Delta deal was found by Cheapflights users on 9/13. 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.
Tue 2/235:55 am -
1 stop7h 30m
Tue 3/22:10 pm -
1 stop7h 58m
Deal found 9/13![Delta logo]()
$543
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/3110:48 am -
2 stops9h 34m
Sat 11/78:25 am -
1 stop8h 33m
Deal found 9/13![United Airlines logo]()
$476
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated September 17, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/810:15 am -
1 stop11h 50m
Wed 10/146:42 pm -
1 stop15h 38m
Deal found 9/17![Frontier logo]()
$284
This Priceline deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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
Sat 10/103:00 am -
1 stop7h 20m
Deal found 9/16![Frontier logo]()
$308
This Priceline deal was found by Cheapflights users on 9/13. 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 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 9/13![Frontier logo]()
$362
This FlightHub deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:15 am -
1 stop14h 38m
Sat 10/173:00 am -
1 stop7h 20m
Deal found 9/17![Frontier logo]()
$375
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop14h 38m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 9/15![Frontier logo]()
$311
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/1711:45 am -
1 stop6h 20m
Mon 10/198:50 pm -
1 stop13h 05m
Deal found 9/16![Southwest logo]()
$386
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:15 am -
1 stop27h 21m
Sat 10/246:42 pm -
1 stop15h 38m
Deal found 9/12![Frontier logo]()
$338
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:02 pm -
2 stops19h 53m
Thu 10/291:48 pm -
2 stops21h 26m
Deal found 9/15![American Airlines logo]()
$326
This FlightHub deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop14h 35m
Mon 11/211:20 am -
1 stop23h 56m
Deal found 9/16![Frontier logo]()
$320
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/307:14 am -
1 stop8h 58m
Fri 11/61:21 pm -
1 stop9h 35m
Deal found 9/17![American Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/317:19 pm -
2 stops16h 43m
Fri 11/61:02 pm -
1 stop11h 54m
Deal found 9/14![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/315:47 pm -
1 stop23h 22m
Sat 11/71:21 pm -
1 stop9h 39m
Deal found 9/16![American Airlines logo]()
$389
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 17, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 1/303:17 pm -
2 stops20h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$152
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia 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 9/13![Frontier logo]()
$154
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 1/127:41 pm -
2 stops17h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$158
This Orbitz deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:15 am -
1 stop26h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$160
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 1/237:41 pm -
1 stop17h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$161
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 9/16![American Airlines logo]()
$167
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/36:47 pm -
2 stops18h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$182
This deal was found by Cheapflights users on 9/13. 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.
Fri 12/115:33 pm -
1 stop7h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$184
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/46:43 pm -
2 stops18h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$188
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:45 am -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$193
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/35:43 pm -
1 stop22h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$196
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/215:10 pm -
2 stops15h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$198
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 17, 2026.
Round-trip from | $284 (Cheapflightsfares) |
|---|---|
One-way from | $152 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $366 |
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 17, 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
3:17 pm-12:26 pm
2 stops20h 09m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$152
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Tue 1/12
7:41 pm-2:17 pm
2 stops17h 36m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
MilwaukeeSaint Thomas Island
MKE Milwaukee-Mitchell - STT Saint Thomas Island Cyril E King
MKESTT
Milwaukee-Mitchell
Wed 12/23
5:00 am-2:31 pm
1 stop7h 31m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
MilwaukeeSaint Thomas Island
MKE Milwaukee-Mitchell - STT Saint Thomas Island Cyril E King
MKESTT
Milwaukee-Mitchell
Fri 1/22
6:00 am-4:20 pm
1 stop8h 20m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
MilwaukeeSaint Thomas Island
MKE Milwaukee-Mitchell - STT Saint Thomas Island Cyril E King
MKESTT
Milwaukee-Mitchell
Fri 1/22
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
$167
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 10/5
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
Sat 11/7
10:50 am-8:30 pm
1 stop7h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 10/12
8:05 pm-9:10 am
1 stop12h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
Quickest round-trip
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 1/11
5:55 am-2:31 pm
1 stop6h 36m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 11/7
10:48 am-12:36 am
2 stops11h 48m
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-MBJ
MKE-SJU
MKE-STT
MKE-GCM
MKE-STX
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-MBJ
MKE-SJU
MKE-STT
MKE-GCM
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 17, 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
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
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 17, 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$356 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$224 | Average$606 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$617 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$703 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$320 | Average$725 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$492 | Average$580 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$547 | Average$853 | FlexibilityNo cancel fee | On-time83% |