$119+ Cheap flights from Milwaukee (MKE) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Oct 2 — Oct 91
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 2, 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 2, 2026.
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/1712:49 pm -
1 stop9h 08m
Tue 10/276:30 am -
2 stops14h 57m
Deal found 9/2![American Airlines logo]()
$238
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/277:19 pm -
2 stops18h 36m
Sat 10/311:48 pm -
2 stops23h 20m
Deal found 9/1![American Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/166:27 pm -
2 stops14h 19m
Sat 10/173:51 pm -
1 stop9h 06m
Deal found 9/2![American Airlines logo]()
$303
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:27 pm -
2 stops14h 19m
Wed 10/1410:36 am -
2 stops10h 22m
Deal found 9/2![American Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/2910:15 am -
1 stop30h 06m
Mon 11/211:20 am -
1 stop9h 48m
Deal found 8/29![Frontier logo]()
$311
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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
Fri 10/162:53 pm -
1 stop18h 14m
Deal found 9/2![American Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/76:02 pm -
2 stops16h 29m
Sat 10/106:30 am -
2 stops18h 04m
Deal found 9/2![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 stops17h 21m
Mon 10/262:53 pm -
1 stop18h 14m
Deal found 9/2![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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
Fri 10/912:21 pm -
2 stops12h 13m
Deal found 9/2![American Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/2910:15 am -
2 stops13h 44m
Wed 11/47:23 am -
1 stop27h 53m
Deal found 8/29![Frontier logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/2910:15 am -
1 stop30h 06m
Thu 11/53:55 am -
1 stop17h 13m
Deal found 8/29![Frontier logo]()
$329
This Priceline deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/1710:10 am -
1 stop27h 08m
Sat 9/269:50 pm -
1 stop12h 32m
Deal found 8/30![Frontier logo]()
$332
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 2, 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 2, 2026.
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/287:45 am -
2 stops11h 50m
Tue 11/37:40 am -
2 stops10h 20m
Deal found 8/30![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/57:05 am -
1 stop8h 44m
Fri 10/307:15 am -
1 stop11h 25m
Deal found 8/31![Delta logo]()
$366
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/147:17 am -
1 stop11h 56m
Tue 11/2411:31 am -
1 stop14h 23m
Deal found 8/28![American Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 11/76:47 am -
2 stops8h 32m
Sat 11/146:00 pm -
2 stops17h 13m
Deal found 9/2![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:55 pm -
1 stop9h 00m
Sat 10/107:50 am -
1 stop9h 35m
Deal found 8/28![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/128:05 pm -
1 stop12h 05m
Fri 10/166:30 am -
1 stop12h 20m
Deal found 8/30![Southwest logo]()
$366
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 1/97:19 pm -
1 stop17h 59m
Thu 1/212:52 pm -
2 stops10h 30m
Deal found 8/28![American Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/66:47 am -
1 stop6h 01m
Mon 11/163:20 pm -
2 stops18h 16m
Deal found 8/28![United Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 stops17h 59m
Mon 11/166:09 pm -
2 stops17h 59m
Deal found 8/28![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/1![Delta logo]()
$463
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/2210:00 am -
2 stops11h 05m
Sat 9/265:55 am -
1 stop7h 15m
Deal found 9/1![Southwest logo]()
$386
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/315:00 am -
1 stop7h 31m
Mon 11/23:00 pm -
1 stop9h 50m
Deal found 9/2![United Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 12/55:04 am -
1 stop8h 37m
Sat 12/128:15 am -
2 stops15h 51m
Deal found 9/2![American Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 20m
Wed 11/2510:30 pm -
1 stop14h 05m
Deal found 8/28![Southwest logo]()
$395
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 2/237:00 am -
2 stops8h 00m
Tue 3/25:06 pm -
2 stops21h 37m
Deal found 9/1![United Airlines logo]()
$468
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:20 pm -
1 stop13h 10m
Tue 12/157:40 am -
1 stop9h 50m
Deal found 8/31![Southwest logo]()
$395
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 1/255:55 am -
1 stop5h 55m
Sat 1/3012:40 pm -
1 stop9h 53m
Deal found 8/31![Delta logo]()
$553
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 11/46:47 am -
1 stop6h 01m
Tue 11/102:54 pm -
1 stop6h 58m
Deal found 9/2![United Airlines logo]()
$475
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 2/206:08 pm -
2 stops20h 15m
Sun 2/285:17 pm -
2 stops19h 29m
Deal found 8/31![American Airlines logo]()
$498
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 stop7h 24m
Sat 10/311:15 pm -
1 stop5h 10m
Deal found 8/28![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/216:25 am -
2 stops10h 20m
Sat 1/306:55 am -
2 stops11h 10m
Deal found 9/2![Southwest logo]()
$456
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:05 am -
1 stop5h 48m
Tue 9/291:16 pm -
1 stop8h 38m
Deal found 8/29![Delta logo]()
$556
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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
Thu 10/292:01 pm -
1 stop8h 14m
Deal found 8/28![United Airlines logo]()
$512
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 2/206:08 pm -
2 stops18h 09m
Sat 2/275:17 pm -
2 stops16h 50m
Deal found 8/31![American Airlines logo]()
$533
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 stop7h 10m
Tue 3/22:40 pm -
1 stop7h 10m
Deal found 9/1![Southwest logo]()
$463
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 1/36:40 am -
1 stop6h 05m
Wed 1/132:25 pm -
2 stops18h 42m
Deal found 9/1![United Airlines logo]()
$512
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 2/205:55 am -
1 stop6h 40m
Sat 2/273:35 pm -
1 stop7h 33m
Deal found 9/1![Delta logo]()
$564
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 1/295:55 am -
1 stop6h 40m
Mon 2/13:35 pm -
1 stop7h 33m
Deal found 8/29![Delta logo]()
$564
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 1/93:42 pm -
2 stops12h 33m
Wed 1/208:05 am -
2 stops13h 05m
Deal found 8/28![United Airlines logo]()
$514
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 -
1 stop18h 13m
Thu 2/251:26 pm -
1 stop11h 22m
Deal found 9/1![American Airlines logo]()
$569
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated September 2, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/1710:10 am -
1 stop27h 08m
Sat 9/269:50 pm -
1 stop12h 32m
Deal found 8/30![Frontier logo]()
$332
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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
Fri 10/912:21 pm -
2 stops12h 13m
Deal found 9/2![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/76:02 pm -
2 stops16h 29m
Sat 10/106:30 am -
2 stops18h 04m
Deal found 9/2![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:27 pm -
2 stops14h 19m
Wed 10/1410:36 am -
2 stops10h 22m
Deal found 9/2![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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
Fri 10/162:53 pm -
1 stop18h 14m
Deal found 9/2![American Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/166:27 pm -
2 stops14h 19m
Sat 10/173:51 pm -
1 stop9h 06m
Deal found 9/2![American Airlines logo]()
$303
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/1712:49 pm -
1 stop9h 08m
Tue 10/276:30 am -
2 stops14h 57m
Deal found 9/2![American Airlines logo]()
$238
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 stops17h 21m
Mon 10/262:53 pm -
1 stop18h 14m
Deal found 9/2![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/277:19 pm -
2 stops18h 36m
Sat 10/311:48 pm -
2 stops23h 20m
Deal found 9/1![American Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/2910:15 am -
1 stop30h 06m
Mon 11/211:20 am -
1 stop9h 48m
Deal found 8/29![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/2910:15 am -
2 stops13h 44m
Wed 11/47:23 am -
1 stop27h 53m
Deal found 8/29![Frontier logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/2910:15 am -
1 stop30h 06m
Thu 11/53:55 am -
1 stop17h 13m
Deal found 8/29![Frontier logo]()
$329
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 2, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:27 pm -
2 stops14h 19m
Deal found 9/2![American Airlines logo]()
$119
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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
Deal found 9/2![American Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 stops16h 04m
Deal found 9/2![American Airlines logo]()
$125
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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.
Thu 10/1510:15 am -
1 stop11h 50m
Deal found 9/1![Frontier logo]()
$134
This Trip.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:15 am -
1 stop22h 03m
Deal found 8/31![Frontier logo]()
$142
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 1/105:04 am -
1 stop8h 10m
Deal found 9/2![American Airlines logo]()
$149
This Orbitz deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Sun 10/1810:15 am -
1 stop22h 03m
Deal found 8/31![Frontier logo]()
$180
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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
Deal found 9/2![American Airlines logo]()
$182
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/135:10 pm -
2 stops17h 21m
Deal found 8/31![American Airlines logo]()
$186
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 12/286:40 pm -
1 stop16h 05m
Deal found 8/30![Delta logo]()
$225
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 2/15:00 am -
1 stop7h 48m
Deal found 9/1![United Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/157:19 pm -
2 stops17h 49m
Deal found 8/28![American Airlines logo]()
$247
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 2, 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 | $729 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 2, 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
Wed 10/28
7:45 am-8:35 pm
2 stops11h 50m
San Juan Luis Munoz Marin Intl
Tue 11/3
7:40 am-4:00 pm
2 stops10h 20m
$366
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 10/5
7:05 am-4:49 pm
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Fri 10/30
7:15 am-5:40 pm
1 stop11h 25m
$366
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 11/14
7:17 am-9:13 pm
1 stop11h 56m
San Juan Luis Munoz Marin Intl
Tue 11/24
11:31 am-11:54 pm
1 stop14h 23m
$366
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Fri 9/25
1:55 pm-11:55 pm
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Sat 10/10
7:50 am-4:25 pm
1 stop9h 35m
$366
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
Fri 10/16
6:30 am-5:50 pm
1 stop12h 20m
$366
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Tue 9/22
10:00 am-10:05 pm
2 stops11h 05m
San Juan Luis Munoz Marin Intl
Sat 9/26
5:55 am-12:10 pm
1 stop7h 15m
$386
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 11/14
7:05 am-8:25 pm
2 stops11h 20m
San Juan Luis Munoz Marin Intl
Wed 11/25
10:30 pm-10:35 am
1 stop14h 05m
$395
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 12/10
7:20 pm-10:30 am
1 stop13h 10m
San Juan Luis Munoz Marin Intl
Tue 12/15
7:40 am-3:30 pm
1 stop9h 50m
$395
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 1/9
7:19 pm-3:18 pm
1 stop17h 59m
San Juan Luis Munoz Marin Intl
Thu 1/21
2:52 pm-11:22 pm
2 stops10h 30m
$406
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 11/7
6:47 am-4:19 pm
2 stops8h 32m
Montego Bay Sangster Intl
Sat 11/14
6:00 pm-10:13 am
2 stops17h 13m
$417
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-PLS
MKE-STT
MKE-GCM
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-PLS
MKE-STT
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $493). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $735). 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 2, 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.
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
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 2, 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$341 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$215 | Average$604 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$238 | Average$615 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$699 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$319 | Average$745 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$492 | Average$580 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |