$142+ Cheap flights from Milwaukee (MKE) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Oct 23 — Oct 301
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 23, 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 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/2910:15 am -
1 stop27h 27m
Mon 11/27:23 am -
1 stop27h 53m
Deal found 9/22![Frontier logo]()
$283
This Priceline deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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
Sat 11/143:55 am -
1 stop7h 21m
Deal found 9/22![Frontier logo]()
$318
This FlightHub deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/810:15 am -
1 stop14h 35m
Wed 11/113:55 am -
1 stop7h 21m
Deal found 9/21![Frontier logo]()
$321
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 stops16h 22m
Thu 10/291:21 pm -
2 stops19h 46m
Deal found 9/18![American Airlines logo]()
$326
This CheapOair deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:15 am -
1 stop22h 03m
Sat 10/243:00 am -
1 stop7h 20m
Deal found 9/20![Frontier logo]()
$339
This Cheapflightsfares deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sun 10/1110:15 am -
1 stop14h 38m
Sat 10/173:00 am -
1 stop7h 20m
Deal found 9/20![Frontier logo]()
$345
This Frontier deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/810:15 am -
1 stop11h 50m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 9/20![Frontier logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:15 am -
1 stop30h 05m
Tue 11/33:59 pm -
2 stops43h 17m
Deal found 9/21![Frontier logo]()
$350
This Trip.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Thu 10/810:15 am -
1 stop14h 38m
Sat 10/103:00 am -
1 stop7h 20m
Deal found 9/21![Frontier logo]()
$357
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 12/66:00 am -
1 stop6h 48m
Thu 12/102:54 pm -
1 stop9h 01m
Deal found 9/21![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 12/65:08 pm -
2 stops16h 07m
Thu 12/103:56 pm -
1 stop16h 52m
Deal found 9/20![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/305:47 pm -
1 stop22h 25m
Fri 11/62:12 pm -
1 stop9h 43m
Deal found 9/18![American Airlines logo]()
$420
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 23, 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 23, 2026.
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 -
2 stops16h 26m
Sat 12/55:25 pm -
2 stops19h 43m
Deal found 9/18![American Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/247:03 am -
1 stop8h 45m
Fri 10/305:59 pm -
1 stop6h 54m
Deal found 9/21![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/105:30 am -
1 stop8h 45m
Wed 10/145:50 am -
1 stop7h 05m
Deal found 9/18![Southwest logo]()
$386
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 12/66:00 am -
1 stop6h 48m
Thu 12/102:54 pm -
1 stop9h 01m
Deal found 9/20![United Airlines logo]()
$412
This Mytrip deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:15 am -
2 stops22h 40m
Mon 11/97:26 pm -
1 stop15h 50m
Deal found 9/22![Frontier logo]()
$436
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/145:04 am -
2 stops14h 09m
Thu 11/198:25 am -
2 stops11h 20m
Deal found 9/23![American Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/2910:25 am -
1 stop13h 00m
Mon 11/24:00 pm -
2 stops9h 30m
Deal found 9/22![Southwest logo]()
$386
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 12/55:53 pm -
2 stops17h 20m
Wed 12/92:54 pm -
1 stop9h 01m
Deal found 9/20![United Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 1/226:40 pm -
1 stop15h 30m
Wed 1/274:50 pm -
1 stop7h 59m
Deal found 9/19![Delta logo]()
$413
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:47 pm -
2 stops18h 52m
Fri 10/3012:25 pm -
1 stop10h 39m
Deal found 9/20![United Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 1/264:14 pm -
2 stops19h 12m
Tue 2/96:05 pm -
2 stops18h 59m
Deal found 9/22![American Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 1/295:00 pm -
2 stops19h 55m
Fri 2/512:35 pm -
1 stop12h 14m
Deal found 9/19![Delta logo]()
$418
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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
Mon 11/94:00 pm -
2 stops9h 35m
Deal found 9/22![Southwest logo]()
$480
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/212:30 pm -
1 stop7h 40m
Sun 10/253:05 pm -
1 stop9h 50m
Deal found 9/21![Southwest logo]()
$480
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 am -
1 stop10h 19m
Fri 10/305:59 pm -
1 stop6h 54m
Deal found 9/21![Delta logo]()
$481
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/205:30 am -
2 stops14h 08m
Tue 10/201:00 am -
2 stops10h 07m
Deal found 9/19![United Airlines logo]()
$481
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/32:55 pm -
2 stops19h 21m
Tue 11/102:01 pm -
1 stop11h 05m
Deal found 9/18![American Airlines logo]()
$490
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/35:55 am -
1 stop5h 40m
Tue 11/101:30 pm -
1 stop8h 35m
Deal found 9/19![Southwest logo]()
$493
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 9/22![Delta logo]()
$497
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 1/316:39 pm -
2 stops17h 38m
Thu 2/42:23 pm -
2 stops18h 44m
Deal found 9/22![United Airlines logo]()
$502
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 -
2 stops13h 59m
Sun 1/243:52 pm -
2 stops17h 31m
Deal found 9/18![American Airlines logo]()
$531
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 9/22![Southwest logo]()
$502
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 1/66:45 pm -
1 stop16h 28m
Mon 1/112:54 pm -
1 stop18h 13m
Deal found 9/19![United Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 2/11:30 pm -
2 stops23h 25m
Sat 2/63:40 pm -
1 stop6h 28m
Deal found 9/19![Delta logo]()
$513
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 55m
Deal found 9/19![American Airlines logo]()
$538
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/166:38 pm -
1 stop16h 55m
Sat 10/241:35 pm -
1 stop11h 02m
Deal found 9/22![United Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 1/246:40 pm -
1 stop18h 00m
Fri 1/291:40 pm -
1 stop9h 28m
Deal found 9/18![Delta logo]()
$526
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 12/124:20 pm -
1 stop16h 28m
Deal found 9/21![American Airlines logo]()
$539
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 1/265:35 am -
1 stop6h 25m
Tue 2/21:55 pm -
2 stops7h 15m
Deal found 9/20![Southwest logo]()
$540
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/269:18 am -
2 stops27h 56m
Thu 10/2912:25 pm -
2 stops20h 10m
Deal found 9/18![United Airlines logo]()
$527
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated September 23, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:10 am -
1 stop22h 25m
Sat 10/173:00 am -
1 stop7h 20m
Deal found 9/20![Frontier logo]()
$363
This Justfly.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:10 am -
1 stop22h 25m
Mon 10/197:20 am -
1 stop27h 00m
Deal found 9/20![Frontier logo]()
$372
This Frontier deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/810:15 am -
1 stop11h 50m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 9/20![Frontier logo]()
$349
This Trip.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Thu 10/810:15 am -
1 stop14h 38m
Sat 10/103:00 am -
1 stop7h 20m
Deal found 9/21![Frontier logo]()
$357
This Cheapflightsfares deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates ” 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.
Sun 10/1110:15 am -
1 stop14h 38m
Sat 10/173:00 am -
1 stop7h 20m
Deal found 9/20![Frontier logo]()
$345
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/173:51 pm -
2 stops21h 39m
Sat 10/242:40 pm -
1 stop7h 57m
Deal found 9/19![United Airlines logo]()
$412
This CheapOair deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:15 am -
1 stop22h 03m
Sat 10/243:00 am -
1 stop7h 20m
Deal found 9/20![Frontier logo]()
$339
This Mytrip deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:15 am -
2 stops29h 11m
Tue 10/2712:59 am -
2 stops33h 17m
Deal found 9/19![Frontier logo]()
$365
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 stops16h 22m
Thu 10/291:21 pm -
2 stops19h 46m
Deal found 9/18![American Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:15 am -
1 stop30h 05m
Tue 11/33:59 pm -
2 stops43h 17m
Deal found 9/21![Frontier logo]()
$350
This Cheapflightsfares deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/2910:15 am -
1 stop27h 27m
Mon 11/27:23 am -
1 stop27h 53m
Deal found 9/22![Frontier logo]()
$283
This Priceline deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop14h 35m
Sat 10/313:55 am -
1 stop7h 21m
Deal found 9/20![Frontier logo]()
$288
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 23, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 9/22![Frontier logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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.
Sun 10/1810:15 am -
1 stop22h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:15 am -
2 stops29h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$174
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 9/18![American Airlines logo]()
$182
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/187:24 pm -
2 stops17h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$188
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/1610:25 am -
1 stop13h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$193
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/175:47 pm -
1 stop22h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![American Airlines logo]()
$196
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/216:03 am -
2 stops15h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![American Airlines logo]()
$198
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![American Airlines logo]()
$199
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/305:00 am -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![American Airlines logo]()
$201
This Cheapflightsfares deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$203
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 1/312:36 pm -
2 stops21h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$204
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 23, 2026.
Round-trip from | $283 (Cheapflightsfares) |
|---|---|
One-way from | $142 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $376 |
Good round-trip deal | $969 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 23, 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
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 10/19
5:30 am-3:27 pm
1 stop9h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 3/1
7:20 pm-12:07 pm
2 stops15h 47m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 10/17
6:47 pm-1:30 pm
2 stops18h 43m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 11/15
10:20 am-4:57 pm
1 stop5h 37m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 3/1
6:38 pm-12:24 pm
1 stop16h 46m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 2/28
7:00 am-1:46 pm
1 stop5h 46m
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
Fri 10/16
8:05 pm-9:40 am
1 stop12h 35m
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
Wed 12/9
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
$193
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 12/10
12:53 pm-11:13 pm
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Milwaukee with our price prediction graph.
MKE-SJU
MKE-MBJ
MKE-PLS
MKE-PUJ
MKE-NAS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to Caribbean
MKE-0CB
MKE-SJU
MKE-MBJ
MKE-PLS
MKE-PUJ
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 $481). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $731). 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 23, 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
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
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 23, 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$356 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$619 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$601 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$700 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$273 | Average$539 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$321 | Average$725 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$853 | FlexibilityNo cancel fee | On-time83% |