$162+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Sep 8 — Sep 151
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Milwaukee to CaribbeanExplore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 9, 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 August 9, 2026.
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:05 pm -
1 stop7h 00m
Wed 9/96:00 am -
1 stop7h 00m
Deal found 8/7![Southwest logo]()
$341
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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
Fri 11/62:05 am -
2 stops11h 23m
Deal found 8/5![United Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:10 pm -
2 stops17h 21m
Sat 10/246:30 am -
2 stops11h 27m
Deal found 8/8![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:27 pm -
2 stops16h 04m
Fri 10/306:00 am -
1 stop16h 52m
Deal found 8/5![American Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:11 pm -
2 stops16h 49m
Sun 9/206:00 am -
2 stops12h 52m
Deal found 8/7![American Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 11/128:03 pm -
1 stop16h 13m
Mon 11/167:05 am -
1 stop14h 03m
Deal found 8/4![Frontier logo]()
$362
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:58 pm -
1 stop8h 26m
Wed 9/96:00 am -
2 stops11h 41m
Deal found 8/7![American Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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.
Sun 9/2010:10 am -
1 stop14h 42m
Sat 10/310:42 am -
1 stop23h 40m
Deal found 8/4![Frontier logo]()
$369
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/75:00 am -
2 stops8h 51m
Sat 9/196:00 am -
2 stops12h 23m
Deal found 8/4![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:30 am -
1 stop10h 05m
Fri 11/136:00 pm -
1 stop16h 11m
Deal found 8/7![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 11/1412:28 pm -
2 stops20h 47m
Thu 11/1911:05 am -
1 stop13h 46m
Deal found 8/4![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 -
2 stops19h 10m
Tue 10/131:34 pm -
2 stops20h 40m
Deal found 8/4![American Airlines logo]()
$412
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 August 9, 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 August 9, 2026.
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/1910:30 am -
2 stops12h 20m
Fri 10/21:00 am -
2 stops10h 07m
Deal found 8/4![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/210:30 am -
1 stop9h 35m
Sun 9/66:30 am -
1 stop8h 25m
Deal found 8/5![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 11/178:10 am -
1 stop7h 10m
Thu 12/33:35 pm -
1 stop7h 28m
Deal found 8/5![Delta logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:14 pm -
2 stops17h 36m
Mon 9/286:00 am -
2 stops11h 41m
Deal found 8/8![American Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:55 pm -
1 stop7h 20m
Mon 9/286:30 am -
2 stops9h 55m
Deal found 8/8![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 stop7h 15m
Fri 10/305:59 pm -
1 stop6h 54m
Deal found 8/5![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/306:00 am -
2 stops9h 24m
Sat 2/63:20 pm -
1 stop8h 26m
Deal found 8/7![United Airlines logo]()
$393
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 1/106:30 am -
1 stop7h 02m
Thu 1/213:36 pm -
1 stop8h 36m
Deal found 8/4![American Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/156:47 pm -
2 stops16h 56m
Tue 9/2212:52 pm -
2 stops21h 08m
Deal found 8/5![United Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/155:30 am -
1 stop6h 10m
Sun 9/202:05 pm -
1 stop8h 25m
Deal found 8/4![Delta logo]()
$423
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 10/246:10 am -
1 stop7h 05m
Wed 10/283:02 pm -
2 stops20h 12m
Deal found 8/5![American Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:00 am -
1 stop5h 46m
Thu 12/103:36 pm -
1 stop8h 51m
Deal found 8/7![United Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 11/163:40 pm -
2 stops19h 35m
Sat 11/213:00 pm -
2 stops10h 15m
Deal found 8/5![Southwest logo]()
$494
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 1/195:55 am -
1 stop7h 10m
Thu 1/284:15 pm -
1 stop9h 34m
Deal found 8/5![Delta logo]()
$450
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 12/55:00 am -
2 stops10h 00m
Sat 12/122:23 pm -
1 stop9h 16m
Deal found 8/5![United Airlines logo]()
$423
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:00 am -
1 stop5h 23m
Sat 10/242:23 pm -
1 stop10h 34m
Deal found 8/7![American Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 1/187:00 am -
1 stop7h 15m
Wed 1/274:15 pm -
1 stop9h 34m
Deal found 8/5![Delta logo]()
$450
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 2/44:20 pm -
2 stops20h 15m
Fri 2/124:15 pm -
2 stops18h 55m
Deal found 8/6![Southwest logo]()
$504
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:48 am -
2 stops9h 34m
Wed 10/287:05 am -
2 stops11h 33m
Deal found 8/8![United Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:01 am -
1 stop9h 15m
Tue 10/135:13 pm -
2 stops17h 59m
Deal found 8/8![American Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 12/15:30 am -
1 stop10h 05m
Wed 12/96:00 pm -
1 stop6h 54m
Deal found 8/4![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 1/125:35 am -
1 stop7h 00m
Sat 1/162:30 pm -
1 stop9h 25m
Deal found 8/5![Southwest logo]()
$571
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/55:00 am -
2 stops11h 39m
Thu 9/1010:32 am -
2 stops12h 22m
Deal found 8/6![American Airlines logo]()
$532
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 11/166:18 pm -
2 stops16h 31m
Sat 11/214:00 pm -
1 stop5h 50m
Deal found 8/5![United Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:03 am -
1 stop5h 54m
Thu 9/101:16 pm -
1 stop9h 14m
Deal found 8/7![Delta logo]()
$524
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:24 pm -
2 stops19h 07m
Tue 11/173:26 pm -
2 stops21h 42m
Deal found 8/7![American Airlines logo]()
$541
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 10/276:47 am -
1 stop6h 01m
Thu 10/292:20 pm -
1 stop8h 30m
Deal found 8/6![United Airlines logo]()
$492
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/235:00 am -
1 stop7h 50m
Sat 1/302:30 pm -
1 stop9h 25m
Deal found 8/5![Southwest logo]()
$598
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am -
1 stop5h 45m
Sat 12/123:10 pm -
1 stop8h 08m
Deal found 8/8![Delta logo]()
$541
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/226:35 am -
1 stop6h 43m
Tue 8/253:03 pm -
2 stops20h 59m
Deal found 8/4![American Airlines logo]()
$546
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated August 9, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:10 pm -
1 stop6h 42m
Mon 8/313:10 am -
1 stop9h 03m
Deal found 8/8![Frontier logo]()
$376
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/275:00 am -
1 stop17h 15m
Tue 9/82:33 pm -
1 stop7h 33m
Deal found 8/4![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/2812:58 pm -
1 stop8h 26m
Thu 9/312:55 am -
1 stop12h 52m
Deal found 8/5![American Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/26:00 am -
2 stops11h 33m
Sun 9/610:33 am -
2 stops11h 33m
Deal found 8/5![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/75:00 am -
2 stops8h 51m
Sat 9/196:00 am -
2 stops12h 23m
Deal found 8/4![American Airlines logo]()
$371
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:05 pm -
1 stop7h 00m
Wed 9/96:00 am -
1 stop7h 00m
Deal found 8/7![Southwest logo]()
$341
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:58 pm -
1 stop8h 26m
Wed 9/96:00 am -
2 stops11h 41m
Deal found 8/7![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/115:53 pm -
2 stops16h 07m
Tue 9/1511:51 am -
2 stops11h 03m
Deal found 8/4![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/157:05 pm -
1 stop16h 38m
Tue 9/2212:52 pm -
1 stop10h 45m
Deal found 8/5![United Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:11 pm -
2 stops16h 49m
Sun 9/206:00 am -
2 stops12h 52m
Deal found 8/7![American Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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.
Sun 9/2010:10 am -
1 stop14h 42m
Sat 10/310:42 am -
1 stop23h 40m
Deal found 8/4![Frontier logo]()
$369
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:25 am -
2 stops9h 30m
Sun 9/275:00 am -
1 stop7h 10m
Deal found 8/7![Southwest logo]()
$374
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 August 9, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This Trip.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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.
Sun 10/188:10 pm -
1 stop28h 43m
Deal found 8/6![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/812:10 pm -
1 stop28h 33m
Deal found 8/6![Frontier logo]()
$164
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 1/306:40 am -
1 stop7h 36m
Deal found 8/4![American Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/212:55 pm -
1 stop6h 24m
Deal found 8/7![Delta logo]()
$173
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/256:20 am -
2 stops11h 13m
Deal found 8/4![American Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/26:00 am -
1 stop16h 15m
Deal found 8/4![American Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:27 pm -
2 stops16h 04m
Deal found 8/7![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:48 pm -
2 stops17h 36m
Deal found 8/7![American Airlines logo]()
$182
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:10 pm -
1 stop13h 05m
Deal found 8/7![Frontier logo]()
$198
This FlightHub deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/2410:10 am -
1 stop14h 42m
Deal found 8/4![Frontier logo]()
$200
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:30 pm -
1 stop9h 25m
Deal found 8/8![Southwest logo]()
$201
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:21 am -
2 stops25h 21m
Deal found 8/7![American Airlines logo]()
$213
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 August 9, 2026.
Round-trip from | $335 (Kiwi.com) |
|---|---|
One-way from | $162 (Trip.com) |
Popular in | December |
Cheapest in | October |
Average price | $408 |
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 2,558,603 searches. Data last updated August 9, 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
Sat 9/19
10:30 am-11:50 pm
2 stops12h 20m
San Juan Luis Munoz Marin Intl
Fri 10/2
1:00 am-10:07 am
2 stops10h 07m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Wed 9/2
10:30 am-9:05 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Sun 9/6
6:30 am-1:55 pm
1 stop8h 25m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Tue 11/17
8:10 am-5:20 pm
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Thu 12/3
3:35 pm-9:03 pm
1 stop7h 28m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 9/24
8:14 pm-2:50 pm
2 stops17h 36m
San Juan Luis Munoz Marin Intl
Mon 9/28
6:00 am-4:41 pm
2 stops11h 41m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 9/24
1:55 pm-10:15 pm
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Mon 9/28
6:30 am-3:25 pm
2 stops9h 55m
$346
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 10/5
5:30 am-1:45 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Fri 10/30
5:59 pm-11:53 pm
1 stop6h 54m
$346
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/30
6:00 am-4:24 pm
2 stops9h 24m
Montego Bay Sangster Intl
Sat 2/6
3:20 pm-10:46 pm
1 stop8h 26m
$393
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Tue 9/15
6:47 pm-11:43 am
2 stops16h 56m
Montego Bay Sangster Intl
Tue 9/22
12:52 pm-10:00 am
2 stops21h 08m
$397
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Wed 12/2
7:00 am-1:46 pm
1 stop5h 46m
Montego Bay Sangster Intl
Thu 12/10
3:36 pm-11:27 pm
1 stop8h 51m
$413
MilwaukeeProvidenciales
MKE Milwaukee-Mitchell - PLS Providenciales
MKEPLS
Milwaukee-Mitchell
Sun 1/10
6:30 am-2:32 pm
1 stop7h 02m
Providenciales
Thu 1/21
3:36 pm-11:12 pm
1 stop8h 36m
$423
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-NAS
MKE-STT
MKE-PUJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to Caribbean
MKE-0CB
MKE-SJU
MKE-MBJ
MKE-NAS
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 $471). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $725). 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 August 9, 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.
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 August 9, 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 2,558,603 searches. Data last updated August 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$143 | Average$594 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$572 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$637 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$726 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$465 | Average$567 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$547 | Average$853 | FlexibilityNo cancel fee | On-time83% |