$163+ 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Aug 15 — Aug 221
Round-trip
1 adult, Economy
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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 July 16, 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 July 16, 2026.
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:21 am
MKE
- SJU
2 stops10h 34m
American Airlines
Fri 8/217:03 am
SJU
- MKE
1 stop11h 27m
American Airlines
Deal found 7/13![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:28 am
MKE
- SJU
1 stop16h 31m
American Airlines
Tue 8/182:33 pm
SJU
- MKE
1 stop9h 41m
American Airlines
Deal found 7/11![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:27 pm
MKE
- SJU
2 stops14h 19m
American Airlines
Fri 10/3012:13 pm
SJU
- MKE
2 stops12h 05m
American Airlines
Deal found 7/12![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:58 pm
MKE
- SJU
2 stops10h 01m
American Airlines
Sat 8/157:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Deal found 7/11![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:17 pm
MKE
- SJU
1 stop8h 58m
American Airlines
Tue 8/117:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Deal found 7/12![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:49 pm
MKE
- SJU
1 stop8h 10m
American Airlines
Mon 8/177:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Deal found 7/11![American Airlines logo]()
$338
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Fri 8/147:03 am
SJU
- MKE
1 stop11h 27m
American Airlines
Deal found 7/13![American Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:17 pm
MKE
- SJU
1 stop8h 37m
American Airlines
Fri 8/2812:55 am
SJU
- MKE
1 stop14h 17m
American Airlines
Deal found 7/15![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:28 am
MKE
- SJU
1 stop16h 31m
American Airlines
Sat 9/512:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/14![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:34 am
MKE
- SJU
2 stops10h 59m
American Airlines
Mon 9/1410:16 am
SJU
- MKE
2 stops12h 38m
American Airlines
Deal found 7/11![American Airlines logo]()
$358
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:14 pm
MKE
- MBJ
2 stops16h 39m
American Airlines
Tue 10/135:13 pm
MBJ
- MKE
2 stops18h 55m
American Airlines
Deal found 7/12![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:00 am
MKE
- MBJ
1 stop8h 22m
American Airlines
Fri 11/131:55 pm
MBJ
- MKE
1 stop25h 17m
American Airlines
Deal found 7/12![American Airlines logo]()
$380
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 July 16, 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 July 16, 2026.
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:00 am
MKE
- SJU
1 stop11h 05m
Southwest
Sun 9/206:00 am
SJU
- MKE
1 stop8h 35m
Southwest
Deal found 7/14![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:30 am
MKE
- SJU
1 stop7h 17m
Delta
Sun 9/202:59 pm
SJU
- MKE
1 stop7h 31m
Delta
Deal found 7/15![Delta logo]()
$361
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:00 am
MKE
- MBJ
1 stop8h 22m
American Airlines
Wed 11/1110:56 am
MBJ
- MKE
2 stops14h 03m
American Airlines
Deal found 7/15![American Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:15 am
MKE
- SJU
1 stop7h 29m
United Airlines
Tue 10/277:25 am
SJU
- MKE
1 stop7h 23m
United Airlines
Deal found 7/11![United Airlines logo]()
$416
This Priceline deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:36 am
MKE
- AUA
1 stop25h 59m
JetBlue
Tue 9/84:50 pm
AUA
- MKE
1 stop18h 45m
JetBlue
Deal found 7/13![JetBlue logo]()
$576
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Mon 8/316:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/11![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:11 am
MKE
- SJU
1 stop11h 08m
Delta
Tue 10/62:31 pm
SJU
- MKE
1 stop7h 31m
Delta
Deal found 7/14![Delta logo]()
$371
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Sun 9/135:30 am
SJU
- MKE
1 stop7h 40m
Southwest
Deal found 7/14![Southwest logo]()
$361
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:03 pm
MKE
- SJU
2 stops10h 33m
United Airlines
Sat 11/78:05 am
SJU
- MKE
2 stops11h 33m
United Airlines
Deal found 7/12![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:48 pm
MKE
- STT
2 stops17h 04m
American Airlines
Tue 12/82:49 pm
STT
- MKE
2 stops10h 41m
American Airlines
Deal found 7/11![American Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:30 am
MKE
- SJU
1 stop13h 25m
Southwest
Fri 8/1410:00 am
SJU
- MKE
1 stop7h 20m
Southwest
Deal found 7/15![Southwest logo]()
$361
This United Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:15 am
MKE
- SJU
1 stop7h 29m
United Airlines
Wed 10/211:00 am
SJU
- MKE
2 stops11h 30m
United Airlines
Deal found 7/11![United Airlines logo]()
$416
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:45 pm
MKE
- SJU
1 stop10h 20m
Southwest
Mon 11/96:35 am
SJU
- MKE
1 stop7h 30m
Southwest
Deal found 7/12![Southwest logo]()
$363
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:34 am
MKE
- MBJ
1 stop6h 10m
Delta
Sat 8/221:09 pm
MBJ
- MKE
1 stop7h 00m
Delta
Deal found 7/12![Delta logo]()
$442
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:02 pm
MKE
- STT
2 stops19h 53m
American Airlines
Thu 10/153:46 pm
STT
- MKE
2 stops20h 26m
American Airlines
Deal found 7/13![American Airlines logo]()
$450
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Sat 9/191:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 7/13![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:12 am
MKE
- MBJ
1 stop7h 43m
American Airlines
Tue 12/2211:27 am
MBJ
- MKE
1 stop13h 31m
American Airlines
Deal found 7/15![American Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Tue 9/291:00 am
SJU
- MKE
2 stops11h 30m
United Airlines
Deal found 7/11![United Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:34 am
MKE
- SXM
1 stop7h 19m
Delta
Fri 8/213:18 pm
SXM
- MKE
1 stop9h 35m
Delta
Deal found 7/11![Delta logo]()
$503
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:00 pm
MKE
- SXM
2 stops20h 39m
American Airlines
Fri 8/214:39 pm
SXM
- MKE
2 stops19h 23m
American Airlines
Deal found 7/11![American Airlines logo]()
$470
This Justfly.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:25 am
MKE
- AUA
1 stop27h 15m
JetBlue
Sat 9/194:30 pm
AUA
- MKE
1 stop19h 05m
JetBlue
Deal found 7/15![JetBlue logo]()
$659
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am
MKE
- MBJ
1 stop6h 46m
United Airlines
Sat 12/123:36 pm
MBJ
- MKE
1 stop8h 51m
United Airlines
Deal found 7/15![United Airlines logo]()
$452
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/85:55 am
MKE
- STT
1 stop8h 20m
Delta
Fri 1/151:50 pm
STT
- MKE
1 stop11h 59m
Delta
Deal found 7/11![Delta logo]()
$504
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:20 pm
MKE
- NAS
2 stops15h 55m
Southwest
Fri 9/181:10 pm
NAS
- MKE
1 stop8h 35m
Southwest
Deal found 7/13![Southwest logo]()
$474
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:53 pm
MKE
- STT
2 stops17h 58m
American Airlines
Sun 9/271:41 pm
STT
- MKE
2 stops24h 00m
American Airlines
Deal found 7/12![American Airlines logo]()
$491
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:34 am
MKE
- PLS
1 stop6h 06m
Delta
Sat 9/122:05 pm
PLS
- MKE
1 stop8h 25m
Delta
Deal found 7/12![Delta logo]()
$513
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:05 pm
MKE
- NAS
1 stop17h 28m
United Airlines
Fri 9/182:35 pm
NAS
- MKE
2 stops20h 25m
United Airlines
Deal found 7/13![United Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:19 pm
MKE
- STT
1 stop17h 21m
American Airlines
Sat 12/54:22 pm
STT
- MKE
1 stop9h 39m
American Airlines
Deal found 7/14![American Airlines logo]()
$495
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:40 am
MKE
- PLS
1 stop6h 05m
Delta
Tue 11/32:05 pm
PLS
- MKE
1 stop7h 57m
Delta
Deal found 7/11![Delta logo]()
$523
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:05 am
MKE
- NAS
1 stop5h 10m
Southwest
Sat 8/291:25 pm
NAS
- MKE
1 stop6h 55m
Southwest
Deal found 7/11![Southwest logo]()
$528
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 16, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 16, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:17 pm
MKE
- SJU
1 stop8h 58m
American Airlines
Tue 8/117:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Deal found 7/12![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/52:49 pm
MKE
- SJU
1 stop8h 10m
American Airlines
Wed 8/127:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Deal found 7/15![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:58 pm
MKE
- SJU
1 stop8h 26m
American Airlines
Sun 8/97:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Deal found 7/12![American Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:30 am
MKE
- SJU
1 stop13h 25m
Southwest
Fri 8/1410:00 am
SJU
- MKE
1 stop7h 20m
Southwest
Deal found 7/15![Southwest logo]()
$361
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:28 am
MKE
- SJU
1 stop16h 31m
American Airlines
Tue 8/182:33 pm
SJU
- MKE
1 stop9h 41m
American Airlines
Deal found 7/11![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:49 pm
MKE
- SJU
1 stop8h 10m
American Airlines
Mon 8/177:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Deal found 7/11![American Airlines logo]()
$338
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Fri 8/147:03 am
SJU
- MKE
1 stop11h 27m
American Airlines
Deal found 7/13![American Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:25 pm
MKE
- MBJ
2 stops19h 17m
American Airlines
Sat 8/225:08 pm
MBJ
- MKE
2 stops18h 29m
American Airlines
Deal found 7/12![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:21 am
MKE
- SJU
2 stops10h 34m
American Airlines
Fri 8/217:03 am
SJU
- MKE
1 stop11h 27m
American Airlines
Deal found 7/13![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:17 pm
MKE
- SJU
1 stop8h 37m
American Airlines
Fri 8/2812:55 am
SJU
- MKE
1 stop14h 17m
American Airlines
Deal found 7/15![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:00 am
MKE
- MBJ
1 stop8h 12m
American Airlines
Sat 8/2912:47 pm
MBJ
- MKE
1 stop10h 10m
American Airlines
Deal found 7/13![American Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:28 am
MKE
- SJU
1 stop16h 31m
American Airlines
Tue 9/11:38 pm
SJU
- MKE
2 stops10h 21m
American Airlines
Deal found 7/13![American Airlines logo]()
$353
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 July 16, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 16, 2026.
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:00 am
MKE
- SJU
1 stop15h 57m
American Airlines
Deal found 7/11![American Airlines logo]()
$163
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:28 am
MKE
- SJU
1 stop16h 31m
American Airlines
Deal found 7/12![American Airlines logo]()
$166
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
MKE
- SJU
1 stop16h 15m
American Airlines
Deal found 7/11![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:14 pm
MKE
- SJU
2 stops17h 36m
American Airlines
Deal found 7/11![American Airlines logo]()
$169
This American Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/83:53 pm
MKE
- MBJ
2 stops18h 50m
American Airlines
Deal found 7/14![American Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/141:55 pm
MKE
- SJU
1 stop7h 15m
Southwest
Deal found 7/13![Southwest logo]()
$173
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
MKE
- SJU
1 stop16h 15m
American Airlines
Deal found 7/13![American Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:27 pm
MKE
- SJU
2 stops16h 04m
American Airlines
Deal found 7/15![American Airlines logo]()
$179
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:34 am
MKE
- SXM
1 stop7h 19m
Delta
Deal found 7/15![Delta logo]()
$188
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:01 am
MKE
- SJU
2 stops12h 32m
American Airlines
Deal found 7/11![American Airlines logo]()
$188
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:15 am
MKE
- MBJ
2 stops8h 55m
United Airlines
Deal found 7/13![United Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:35 pm
MKE
- SXM
2 stops20h 45m
Southwest
Deal found 7/14![Southwest logo]()
$194
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 July 16, 2026.
Round-trip from | $326 (American Airlines) |
|---|---|
One-way from | $163 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $503 |
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 July 16, 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 - SJU
MKESJU
Milwaukee-Mitchell
Fri 9/11
11:00 am-11:05 pm
1 stop11h 05m
San Juan Luis Munoz Marin Intl
Sun 9/20
6:00 am-1:35 pm
1 stop8h 35m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 8/27
12:30 pm-11:05 pm
2 stops9h 35m
San Juan Luis Munoz Marin Intl
Mon 8/31
6:30 am-3:25 pm
2 stops9h 55m
$351
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/16
5:30 am-1:47 pm
1 stop7h 17m
San Juan Luis Munoz Marin Intl
Sun 9/20
2:59 pm-9:30 pm
1 stop7h 31m
$361
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 9/10
12:30 pm-11:05 pm
2 stops9h 35m
San Juan Luis Munoz Marin Intl
Sun 9/13
5:30 am-12:10 pm
1 stop7h 40m
$361
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/8
7:30 am-9:55 pm
1 stop13h 25m
San Juan Luis Munoz Marin Intl
Fri 8/14
10:00 am-4:20 pm
1 stop7h 20m
$361
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 11/2
12:45 pm-1:05 am
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Mon 11/9
6:35 am-12:05 pm
1 stop7h 30m
$363
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 9/17
10:11 am-10:19 pm
1 stop11h 08m
San Juan Luis Munoz Marin Intl
Tue 10/6
2:31 pm-9:02 pm
1 stop7h 31m
$371
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Fri 11/6
5:00 am-2:22 pm
1 stop8h 22m
Montego Bay Sangster Intl
Wed 11/11
10:56 am-11:59 pm
2 stops14h 03m
$397
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 10/10
6:15 am-2:44 pm
1 stop7h 29m
San Juan Luis Munoz Marin Intl
Tue 10/27
7:25 am-1:48 pm
1 stop7h 23m
$416
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 10/31
12:03 pm-11:36 pm
2 stops10h 33m
San Juan Luis Munoz Marin Intl
Sat 11/7
8:05 am-5:38 pm
2 stops11h 33m
$416
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-AUA
MKE-STT
MKE-SXM
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-AUA
MKE-STT
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $101). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $1,053). 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 July 16, 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.
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
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 July 16, 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 6 airlines flying from Milwaukee to Caribbean
Discover the top 6 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 July 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$143 | Average$585 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$564 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$623 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$706 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$853 | FlexibilityNo cancel fee | On-time83% |