$118+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jul 13 — Jul 201
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 June 13, 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 June 13, 2026.
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/255:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Tue 9/17:00 am
SJU
- MKE
1 stop11h 09m
United Airlines
Deal found 6/10![United Airlines logo]()
$226
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/156:00 am
MKE
- SJU
1 stop7h 44m
United Airlines
Sat 9/197:00 am
SJU
- MKE
1 stop11h 09m
United Airlines
Deal found 6/9![United Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/2212:58 pm
MKE
- SJU
2 stops9h 45m
American Airlines
Tue 8/253:47 pm
SJU
- MKE
1 stop8h 12m
American Airlines
Deal found 6/10![American Airlines logo]()
$276
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/126:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Tue 8/181:38 pm
SJU
- MKE
2 stops10h 21m
American Airlines
Deal found 6/10![American Airlines logo]()
$281
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 9/186:00 am
MKE
- SJU
1 stop7h 44m
United Airlines
Fri 10/23:56 pm
SJU
- MKE
1 stop8h 03m
United Airlines
Deal found 6/11![United Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/155:11 pm
MKE
- SJU
2 stops20h 39m
American Airlines
Sat 10/33:41 pm
SJU
- MKE
2 stops22h 07m
American Airlines
Deal found 6/11![American Airlines logo]()
$296
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/166:01 am
MKE
- SJU
2 stops13h 46m
American Airlines
Wed 9/306:27 am
SJU
- MKE
2 stops11h 14m
American Airlines
Deal found 6/11![American Airlines logo]()
$301
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 10/236:15 am
MKE
- SJU
1 stop7h 29m
United Airlines
Wed 10/281:05 am
SJU
- MKE
1 stop9h 41m
United Airlines
Deal found 6/11![United Airlines logo]()
$305
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 9/1610:43 am
MKE
- SJU
1 stop8h 55m
United Airlines
Fri 10/21:00 am
SJU
- MKE
2 stops11h 30m
United Airlines
Deal found 6/11![United Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/25:00 am
MKE
- SJU
2 stops12h 34m
American Airlines
Sun 9/610:33 am
SJU
- MKE
2 stops11h 33m
American Airlines
Deal found 6/10![American Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 6/11. 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 9/215:30 am
MKE
- SJU
1 stop10h 01m
Delta
Tue 9/295:41 pm
SJU
- MKE
1 stop7h 11m
Delta
Deal found 6/11![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 10/135:00 pm
MBJ
- MKE
2 stops19h 02m
American Airlines
Deal found 6/10![American Airlines logo]()
$357
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 June 13, 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 June 13, 2026.
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sun 8/235:55 am
MKE
- SJU
1 stop10h 10m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 6/11![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 6/12. 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.
Wed 8/1212:51 pm
MKE
- SJU
1 stop8h 38m
Delta
Tue 8/185:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/12![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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
MKE
- MBJ
1 stop8h 12m
American Airlines
Fri 9/1112:05 pm
MBJ
- MKE
1 stop9h 43m
American Airlines
Deal found 6/10![American Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/193:52 pm
MKE
- MBJ
2 stops19h 51m
United Airlines
Sat 9/262:40 pm
MBJ
- MKE
1 stop8h 05m
United Airlines
Deal found 6/10![United Airlines logo]()
$362
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/299:36 am
MKE
- STT
1 stop27h 27m
JetBlue
Fri 7/102:49 pm
STT
- MKE
2 stops18h 56m
JetBlue
Deal found 6/12![JetBlue logo]()
$576
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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
Sat 8/225:55 am
SJU
- MKE
1 stop7h 15m
Southwest
Deal found 6/9![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 6/13. 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 8/2311:50 am
MKE
- SJU
1 stop11h 00m
Southwest
Thu 8/2711:35 am
SJU
- MKE
2 stops9h 15m
Southwest
Deal found 6/13![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/115:00 am
MKE
- MBJ
2 stops10h 10m
United Airlines
Sat 7/184:12 pm
MBJ
- MKE
2 stops14h 48m
United Airlines
Deal found 6/10![United Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/195:43 pm
MKE
- MBJ
1 stop22h 33m
American Airlines
Sat 9/265:16 pm
MBJ
- MKE
2 stops17h 51m
American Airlines
Deal found 6/9![American Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/277:03 am
MKE
- MBJ
1 stop8h 31m
Delta
Mon 8/314:59 pm
MBJ
- MKE
1 stop6h 54m
Delta
Deal found 6/9![Delta logo]()
$422
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Sat 12/57:00 am
MKE
- MBJ
2 stops8h 12m
United Airlines
Sat 12/123:36 pm
MBJ
- MKE
1 stop8h 51m
United Airlines
Deal found 6/8![United Airlines logo]()
$421
This Delta deal was found by Cheapflights users on 6/12. 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.
Sat 9/193:59 pm
MKE
- MBJ
2 stops19h 26m
Delta
Fri 9/254:59 pm
MBJ
- MKE
1 stop6h 53m
Delta
Deal found 6/12![Delta logo]()
$427
This American Airlines deal was found by Cheapflights users on 6/11. 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 stops18h 37m
American Airlines
Tue 12/82:49 pm
STT
- MKE
2 stops11h 12m
American Airlines
Deal found 6/11![American Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 7/252:35 pm
MKE
- SJU
1 stop6h 50m
Southwest
Fri 7/318:15 pm
SJU
- MKE
1 stop13h 55m
Southwest
Deal found 6/11![Southwest logo]()
$420
This Delta deal was found by Cheapflights users on 6/12. 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.
Fri 9/184:36 pm
MKE
- MBJ
2 stops18h 49m
Delta
Sat 9/264:59 pm
MBJ
- MKE
1 stop16h 07m
Delta
Deal found 6/12![Delta logo]()
$427
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/101:17 pm
MKE
- SXM
2 stops23h 05m
American Airlines
Fri 8/212:42 pm
SXM
- MKE
2 stops21h 20m
American Airlines
Deal found 6/11![American Airlines logo]()
$446
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 6/3010:28 am
MKE
- SJU
1 stop9h 06m
United Airlines
Tue 7/71:00 am
SJU
- MKE
2 stops9h 53m
United Airlines
Deal found 6/12![United Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/1811:35 am
MKE
- SJU
1 stop9h 50m
Southwest
Tue 7/218:35 pm
SJU
- MKE
1 stop13h 15m
Southwest
Deal found 6/10![Southwest logo]()
$449
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/235:30 am
MKE
- STT
1 stop7h 14m
Delta
Wed 9/302:54 pm
STT
- MKE
1 stop6h 58m
Delta
Deal found 6/9![Delta logo]()
$469
This Justfly.com deal was found by Cheapflights users on 6/12. 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 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 6/12![JetBlue logo]()
$646
This American Airlines deal was found by Cheapflights users on 6/13. 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 8/112:49 pm
MKE
- GCM
2 stops20h 11m
American Airlines
Tue 8/182:10 pm
GCM
- MKE
2 stops8h 49m
American Airlines
Deal found 6/13![American Airlines logo]()
$504
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/243:15 pm
MKE
- SJU
1 stop7h 25m
Southwest
Thu 8/205:30 am
SJU
- MKE
1 stop7h 25m
Southwest
Deal found 6/9![Southwest logo]()
$471
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am
MKE
- GCM
1 stop5h 45m
United Airlines
Mon 12/145:45 pm
GCM
- MKE
2 stops17h 04m
United Airlines
Deal found 6/13![United Airlines logo]()
$556
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/235:53 pm
MKE
- STT
2 stops17h 58m
American Airlines
Wed 9/301:41 pm
STT
- MKE
2 stops22h 46m
American Airlines
Deal found 6/10![American Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/238:15 pm
MKE
- SJU
1 stop11h 45m
Southwest
Sun 7/269:05 pm
SJU
- MKE
1 stop13h 45m
Southwest
Deal found 6/10![Southwest logo]()
$492
This Delta deal was found by Cheapflights users on 6/11. 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.
Tue 8/115:34 am
MKE
- GCM
1 stop6h 05m
Delta
Tue 8/181:04 pm
GCM
- MKE
1 stop10h 49m
Delta
Deal found 6/11![Delta logo]()
$551
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 12/76:00 am
MKE
- PUJ
1 stop8h 02m
United Airlines
Thu 12/102:55 pm
PUJ
- MKE
1 stop9h 44m
United Airlines
Deal found 6/9![United Airlines logo]()
$564
This American Airlines deal was found by Cheapflights users on 6/11. 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 11/116:14 am
MKE
- PLS
1 stop7h 21m
American Airlines
Tue 11/173:36 pm
PLS
- MKE
1 stop9h 23m
American Airlines
Deal found 6/11![American Airlines logo]()
$528
This Delta deal was found by Cheapflights users on 6/12. 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.
Wed 12/95:45 am
MKE
- GCM
1 stop5h 40m
Delta
Wed 12/161:50 pm
GCM
- MKE
1 stop10h 59m
Delta
Deal found 6/12![Delta logo]()
$551
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 11/37:00 am
MKE
- PUJ
2 stops8h 25m
United Airlines
Wed 11/185:20 pm
PUJ
- MKE
3 stops20h 14m
United Airlines
Deal found 6/9![United Airlines logo]()
$569
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated June 13, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated June 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/8. 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 6/298:15 pm
MKE
- SJU
1 stop11h 45m
Southwest
Sat 7/46:00 am
SJU
- MKE
1 stop10h 30m
Southwest
Deal found 6/8![Southwest logo]()
$420
This Priceline deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:43 am
MKE
- SJU
1 stop16h 26m
Frontier
Wed 7/86:26 pm
SJU
- MKE
1 stop14h 32m
Frontier
Deal found 6/12![Frontier logo]()
$416
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 6/3010:28 am
MKE
- SJU
1 stop9h 06m
United Airlines
Tue 7/71:00 am
SJU
- MKE
2 stops9h 53m
United Airlines
Deal found 6/12![United Airlines logo]()
$447
This Priceline deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:53 am
MKE
- SJU
1 stop16h 16m
Frontier
Wed 7/86:26 pm
SJU
- MKE
1 stop14h 32m
Frontier
Deal found 6/12![Frontier logo]()
$446
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:46 am
MKE
- SJU
1 stop8h 52m
United Airlines
Sat 7/117:40 am
SJU
- MKE
1 stop8h 56m
United Airlines
Deal found 6/13![United Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/57:01 am
MKE
- SJU
1 stop14h 58m
American Airlines
Wed 7/157:00 am
SJU
- MKE
1 stop11h 17m
American Airlines
Deal found 6/10![American Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/56:15 am
MKE
- SJU
2 stops16h 40m
Southwest
Fri 7/1010:20 pm
SJU
- MKE
1 stop11h 50m
Southwest
Deal found 6/9![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/115:00 am
MKE
- MBJ
2 stops10h 10m
United Airlines
Sat 7/184:12 pm
MBJ
- MKE
2 stops14h 48m
United Airlines
Deal found 6/10![United Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 7/216:00 am
MKE
- SJU
1 stop15h 57m
American Airlines
Wed 7/297:00 am
SJU
- MKE
1 stop17h 44m
American Airlines
Deal found 6/12![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/286:00 am
MKE
- SJU
1 stop15h 57m
American Airlines
Wed 7/297:00 am
SJU
- MKE
1 stop17h 44m
American Airlines
Deal found 6/10![American Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/3012:58 pm
MKE
- SJU
1 stop8h 31m
Delta
Thu 8/612:56 pm
SJU
- MKE
1 stop8h 57m
Delta
Deal found 6/9![Delta logo]()
$380
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/307:01 am
MKE
- SJU
1 stop14h 58m
American Airlines
Thu 8/67:00 am
SJU
- MKE
1 stop17h 14m
American Airlines
Deal found 6/10![American Airlines logo]()
$409
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 June 13, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/198:20 am
MKE
- SJU
1 stop13h 55m
American Airlines
Deal found 6/10![American Airlines logo]()
$118
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/117:23 pm
MKE
- MBJ
2 stops16h 20m
United Airlines
Deal found 6/10![United Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 7/115:58 pm
MKE
- MBJ
2 stops17h 49m
American Airlines
Deal found 6/11![American Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/106:45 am
MKE
- SJU
1 stop8h 48m
Delta
Deal found 6/9![Delta logo]()
$163
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/10![American Airlines logo]()
$166
This American Airlines deal was found by Cheapflights users on 6/13. 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 7/216:00 am
MKE
- SJU
1 stop15h 57m
American Airlines
Deal found 6/13![American Airlines logo]()
$167
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 pm
MKE
- MBJ
1 stop19h 30m
United Airlines
Deal found 6/9![United Airlines logo]()
$171
This Priceline deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/308:43 am
MKE
- SJU
1 stop13h 46m
Frontier
Deal found 6/9![Frontier logo]()
$188
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 7/119:50 am
MKE
- SJU
1 stop12h 15m
Southwest
Deal found 6/11![Southwest logo]()
$203
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/38:43 am
MKE
- SJU
2 stops13h 16m
American Airlines
Deal found 6/12![American Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/296:48 pm
MKE
- PUJ
1 stop18h 17m
American Airlines
Deal found 6/10![American Airlines logo]()
$210
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Sat 7/186:20 am
MKE
- STT
1 stop7h 34m
United Airlines
Deal found 6/8![United 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 June 13, 2026.
Round-trip from | $226 (United Airlines) |
|---|---|
One-way from | $118 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $475 |
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 June 13, 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
Sun 8/23
5:55 am-5:05 pm
1 stop10h 10m
San Juan Luis Munoz Marin Intl
Sun 8/23
9:25 pm-8:55 am
1 stop12h 30m
$321
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 8/12
12:51 pm-10:29 pm
1 stop8h 38m
San Juan Luis Munoz Marin Intl
Tue 8/18
5:49 pm-11:53 pm
1 stop7h 04m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 8/14
1:55 pm-10:10 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Sat 8/22
5:55 am-12:10 pm
1 stop7h 15m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 8/23
11:50 am-11:50 pm
1 stop11h 00m
San Juan Luis Munoz Marin Intl
Thu 8/27
11:35 am-7:50 pm
2 stops9h 15m
$326
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Mon 9/7
5:00 am-1:12 pm
1 stop8h 12m
Montego Bay Sangster Intl
Fri 9/11
12:05 pm-9:48 pm
1 stop9h 43m
$357
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 9/19
3:52 pm-11:43 am
2 stops19h 51m
Montego Bay Sangster Intl
Sat 9/26
2:40 pm-10:45 pm
1 stop8h 05m
$362
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 7/11
5:00 am-3:10 pm
2 stops10h 10m
Montego Bay Sangster Intl
Sat 7/18
4:12 pm-7:00 am
2 stops14h 48m
$367
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 9/19
5:43 pm-4:16 pm
1 stop22h 33m
Montego Bay Sangster Intl
Sat 9/26
5:16 pm-11:07 am
2 stops17h 51m
$369
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 7/25
2:35 pm-10:25 pm
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Fri 7/31
8:15 pm-9:10 am
1 stop13h 55m
$420
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 12/5
7:00 am-4:12 pm
2 stops8h 12m
Montego Bay Sangster Intl
Sat 12/12
3:36 pm-11:27 pm
1 stop8h 51m
$421
Showing 1-10 of 58 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-PUJ
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-PUJ
MKE-STT
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, October is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $108). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $1,030). 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 June 13, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 13, 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 June 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$574 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$554 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$670 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$316 | Average$734 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |