$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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Aug 2 — Aug 91
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 3, 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 3, 2026.
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:03 am
MKE
- SJU
1 stop8h 35m
Delta
Tue 8/255:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/29![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 33m
American Airlines
Sun 9/67:03 am
SJU
- MKE
1 stop11h 27m
American Airlines
Deal found 7/3![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
1 stop16h 42m
American Airlines
Fri 10/3012:13 pm
SJU
- MKE
1 stop12h 44m
American Airlines
Deal found 6/30![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 33m
American Airlines
Mon 9/77:03 am
SJU
- MKE
1 stop15h 03m
American Airlines
Deal found 6/29![American Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:40 am
MKE
- SJU
2 stops10h 30m
Southwest
Mon 10/59:45 pm
SJU
- MKE
1 stop12h 10m
Southwest
Deal found 6/29![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:37 am
MKE
- SJU
1 stop8h 23m
United Airlines
Tue 11/108:05 am
SJU
- MKE
2 stops11h 33m
United Airlines
Deal found 6/28![United Airlines logo]()
$348
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Mon 9/71:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 7/2![United Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1010:42 am
MKE
- SJU
2 stops12h 08m
United Airlines
Sun 10/253:55 pm
SJU
- MKE
1 stop7h 50m
United Airlines
Deal found 6/28![United Airlines logo]()
$353
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:00 am
MKE
- SJU
2 stops14h 38m
United Airlines
Sun 10/43:56 pm
SJU
- MKE
1 stop8h 03m
United Airlines
Deal found 6/29![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:00 pm
MKE
- SJU
1 stop7h 36m
United Airlines
Mon 12/72:05 am
SJU
- MKE
1 stop9h 41m
United Airlines
Deal found 7/2![United Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:00 am
MKE
- SJU
2 stops10h 05m
Southwest
Wed 8/261:45 pm
SJU
- MKE
2 stops8h 40m
Southwest
Deal found 6/29![Southwest logo]()
$363
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am
MKE
- MBJ
1 stop7h 12m
American Airlines
Fri 9/1112:05 pm
MBJ
- MKE
1 stop9h 43m
American Airlines
Deal found 7/1![American Airlines logo]()
$372
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 3, 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 3, 2026.
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:30 am
MKE
- SJU
1 stop10h 19m
Delta
Sat 10/175:43 pm
SJU
- MKE
1 stop7h 10m
Delta
Deal found 7/2![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:35 am
MKE
- SJU
1 stop10h 20m
Southwest
Wed 9/305:15 am
SJU
- MKE
1 stop6h 40m
Southwest
Deal found 6/28![Southwest logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:14 pm
MKE
- MBJ
2 stops16h 39m
American Airlines
Tue 10/135:13 pm
MBJ
- MKE
2 stops18h 55m
American Airlines
Deal found 7/2![American Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Fri 10/161:00 am
SJU
- MKE
2 stops11h 30m
United Airlines
Deal found 7/2![United Airlines logo]()
$416
This Justfly.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 6/28![JetBlue logo]()
$626
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:30 am
MKE
- SJU
1 stop9h 35m
Southwest
Sat 8/228:20 am
SJU
- MKE
1 stop10h 10m
Southwest
Deal found 6/28![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:55 pm
MKE
- SJU
1 stop6h 24m
Delta
Sun 9/202:59 pm
SJU
- MKE
1 stop7h 31m
Delta
Deal found 6/30![Delta logo]()
$345
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:50 am
MKE
- SJU
2 stops11h 34m
United Airlines
Sat 11/78:05 am
SJU
- MKE
2 stops11h 33m
United Airlines
Deal found 7/2![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 7/2![American Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:00 am
MKE
- SJU
2 stops14h 38m
United Airlines
Fri 10/161:00 am
SJU
- MKE
2 stops11h 30m
United Airlines
Deal found 7/2![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:25 pm
MKE
- GCM
2 stops18h 35m
American Airlines
Fri 8/212:10 pm
GCM
- MKE
2 stops17h 39m
American Airlines
Deal found 6/30![American Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:40 am
MKE
- MBJ
1 stop7h 40m
Delta
Sat 10/244:49 pm
MBJ
- MKE
1 stop16h 17m
Delta
Deal found 6/28![Delta logo]()
$442
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:30 am
MKE
- SJU
1 stop9h 30m
United Airlines
Wed 11/188:05 am
SJU
- MKE
2 stops11h 33m
United Airlines
Deal found 7/2![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:01 am
MKE
- MBJ
1 stop8h 11m
American Airlines
Sun 9/1312:05 pm
MBJ
- MKE
1 stop9h 43m
American Airlines
Deal found 7/1![American Airlines logo]()
$452
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Sun 9/202:55 pm
SJU
- MKE
1 stop9h 42m
United Airlines
Deal found 7/2![United Airlines logo]()
$416
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:20 pm
MKE
- STT
2 stops19h 30m
Southwest
Mon 9/212:35 pm
STT
- MKE
1 stop7h 10m
Southwest
Deal found 6/29![Southwest logo]()
$529
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:48 pm
MKE
- MBJ
1 stop18h 24m
American Airlines
Mon 8/312:12 pm
MBJ
- MKE
1 stop17h 37m
American Airlines
Deal found 7/2![American Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:34 am
MKE
- GCM
1 stop6h 05m
Delta
Tue 8/181:04 pm
GCM
- MKE
1 stop10h 49m
Delta
Deal found 6/28![Delta logo]()
$501
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:15 am
MKE
- SJU
1 stop7h 29m
United Airlines
Fri 10/161:00 am
SJU
- MKE
2 stops11h 30m
United Airlines
Deal found 7/2![United Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
MKE
- GCM
1 stop5h 39m
Delta
Sat 8/291:04 pm
GCM
- MKE
1 stop7h 05m
Delta
Deal found 7/2![Delta logo]()
$501
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:00 am
MKE
- SXM
1 stop9h 05m
Southwest
Wed 7/293:00 pm
SXM
- MKE
1 stop8h 50m
Southwest
Deal found 6/29![Southwest logo]()
$552
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:11 pm
MKE
- MBJ
1 stop22h 44m
American Airlines
Sat 12/121:45 pm
MBJ
- MKE
1 stop21h 00m
American Airlines
Deal found 6/30![American Airlines logo]()
$464
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:30 am
MKE
- SJU
1 stop9h 30m
United Airlines
Mon 11/24:55 pm
SJU
- MKE
1 stop7h 50m
United Airlines
Deal found 7/1![United Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:30 am
MKE
- GCM
1 stop6h 10m
Delta
Sat 9/191:05 pm
GCM
- MKE
1 stop7h 27m
Delta
Deal found 6/28![Delta logo]()
$501
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:19 pm
MKE
- SXM
2 stops19h 01m
American Airlines
Tue 11/173:20 pm
SXM
- MKE
2 stops21h 52m
American Airlines
Deal found 7/1![American Airlines logo]()
$475
This United Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:30 am
MKE
- MBJ
1 stop6h 18m
United Airlines
Sun 11/12:54 pm
MBJ
- MKE
1 stop7h 01m
United Airlines
Deal found 6/28![United Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:30 am
MKE
- GCM
1 stop6h 10m
Delta
Sun 9/271:00 pm
GCM
- MKE
1 stop7h 55m
Delta
Deal found 7/2![Delta logo]()
$501
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:35 am
MKE
- STT
1 stop7h 15m
Southwest
Sun 8/302:10 pm
STT
- MKE
1 stop9h 15m
Southwest
Deal found 6/30![Southwest logo]()
$618
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:21 am
MKE
- SXM
1 stop28h 21m
American Airlines
Sun 8/232:22 pm
SXM
- MKE
2 stops20h 29m
American Airlines
Deal found 7/2![American Airlines logo]()
$483
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/265:45 am
MKE
- STT
1 stop7h 38m
Delta
Thu 8/272:49 pm
STT
- MKE
1 stop7h 04m
Delta
Deal found 6/28![Delta logo]()
$512
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 3, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:43 am
MKE
- SJU
1 stop16h 32m
Frontier
Wed 7/298:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/28![Frontier logo]()
$386
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:15 pm
MKE
- SJU
1 stop11h 45m
Southwest
Mon 8/310:20 pm
SJU
- MKE
1 stop13h 35m
Southwest
Deal found 6/29![Southwest logo]()
$385
This Frontier deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:43 am
MKE
- SJU
1 stop7h 48m
Frontier
Sat 8/88:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/28![Frontier logo]()
$396
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:00 am
MKE
- SJU
1 stop15h 57m
American Airlines
Fri 8/213:47 pm
SJU
- MKE
1 stop8h 12m
American Airlines
Deal found 7/2![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:20 am
MKE
- SJU
2 stops11h 13m
American Airlines
Fri 8/217:30 am
SJU
- MKE
1 stop16h 29m
American Airlines
Deal found 6/28![American Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:00 am
MKE
- SJU
2 stops10h 05m
Southwest
Wed 8/261:45 pm
SJU
- MKE
2 stops8h 40m
Southwest
Deal found 6/29![Southwest logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Mon 8/318:57 pm
SJU
- MKE
1 stop15h 16m
Frontier
Deal found 7/2![Frontier logo]()
$399
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:51 pm
MKE
- SJU
1 stop8h 38m
Delta
Tue 9/81:21 pm
SJU
- MKE
1 stop8h 15m
Delta
Deal found 6/28![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:34 am
MKE
- SJU
1 stop7h 08m
Delta
Sun 9/65:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 7/2![Delta logo]()
$376
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:03 am
MKE
- SJU
1 stop8h 35m
Delta
Tue 8/255:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/29![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:34 am
MKE
- SJU
1 stop10h 04m
Delta
Wed 9/97:00 am
SJU
- MKE
1 stop11h 32m
Delta
Deal found 6/28![Delta logo]()
$383
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 pm
MKE
- MBJ
2 stops17h 37m
American Airlines
Mon 8/315:08 pm
MBJ
- MKE
2 stops18h 29m
American Airlines
Deal found 6/30![American Airlines logo]()
$377
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 3, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This American Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:00 am
MKE
- MBJ
1 stop7h 06m
American Airlines
Deal found 6/29![American Airlines logo]()
$162
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:30 am
MKE
- SJU
2 stops14h 20m
United Airlines
Deal found 6/30![United Airlines logo]()
$163
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:28 am
MKE
- SJU
1 stop7h 23m
American Airlines
Deal found 6/30![American Airlines logo]()
$166
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/166:20 am
MKE
- SJU
2 stops11h 13m
American Airlines
Deal found 7/3![American Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:28 am
MKE
- SJU
2 stops11h 05m
American Airlines
Deal found 6/28![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:14 pm
MKE
- SJU
2 stops18h 26m
American Airlines
Deal found 7/1![American Airlines logo]()
$169
This American Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
2 stops11h 05m
American Airlines
Deal found 6/29![American Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:43 am
MKE
- SJU
2 stops14h 24m
Frontier
Deal found 6/28![Frontier logo]()
$175
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:51 pm
MKE
- SJU
1 stop8h 38m
Delta
Deal found 6/29![Delta logo]()
$182
This Travelocity deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:43 am
MKE
- SJU
1 stop16h 32m
Frontier
Deal found 6/30![Frontier logo]()
$188
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:56 pm
MKE
- SJU
1 stop10h 33m
United Airlines
Deal found 6/30![United Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:10 am
MKE
- MBJ
1 stop6h 40m
Southwest
Deal found 7/1![Southwest logo]()
$192
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 3, 2026.
Round-trip from | $326 (Delta) |
|---|---|
One-way from | $162 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $489 |
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 3, 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
Tue 9/29
5:30 am-4:49 pm
1 stop10h 19m
San Juan Luis Munoz Marin Intl
Sat 10/17
5:43 pm-11:53 pm
1 stop7h 10m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 9/14
5:35 am-4:55 pm
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Wed 9/30
5:15 am-10:55 am
1 stop6h 40m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/18
10:30 am-9:05 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Sat 8/22
8:20 am-5:30 pm
1 stop10h 10m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/16
2:55 pm-10:19 pm
1 stop6h 24m
San Juan Luis Munoz Marin Intl
Sun 9/20
2:59 pm-9:30 pm
1 stop7h 31m
$345
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 10/3
8:14 pm-12:53 pm
2 stops16h 39m
Montego Bay Sangster Intl
Tue 10/13
5:13 pm-12:08 pm
2 stops18h 55m
$377
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 10/3
5:00 am-2:44 pm
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Fri 10/16
1:00 am-11:30 am
2 stops11h 30m
$416
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 10/31
7:50 am-8:24 pm
2 stops11h 34m
San Juan Luis Munoz Marin Intl
Sat 11/7
8:05 am-5:38 pm
2 stops11h 33m
$416
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 9/29
5:00 am-8:38 pm
2 stops14h 38m
San Juan Luis Munoz Marin Intl
Fri 10/16
1:00 am-11:30 am
2 stops11h 30m
$416
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 11/3
9:30 am-9:00 pm
1 stop9h 30m
San Juan Luis Munoz Marin Intl
Wed 11/18
8:05 am-5:38 pm
2 stops11h 33m
$416
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/16
5:00 am-2:44 pm
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Sun 9/20
2:55 pm-11:37 pm
1 stop9h 42m
$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-GCM
MKE-STT
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-GCM
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 $1,063). 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 3, 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
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 3, 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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$582 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$557 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$624 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$713 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$866 | FlexibilityNo cancel fee | On-time83% |