$88+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
May 2 — May 91
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Caribbean with Cheapflights
1. Tell us where you want to go
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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 April 2, 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 April 2, 2026.
This Priceline deal was found by Cheapflights users on 4/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:47 pm
MKE
- SJU
1 stop7h 42m
Frontier
Mon 4/207:15 am
SJU
- MKE
1 stop7h 37m
Frontier
Deal found 4/1![Frontier logo]()
$291
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:34 pm
MKE
- SJU
1 stop13h 20m
Frontier
Sat 4/253:19 pm
SJU
- MKE
1 stop18h 19m
Frontier
Deal found 3/30![Frontier logo]()
$292
This Priceline deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/304:35 pm
MKE
- SJU
1 stop9h 04m
Multiple Airlines
Wed 5/63:13 am
SJU
- MKE
1 stop6h 48m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$294
This Priceline deal was found by Cheapflights users on 4/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:56 am
MKE
- SJU
1 stop21h 08m
Frontier
Tue 5/193:03 am
SJU
- MKE
1 stop29h 58m
Frontier
Deal found 4/1![Frontier logo]()
$295
This Priceline deal was found by Cheapflights users on 3/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:15 pm
MKE
- SJU
1 stop7h 36m
Frontier
Sun 4/196:30 am
SJU
- MKE
1 stop29h 56m
Frontier
Deal found 3/29![Frontier logo]()
$311
This CheapOair deal was found by Cheapflights users on 3/28. 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.
Sat 4/111:37 pm
MKE
- SJU
1 stop11h 24m
Frontier
Wed 4/1510:54 am
SJU
- MKE
1 stop25h 32m
Frontier
Deal found 3/28![Frontier logo]()
$313
This Priceline deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/48:46 am
MKE
- SJU
1 stop16h 22m
Frontier
Mon 6/86:09 pm
SJU
- MKE
1 stop14h 49m
Frontier
Deal found 3/31![Frontier logo]()
$315
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 6/48:46 am
MKE
- SJU
1 stop16h 22m
Frontier
Wed 6/106:00 am
SJU
- MKE
1 stop26h 58m
Frontier
Deal found 3/31![Frontier logo]()
$321
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2512:33 pm
MKE
- SJU
1 stop6h 51m
Delta
Fri 5/12:45 pm
SJU
- MKE
1 stop6h 50m
Delta
Deal found 3/31![Delta logo]()
$326
This CheapOair deal was found by Cheapflights users on 3/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:33 am
MKE
- SJU
1 stop15h 28m
Frontier
Sun 4/266:30 am
SJU
- MKE
1 stop29h 56m
Frontier
Deal found 3/29![Frontier logo]()
$328
This American Airlines deal was found by Cheapflights users on 3/29. 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 4/227:01 am
MKE
- SJU
2 stops12h 50m
American Airlines
Sat 5/26:45 am
SJU
- MKE
1 stop16h 42m
American Airlines
Deal found 3/29![American Airlines logo]()
$331
This FlightHub deal was found by Cheapflights users on 3/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:02 pm
MKE
- PUJ
2 stops19h 13m
Frontier
Sat 4/1811:07 am
PUJ
- MKE
1 stop22h 31m
Frontier
Deal found 3/28![Frontier logo]()
$341
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 April 2, 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 April 2, 2026.
This Delta deal was found by Cheapflights users on 3/28. 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 6/1610:08 am
MKE
- SJU
1 stop11h 19m
Delta
Tue 6/237:30 am
SJU
- MKE
1 stop10h 02m
Delta
Deal found 3/28![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 3/29. 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.
Fri 5/153:30 pm
MKE
- SJU
1 stop7h 10m
Southwest
Tue 5/195:35 am
SJU
- MKE
1 stop10h 40m
Southwest
Deal found 3/29![Southwest logo]()
$326
This American Airlines deal was found by Cheapflights users on 3/29. 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 5/65:06 am
MKE
- MBJ
2 stops8h 19m
American Airlines
Mon 5/114:37 pm
MBJ
- MKE
2 stops17h 32m
American Airlines
Deal found 3/29![American Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 4/1. 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 6/1810:38 am
MKE
- SJU
1 stop8h 56m
United Airlines
Sat 6/201:00 am
SJU
- MKE
2 stops11h 14m
United Airlines
Deal found 4/1![United Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:02 pm
MKE
- STT
1 stop17h 24m
Multiple Airlines
Sat 4/1812:25 pm
STT
- MKE
2 stops21h 13m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$410
This FlightHub deal was found by Cheapflights users on 4/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:13 pm
MKE
- PUJ
1 stop19h 41m
Frontier
Wed 4/299:13 pm
PUJ
- MKE
2 stops44h 15m
Frontier
Deal found 4/2![Frontier logo]()
$475
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/312:43 pm
MKE
- SJU
1 stop8h 34m
Delta
Thu 6/116:00 am
SJU
- MKE
1 stop8h 52m
Delta
Deal found 3/31![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 4/2. 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.
Sun 5/105:23 am
MKE
- SJU
1 stop7h 15m
Delta
Fri 5/157:30 am
SJU
- MKE
1 stop8h 42m
Delta
Deal found 4/2![Delta logo]()
$326
This FlightHub deal was found by Cheapflights users on 4/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:41 am
MKE
- CUR
2 stops28h 18m
JetBlue
Fri 6/123:02 pm
CUR
- MKE
2 stops18h 43m
JetBlue
Deal found 4/1![JetBlue logo]()
$745
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/92:15 pm
MKE
- SJU
2 stops8h 25m
Southwest
Sun 5/319:45 pm
SJU
- MKE
1 stop12h 55m
Southwest
Deal found 3/31![Southwest logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:02 pm
MKE
- STT
2 stops19h 26m
Multiple Airlines
Sun 4/1910:49 am
STT
- MKE
1 stop25h 37m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$423
This American Airlines deal was found by Cheapflights users on 4/1. 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 6/15:00 am
MKE
- MBJ
1 stop8h 30m
American Airlines
Fri 6/52:30 pm
MBJ
- MKE
1 stop17h 12m
American Airlines
Deal found 4/1![American Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:13 am
MKE
- MBJ
2 stops25h 13m
Delta
Thu 6/41:18 pm
MBJ
- MKE
1 stop10h 35m
Delta
Deal found 4/1![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/157:10 am
MKE
- SJU
2 stops11h 50m
Southwest
Fri 5/226:50 am
SJU
- MKE
1 stop13h 20m
Southwest
Deal found 3/31![Southwest logo]()
$406
This United Airlines deal was found by Cheapflights users on 3/28. 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 4/256:50 am
MKE
- MBJ
2 stops8h 20m
United Airlines
Sat 5/24:12 pm
MBJ
- MKE
2 stops15h 37m
United Airlines
Deal found 3/28![United Airlines logo]()
$467
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/296:00 am
MKE
- MBJ
1 stop8h 15m
American Airlines
Mon 5/44:37 pm
MBJ
- MKE
2 stops17h 32m
American Airlines
Deal found 4/1![American Airlines logo]()
$444
This United Airlines deal was found by Cheapflights users on 3/30. 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 5/276:39 pm
MKE
- MBJ
2 stops20h 31m
United Airlines
Thu 6/44:12 pm
MBJ
- MKE
2 stops17h 45m
United Airlines
Deal found 3/30![United Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 3/29. 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.
Sun 4/195:30 am
MKE
- SJU
1 stop9h 53m
Delta
Sat 4/256:15 am
SJU
- MKE
1 stop8h 37m
Delta
Deal found 3/29![Delta logo]()
$387
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Thu 8/277:10 am
MKE
- MBJ
1 stop26h 15m
American Airlines
Mon 8/312:30 pm
MBJ
- MKE
2 stops18h 47m
American Airlines
Deal found 4/1![American Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 3/30. 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.
Sun 7/511:25 am
MKE
- SJU
1 stop10h 10m
Southwest
Sun 7/126:05 am
SJU
- MKE
1 stop12h 40m
Southwest
Deal found 3/30![Southwest logo]()
$448
This United Airlines deal was found by Cheapflights users on 4/1. 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 5/282:50 pm
MKE
- MBJ
2 stops24h 20m
United Airlines
Thu 6/44:12 pm
MBJ
- MKE
2 stops17h 45m
United Airlines
Deal found 4/1![United Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 3/29. 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.
Wed 4/225:30 am
MKE
- STT
1 stop8h 18m
Delta
Tue 4/283:05 pm
STT
- MKE
1 stop9h 52m
Delta
Deal found 3/29![Delta logo]()
$400
This Southwest deal was found by Cheapflights users on 3/30. 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.
Sun 7/56:15 am
MKE
- SJU
2 stops16h 40m
Southwest
Wed 7/156:00 am
SJU
- MKE
1 stop12h 45m
Southwest
Deal found 3/30![Southwest logo]()
$448
This American Airlines deal was found by Cheapflights users on 3/28. 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 9/164:33 pm
MKE
- MBJ
2 stops18h 17m
American Airlines
Sun 9/203:15 pm
MBJ
- MKE
2 stops20h 47m
American Airlines
Deal found 3/28![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 3/28. 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.
Wed 4/2912:13 pm
MKE
- MBJ
2 stops25h 17m
United Airlines
Sun 5/32:40 pm
MBJ
- MKE
2 stops17h 09m
United Airlines
Deal found 3/28![United Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/147:00 am
MKE
- STT
1 stop6h 48m
Delta
Wed 4/223:05 pm
STT
- MKE
1 stop9h 52m
Delta
Deal found 3/31![Delta logo]()
$400
This Southwest deal was found by Cheapflights users on 3/28. 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.
Wed 6/107:45 am
MKE
- SJU
2 stops9h 40m
Southwest
Sun 6/149:05 pm
SJU
- MKE
1 stop13h 45m
Southwest
Deal found 3/28![Southwest logo]()
$456
This United Airlines deal was found by Cheapflights users on 3/29. 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.
Wed 4/2912:13 pm
MKE
- MBJ
2 stops25h 17m
United Airlines
Mon 5/42:40 pm
MBJ
- MKE
2 stops23h 47m
United Airlines
Deal found 3/29![United Airlines logo]()
$467
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Sat 9/55:51 pm
MKE
- GCM
2 stops17h 19m
American Airlines
Sat 9/1212:35 pm
GCM
- MKE
1 stop11h 35m
American Airlines
Deal found 3/28![American Airlines logo]()
$501
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Thu 5/288:45 pm
MKE
- MBJ
2 stops18h 25m
United Airlines
Fri 6/54:12 pm
MBJ
- MKE
2 stops18h 56m
United Airlines
Deal found 3/30![United Airlines logo]()
$467
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated April 2, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated April 2, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 3/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/104:26 pm
MKE
- SJU
1 stop7h 26m
Frontier
Sun 4/196:30 am
SJU
- MKE
1 stop29h 56m
Frontier
Deal found 3/29![Frontier logo]()
$333
This Priceline deal was found by Cheapflights users on 3/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:15 pm
MKE
- SJU
1 stop7h 36m
Frontier
Sun 4/196:30 am
SJU
- MKE
1 stop29h 56m
Frontier
Deal found 3/29![Frontier logo]()
$311
This CheapOair deal was found by Cheapflights users on 3/28. 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.
Sat 4/111:37 pm
MKE
- SJU
1 stop11h 24m
Frontier
Wed 4/1510:54 am
SJU
- MKE
1 stop25h 32m
Frontier
Deal found 3/28![Frontier logo]()
$313
This FlightHub deal was found by Cheapflights users on 3/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:02 pm
MKE
- PUJ
2 stops19h 13m
Frontier
Sat 4/1811:07 am
PUJ
- MKE
1 stop22h 31m
Frontier
Deal found 3/28![Frontier logo]()
$341
This Priceline deal was found by Cheapflights users on 4/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:47 pm
MKE
- SJU
1 stop7h 42m
Frontier
Mon 4/207:15 am
SJU
- MKE
1 stop7h 37m
Frontier
Deal found 4/1![Frontier logo]()
$291
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:34 pm
MKE
- SJU
1 stop13h 20m
Frontier
Sat 4/253:19 pm
SJU
- MKE
1 stop18h 19m
Frontier
Deal found 3/30![Frontier logo]()
$292
This CheapOair deal was found by Cheapflights users on 3/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:33 am
MKE
- SJU
1 stop15h 28m
Frontier
Sun 4/266:30 am
SJU
- MKE
1 stop29h 56m
Frontier
Deal found 3/29![Frontier logo]()
$328
This Frontier deal was found by Cheapflights users on 3/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:21 pm
MKE
- SJU
1 stop12h 40m
Frontier
Sun 4/263:21 am
SJU
- MKE
1 stop9h 05m
Frontier
Deal found 3/29![Frontier logo]()
$334
This American Airlines deal was found by Cheapflights users on 3/29. 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 4/227:01 am
MKE
- SJU
2 stops12h 50m
American Airlines
Sat 5/26:45 am
SJU
- MKE
1 stop16h 42m
American Airlines
Deal found 3/29![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2512:33 pm
MKE
- SJU
1 stop6h 51m
Delta
Fri 5/12:45 pm
SJU
- MKE
1 stop6h 50m
Delta
Deal found 3/31![Delta logo]()
$326
This Priceline deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/304:35 pm
MKE
- SJU
1 stop9h 04m
Multiple Airlines
Wed 5/63:13 am
SJU
- MKE
1 stop6h 48m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$294
This Priceline deal was found by Cheapflights users on 4/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:56 am
MKE
- SJU
1 stop21h 08m
Frontier
Tue 5/193:03 am
SJU
- MKE
1 stop29h 58m
Frontier
Deal found 4/1![Frontier logo]()
$295
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 April 2, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
This Orbitz deal was found by Cheapflights users on 3/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/39:33 am
MKE
- SJU
1 stop15h 28m
Frontier
Deal found 3/29![Frontier logo]()
$88
This Priceline deal was found by Cheapflights users on 4/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:56 am
MKE
- SJU
1 stop21h 08m
Frontier
Deal found 4/1![Frontier logo]()
$94
This Priceline deal was found by Cheapflights users on 3/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:47 pm
MKE
- SJU
1 stop7h 42m
Frontier
Deal found 3/28![Frontier logo]()
$98
This Expedia deal was found by Cheapflights users on 4/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:15 pm
MKE
- SJU
1 stop7h 36m
Frontier
Deal found 4/1![Frontier logo]()
$128
This Travelocity deal was found by Cheapflights users on 3/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:13 pm
MKE
- PUJ
1 stop19h 41m
Frontier
Deal found 3/29![Frontier logo]()
$130
This Priceline deal was found by Cheapflights users on 3/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:46 am
MKE
- SJU
1 stop13h 36m
Frontier
Deal found 3/28![Frontier logo]()
$132
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 5/206:42 pm
MKE
- MBJ
2 stops18h 26m
American Airlines
Deal found 3/30![American Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:30 am
MKE
- SJU
1 stop9h 53m
Delta
Deal found 4/1![Delta logo]()
$163
This American Airlines deal was found by Cheapflights users on 3/29. 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 5/27:01 am
MKE
- SJU
2 stops12h 50m
American Airlines
Deal found 3/29![American Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Fri 4/177:34 pm
MKE
- SJU
2 stops39h 49m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 9/216:41 pm
MKE
- SJU
2 stops16h 59m
American Airlines
Deal found 3/31![American Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 3/29. 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 6/249:35 am
MKE
- SJU
1 stop12h 10m
Southwest
Deal found 3/29![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 April 2, 2026.
Round-trip from | $291 (Priceline) |
|---|---|
One-way from | $88 (Orbitz) |
Popular in | December |
Cheapest in | September |
Average price | $373 |
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 April 2, 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 6/16
10:08 am-10:27 pm
1 stop11h 19m
San Juan Luis Munoz Marin Intl
Tue 6/23
7:30 am-4:32 pm
1 stop10h 02m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 5/15
3:30 pm-11:40 pm
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Tue 5/19
5:35 am-3:15 pm
1 stop10h 40m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 6/3
12:43 pm-10:17 pm
1 stop8h 34m
San Juan Luis Munoz Marin Intl
Thu 6/11
6:00 am-1:52 pm
1 stop8h 52m
$326
Quickest round-trip
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 5/10
5:23 am-1:38 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Fri 5/15
7:30 am-3:12 pm
1 stop8h 42m
$326
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 5/6
5:06 am-1:25 pm
2 stops8h 19m
Montego Bay Sangster Intl
Mon 5/11
4:37 pm-10:09 am
2 stops17h 32m
$362
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Tue 6/2
10:13 am-11:26 am
2 stops25h 13m
Montego Bay Sangster Intl
Thu 6/4
1:18 pm-11:53 pm
1 stop10h 35m
$367
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 6/18
10:38 am-8:34 pm
1 stop8h 56m
San Juan Luis Munoz Marin Intl
Sat 6/20
1:00 am-11:14 am
2 stops11h 14m
$375
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 5/9
2:15 pm-11:40 pm
2 stops8h 25m
San Juan Luis Munoz Marin Intl
Sun 5/31
9:45 pm-9:40 am
1 stop12h 55m
$387
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 4/19
5:30 am-4:23 pm
1 stop9h 53m
San Juan Luis Munoz Marin Intl
Sat 4/25
6:15 am-1:52 pm
1 stop8h 37m
$387
MilwaukeeSaint Thomas Island
MKE - STT
MKESTT
Milwaukee-Mitchell
Wed 4/22
5:30 am-2:48 pm
1 stop8h 18m
Saint Thomas Island Cyril E King
Tue 4/28
3:05 pm-11:57 pm
1 stop9h 52m
$400
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-STT
MKE-NAS
MKE-CUR
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-STT
MKE-NAS
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 $91). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $195). 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.
What is the cheapest time of day to fly from MKE to CB?
Find hourly flight availability from Milwaukee to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 2, 2026.
When flying from Milwaukee to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 April 2, 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
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Milwaukee to Caribbean flights
Consider these flights traveling from Milwaukee to Caribbean.
Top 7 airlines flying from Milwaukee to Caribbean
Discover the top 7 airlines that operate flights from Milwaukee to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$597 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$377 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$202 | Average$557 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$219 | Average$366 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$657 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$720 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |