$101+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Mar 15 — Mar 221
1 adult, Economy
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Find cheap flights from Milwaukee to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Milwaukee to CaribbeanExplore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 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 February 13, 2026.
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:01 pm
MKE
- SJU
1 stop10h 53m
Frontier
Thu 3/123:08 am
SJU
- MKE
1 stop9h 28m
Frontier
Deal found 2/11![Frontier logo]()
$276
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:35 pm
MKE
- SJU
1 stop6h 23m
Frontier
Sun 3/153:08 am
SJU
- MKE
1 stop9h 33m
Frontier
Deal found 2/10![Frontier logo]()
$278
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 5/46:49 am
MKE
- SJU
1 stop6h 55m
United Airlines
Fri 5/81:00 am
SJU
- MKE
2 stops14h 27m
United Airlines
Deal found 2/10![United Airlines logo]()
$279
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:47 pm
MKE
- SJU
1 stop17h 04m
Frontier
Wed 3/116:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 2/11![Frontier logo]()
$280
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/44:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Wed 3/116:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 2/10![Frontier logo]()
$288
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:42 pm
MKE
- SJU
1 stop16h 17m
Frontier
Mon 5/47:15 am
SJU
- MKE
1 stop12h 32m
Frontier
Deal found 2/11![Frontier logo]()
$291
This Southwest deal was found by Cheapflights users on 2/11. 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 5/25:00 am
MKE
- SJU
1 stop13h 05m
Southwest
Sun 5/1011:40 am
SJU
- MKE
1 stop13h 05m
Southwest
Deal found 2/11![Southwest logo]()
$295
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:01 pm
MKE
- SJU
1 stop16h 08m
Frontier
Sun 3/156:30 am
SJU
- MKE
1 stop30h 11m
Frontier
Deal found 2/10![Frontier logo]()
$296
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/44:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Mon 3/95:30 am
SJU
- MKE
1 stop12h 32m
Frontier
Deal found 2/10![Frontier logo]()
$297
This CheapOair deal was found by Cheapflights users on 2/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:35 pm
MKE
- SJU
1 stop15h 19m
Frontier
Tue 3/243:08 am
SJU
- MKE
1 stop29h 22m
Frontier
Deal found 2/12![Frontier logo]()
$298
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:47 pm
MKE
- SJU
1 stop24h 19m
Frontier
Wed 3/116:30 am
SJU
- MKE
1 stop26h 00m
Frontier
Deal found 2/11![Frontier logo]()
$304
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/167:52 pm
MKE
- SJU
1 stop28h 56m
Frontier
Thu 2/196:00 am
SJU
- MKE
1 stop29h 43m
Frontier
Deal found 2/10![Frontier logo]()
$305
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 February 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 February 13, 2026.
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 5/46:49 am
MKE
- SJU
1 stop6h 55m
United Airlines
Fri 5/81:00 am
SJU
- MKE
2 stops14h 27m
United Airlines
Deal found 2/10![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 2/11. 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 5/25:00 am
MKE
- SJU
1 stop13h 05m
Southwest
Sun 5/1011:40 am
SJU
- MKE
1 stop13h 05m
Southwest
Deal found 2/11![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 2/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/111:40 pm
MKE
- SJU
1 stop8h 35m
Delta
Sat 4/186:15 am
SJU
- MKE
1 stop11h 09m
Delta
Deal found 2/10![Delta logo]()
$318
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:06 am
MKE
- MBJ
2 stops8h 19m
American Airlines
Wed 4/1512:56 pm
MBJ
- MKE
2 stops10h 01m
American Airlines
Deal found 2/12![American Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:20 pm
MKE
- STT
2 stops18h 11m
Multiple Airlines
Tue 3/33:36 pm
STT
- MKE
1 stop26h 08m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 2/12. 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 4/171:10 pm
MKE
- SJU
1 stop7h 55m
American Airlines
Sat 4/253:19 pm
SJU
- MKE
1 stop7h 22m
American Airlines
Deal found 2/12![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 2/9. 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.
Mon 6/157:00 am
MKE
- SJU
1 stop13h 15m
Southwest
Mon 6/225:15 pm
SJU
- MKE
1 stop7h 35m
Southwest
Deal found 2/9![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 2/9. 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 3/29:44 am
MKE
- SJU
2 stops12h 52m
United Airlines
Tue 3/32:05 am
SJU
- MKE
2 stops12h 30m
United Airlines
Deal found 2/9![United Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 2/12. 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.
Thu 3/1212:11 pm
MKE
- SJU
1 stop10h 04m
Delta
Thu 3/195:30 pm
SJU
- MKE
1 stop7h 28m
Delta
Deal found 2/12![Delta logo]()
$370
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:41 pm
MKE
- MBJ
2 stops15h 32m
American Airlines
Sat 4/1810:13 am
MBJ
- MKE
2 stops12h 10m
American Airlines
Deal found 2/12![American Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:45 am
MKE
- SJU
1 stop12h 00m
Southwest
Wed 7/291:30 pm
SJU
- MKE
1 stop10h 15m
Southwest
Deal found 2/11![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 2/9. 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 4/115:10 am
MKE
- SJU
2 stops14h 28m
United Airlines
Tue 4/141:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 2/9![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
MKE
- MBJ
1 stop8h 15m
American Airlines
Mon 5/114:37 pm
MBJ
- MKE
2 stops17h 32m
American Airlines
Deal found 2/12![American Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:11 pm
MKE
- STT
1 stop16h 20m
Multiple Airlines
Fri 3/65:40 pm
STT
- MKE
2 stops20h 39m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$421
This Delta deal was found by Cheapflights users on 2/12. 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 5/65:21 am
MKE
- MBJ
1 stop9h 56m
Delta
Mon 5/114:55 pm
MBJ
- MKE
1 stop7h 01m
Delta
Deal found 2/12![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 2/10. 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 5/283:30 pm
MKE
- SJU
1 stop7h 10m
Southwest
Thu 6/410:20 am
SJU
- MKE
1 stop10h 00m
Southwest
Deal found 2/10![Southwest logo]()
$358
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Thu 3/127:00 am
MKE
- PLS
2 stops8h 00m
United Airlines
Thu 3/192:23 pm
PLS
- MKE
1 stop7h 22m
United Airlines
Deal found 2/10![United Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 2/11. 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.
Wed 3/115:45 am
MKE
- PLS
1 stop6h 05m
Delta
Wed 3/182:15 pm
PLS
- MKE
1 stop7h 40m
Delta
Deal found 2/11![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:37 pm
MKE
- PLS
1 stop16h 23m
American Airlines
Mon 3/303:30 pm
PLS
- MKE
1 stop9h 15m
American Airlines
Deal found 2/12![American Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:26 pm
MKE
- STT
2 stops20h 00m
Multiple Airlines
Wed 4/152:36 pm
STT
- MKE
1 stop21h 32m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$463
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:41 pm
MKE
- MBJ
1 stop14h 32m
American Airlines
Tue 4/142:19 pm
MBJ
- MKE
1 stop7h 38m
American Airlines
Deal found 2/11![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 2/12. 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.
Mon 4/205:21 am
MKE
- NAS
1 stop7h 42m
Delta
Thu 4/233:28 pm
NAS
- MKE
1 stop6h 07m
Delta
Deal found 2/12![Delta logo]()
$420
This Southwest deal was found by Cheapflights users on 2/10. 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.
Mon 4/135:30 am
MKE
- NAS
1 stop6h 45m
Southwest
Thu 4/168:45 am
NAS
- MKE
2 stops9h 35m
Southwest
Deal found 2/10![Southwest logo]()
$424
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/74:47 pm
MKE
- PLS
2 stops17h 31m
American Airlines
Sat 3/145:11 pm
PLS
- MKE
1 stop18h 50m
American Airlines
Deal found 2/12![American Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 2/10. 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.
Sun 4/125:00 am
MKE
- NAS
1 stop7h 20m
Southwest
Wed 4/158:45 am
NAS
- MKE
2 stops13h 50m
Southwest
Deal found 2/10![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 2/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/135:45 am
MKE
- STX
1 stop6h 33m
Delta
Sun 3/152:24 pm
STX
- MKE
1 stop7h 31m
Delta
Deal found 2/10![Delta logo]()
$426
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:10 am
MKE
- PLS
2 stops8h 20m
American Airlines
Wed 3/181:20 pm
PLS
- MKE
2 stops10h 47m
American Airlines
Deal found 2/13![American Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:30 am
MKE
- NAS
1 stop12h 00m
Southwest
Thu 4/232:10 pm
NAS
- MKE
2 stops9h 50m
Southwest
Deal found 2/12![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 2/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:45 am
MKE
- STX
1 stop6h 33m
Delta
Thu 3/192:24 pm
STX
- MKE
1 stop7h 31m
Delta
Deal found 2/10![Delta logo]()
$426
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/114:26 pm
MKE
- PLS
2 stops18h 59m
American Airlines
Mon 4/203:23 pm
PLS
- MKE
2 stops20h 20m
American Airlines
Deal found 2/10![American Airlines logo]()
$384
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated February 13, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated February 13, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1310:38 am
MKE
- SJU
1 stop14h 15m
Frontier
Tue 3/35:25 pm
SJU
- MKE
1 stop24h 19m
Frontier
Deal found 2/10![Frontier logo]()
$307
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/167:52 pm
MKE
- SJU
1 stop28h 56m
Frontier
Thu 2/196:00 am
SJU
- MKE
1 stop29h 43m
Frontier
Deal found 2/10![Frontier logo]()
$305
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2010:38 am
MKE
- SJU
1 stop12h 05m
Frontier
Tue 2/245:25 pm
SJU
- MKE
1 stop24h 19m
Frontier
Deal found 2/10![Frontier logo]()
$309
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/44:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Wed 3/116:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 2/10![Frontier logo]()
$288
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/44:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Mon 3/95:30 am
SJU
- MKE
1 stop12h 32m
Frontier
Deal found 2/10![Frontier logo]()
$297
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:47 pm
MKE
- SJU
1 stop24h 19m
Frontier
Wed 3/116:30 am
SJU
- MKE
1 stop26h 00m
Frontier
Deal found 2/11![Frontier logo]()
$304
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:47 pm
MKE
- SJU
1 stop17h 04m
Frontier
Wed 3/116:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 2/11![Frontier logo]()
$280
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:01 pm
MKE
- SJU
1 stop10h 53m
Frontier
Thu 3/123:08 am
SJU
- MKE
1 stop9h 28m
Frontier
Deal found 2/11![Frontier logo]()
$276
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:01 pm
MKE
- SJU
1 stop16h 08m
Frontier
Sun 3/156:30 am
SJU
- MKE
1 stop30h 11m
Frontier
Deal found 2/10![Frontier logo]()
$296
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:35 pm
MKE
- SJU
1 stop6h 23m
Frontier
Sun 3/153:08 am
SJU
- MKE
1 stop9h 33m
Frontier
Deal found 2/10![Frontier logo]()
$278
This CheapOair deal was found by Cheapflights users on 2/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:35 pm
MKE
- SJU
1 stop6h 23m
Frontier
Sun 3/156:30 am
SJU
- MKE
1 stop30h 11m
Frontier
Deal found 2/9![Frontier logo]()
$316
This CheapOair deal was found by Cheapflights users on 2/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:35 pm
MKE
- SJU
1 stop15h 19m
Frontier
Tue 3/243:08 am
SJU
- MKE
1 stop29h 22m
Frontier
Deal found 2/12![Frontier logo]()
$298
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 February 13, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
This Priceline deal was found by Cheapflights users on 2/12. 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.
Mon 3/28:11 pm
MKE
- SJU
1 stop11h 43m
Frontier
Deal found 2/12![Frontier logo]()
$101
This Orbitz deal was found by Cheapflights users on 2/12. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:42 pm
MKE
- SJU
1 stop18h 00m
Frontier
Deal found 2/12![Frontier logo]()
$107
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:00 am
MKE
- PUJ
Nonstop4h 35m
Sun Country Air
Deal found 2/11![Sun Country Air logo]()
$116
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/238:20 pm
MKE
- SJU
1 stop12h 37m
Frontier
Deal found 2/10![Frontier logo]()
$120
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:47 pm
MKE
- SJU
1 stop15h 40m
Frontier
Deal found 2/10![Frontier logo]()
$122
This Expedia deal was found by Cheapflights users on 2/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/168:20 pm
MKE
- SJU
1 stop28h 43m
Frontier
Deal found 2/9![Frontier logo]()
$126
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/248:49 am
MKE
- SJU
2 stops11h 01m
American Airlines
Deal found 2/10![American Airlines logo]()
$133
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:06 am
MKE
- SJU
2 stops11h 06m
American Airlines
Deal found 2/12![American Airlines logo]()
$136
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Tue 3/1712:14 pm
MKE
- SJU
2 stops9h 44m
American Airlines
Deal found 2/9![American Airlines logo]()
$137
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/299:01 pm
MKE
- SJU
1 stop10h 53m
Frontier
Deal found 2/11![Frontier logo]()
$138
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:02 pm
MKE
- SJU
1 stop27h 38m
Frontier
Deal found 2/11![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:35 pm
MKE
- STT
1 stop17h 56m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$167
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 February 13, 2026.
Round-trip from | $276 (Priceline) |
|---|---|
One-way from | $101 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $492 |
Good round-trip deal | $628 or less |
Good one-way deal | $230 or less |
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 February 13, 2026.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.
Fly from
Milwaukee
Fly to
Caribbean
Route
Depart
Return
Price
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 5/4
6:49 am-2:44 pm
1 stop6h 55m
San Juan Luis Munoz Marin Intl
Fri 5/8
1:00 am-2:27 pm
2 stops14h 27m
$279
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 5/2
5:00 am-7:05 pm
1 stop13h 05m
San Juan Luis Munoz Marin Intl
Sun 5/10
11:40 am-11:45 pm
1 stop13h 05m
$295
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 4/11
1:40 pm-11:15 pm
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Sat 4/18
6:15 am-4:24 pm
1 stop11h 09m
$318
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sun 4/12
5:06 am-1:25 pm
2 stops8h 19m
Montego Bay Sangster Intl
Wed 4/15
12:56 pm-10:57 pm
2 stops10h 01m
$319
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 4/17
1:10 pm-10:05 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Sat 4/25
3:19 pm-9:41 pm
1 stop7h 22m
$329
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 6/15
7:00 am-9:15 pm
1 stop13h 15m
San Juan Luis Munoz Marin Intl
Mon 6/22
5:15 pm-11:50 pm
1 stop7h 35m
$342
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 4/11
5:41 pm-9:13 am
2 stops15h 32m
Montego Bay Sangster Intl
Sat 4/18
10:13 am-10:23 pm
2 stops12h 10m
$344
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 5/6
6:00 am-2:15 pm
1 stop8h 15m
Montego Bay Sangster Intl
Mon 5/11
4:37 pm-10:09 am
2 stops17h 32m
$344
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 7/22
6:45 am-7:45 pm
1 stop12h 00m
San Juan Luis Munoz Marin Intl
Wed 7/29
1:30 pm-10:45 pm
1 stop10h 15m
$347
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 3/2
9:44 am-12:36 am
2 stops12h 52m
San Juan Luis Munoz Marin Intl
Tue 3/3
2:05 am-12:35 pm
2 stops12h 30m
$356
Showing 1-10 of 60 results
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-PUJ
MKE-STT
MKE-MBJ
MKE-AUA
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-PUJ
MKE-STT
MKE-MBJ
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 February 13, 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 February 13, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 February 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 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 February 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$85 | Average$298 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$564 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$182 | Average$576 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$195 | Average$351 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$266 | Average$658 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$748 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$778 | FlexibilityNo cancel fee | On-time83% |