$105+ Cheap flights from Milwaukee (MKE) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 3 — Nov 101
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
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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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 October 4, 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 October 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:15 am -
1 stop14h 35m
Mon 11/97:26 pm -
1 stop15h 50m
Deal found 9/29![Frontier logo]()
$255
This FlightHub deal was found by Cheapflights users on 10/1. 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.
Thu 11/1210:15 am -
1 stop14h 35m
Sat 11/143:55 am -
1 stop7h 21m
Deal found 10/1![Frontier logo]()
$291
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop14h 35m
Mon 11/211:20 am -
1 stop23h 56m
Deal found 9/30![Frontier logo]()
$305
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:15 am -
1 stop14h 38m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 9/30![Frontier logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Mon 12/75:24 pm -
1 stop30h 49m
Wed 12/93:43 am -
1 stop14h 55m
Deal found 9/29![Frontier logo]()
$348
This Frontier deal was found by Cheapflights users on 9/29. 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.
Thu 10/1510:15 am -
1 stop11h 50m
Mon 10/262:58 am -
1 stop7h 18m
Deal found 9/29![Frontier logo]()
$349
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop27h 21m
Mon 10/197:44 pm -
1 stop14h 36m
Deal found 9/29![Frontier logo]()
$359
This Southwest deal was found by Cheapflights users on 9/30. 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 12/65:10 am -
1 stop8h 35m
Wed 12/93:25 pm -
1 stop6h 55m
Deal found 9/30![Southwest logo]()
$412
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Sat 10/246:47 pm -
2 stops16h 26m
Sat 10/312:01 pm -
1 stop8h 14m
Deal found 10/1![United Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 9/30. 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.
Sat 12/53:50 pm -
2 stops19h 37m
Wed 12/96:12 pm -
1 stop16h 01m
Deal found 9/30![Delta logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/30. 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 12/55:00 am -
1 stop9h 07m
Sat 12/124:07 pm -
1 stop16h 51m
Deal found 9/30![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 10/305:47 pm -
1 stop22h 25m
Fri 11/62:12 pm -
1 stop9h 43m
Deal found 9/29![American Airlines logo]()
$420
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 October 4, 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 October 4, 2026.
This United Airlines deal was found by Cheapflights users on 10/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:48 am -
2 stops9h 34m
Sat 10/312:05 am -
1 stop10h 18m
Deal found 10/3![United Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 9/30. 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.
Sat 10/241:05 pm -
2 stops9h 50m
Sun 11/16:35 am -
1 stop7h 30m
Deal found 9/30![Southwest logo]()
$386
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Fri 10/305:47 pm -
2 stops17h 31m
Fri 11/63:28 pm -
1 stop9h 28m
Deal found 10/2![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 10/1. 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 11/155:20 am -
1 stop7h 20m
Sun 11/224:05 pm -
1 stop9h 49m
Deal found 10/1![Delta logo]()
$537
This Southwest deal was found by Cheapflights users on 10/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/227:55 pm -
1 stop13h 30m
Sat 2/276:10 am -
1 stop13h 40m
Deal found 10/3![Southwest logo]()
$386
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 12/66:00 am -
1 stop6h 48m
Wed 12/92:54 pm -
1 stop8h 01m
Deal found 9/30![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 1/267:36 am -
1 stop6h 42m
Tue 2/93:35 pm -
2 stops18h 34m
Deal found 9/29![American Airlines logo]()
$418
This Southwest deal was found by Cheapflights users on 9/30. 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 12/610:20 am -
1 stop8h 25m
Fri 12/1112:40 pm -
1 stop8h 35m
Deal found 9/30![Southwest logo]()
$386
This United Airlines deal was found by Cheapflights users on 9/29. 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 10/246:38 pm -
1 stop16h 35m
Fri 10/3012:25 pm -
1 stop10h 39m
Deal found 9/29![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/29. 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 12/55:50 pm -
2 stops19h 55m
Sat 12/128:15 am -
2 stops15h 54m
Deal found 9/29![American Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 12/42:15 pm -
2 stops8h 30m
Tue 12/87:40 am -
2 stops10h 20m
Deal found 10/4![Southwest logo]()
$415
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Mon 12/77:09 am -
1 stop6h 15m
Mon 12/141:00 pm -
1 stop11h 09m
Deal found 9/29![American Airlines logo]()
$435
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 1/2110:35 am -
2 stops9h 47m
Sat 1/307:40 am -
2 stops11h 51m
Deal found 10/2![United Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 10/1. 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.
Sat 10/315:30 am -
1 stop7h 10m
Sat 11/74:05 pm -
1 stop9h 48m
Deal found 10/1![Delta logo]()
$537
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 12/167:20 pm -
1 stop13h 10m
Sun 12/2010:30 pm -
1 stop12h 45m
Deal found 10/4![Southwest logo]()
$449
This Delta deal was found by Cheapflights users on 10/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:30 am -
1 stop6h 10m
Fri 10/3012:55 pm -
1 stop10h 58m
Deal found 10/3![Delta logo]()
$570
This American Airlines deal was found by Cheapflights users on 10/2. 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 1/165:50 pm -
1 stop22h 13m
Wed 1/204:18 pm -
1 stop17h 05m
Deal found 10/2![American Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 10/2. 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 12/57:18 pm -
1 stop17h 30m
Tue 12/82:54 pm -
1 stop9h 01m
Deal found 10/2![United Airlines logo]()
$474
This Delta deal was found by Cheapflights users on 9/29. 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 11/35:30 am -
1 stop5h 20m
Sat 11/71:15 pm -
1 stop11h 38m
Deal found 9/29![Delta logo]()
$578
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 11/156:47 am -
1 stop6h 01m
Sun 11/222:54 pm -
1 stop18h 41m
Deal found 9/30![United Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:10 am -
1 stop7h 50m
Mon 11/233:45 pm -
1 stop9h 50m
Deal found 10/2![Southwest logo]()
$482
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 11/277:33 pm -
1 stop17h 26m
Mon 12/74:38 pm -
1 stop8h 31m
Deal found 10/1![American Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 10/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/112:45 pm -
1 stop8h 01m
Sun 1/106:10 pm -
1 stop16h 12m
Deal found 10/3![Delta logo]()
$586
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:20 am -
2 stops11h 00m
Sun 12/136:35 am -
1 stop12h 40m
Deal found 10/2![Southwest logo]()
$495
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Sat 1/165:50 pm -
2 stops20h 25m
Wed 1/208:25 am -
1 stop16h 15m
Deal found 10/1![American Airlines logo]()
$498
This United Airlines deal was found by Cheapflights users on 10/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:38 pm -
2 stops20h 11m
Sun 12/132:40 pm -
1 stop9h 12m
Deal found 10/3![United Airlines logo]()
$506
This Delta deal was found by Cheapflights users on 10/1. 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.
Wed 2/176:00 am -
1 stop8h 15m
Tue 2/236:10 pm -
1 stop6h 39m
Deal found 10/1![Delta logo]()
$586
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Sat 10/246:02 pm -
2 stops16h 58m
Fri 10/3012:25 pm -
1 stop11h 32m
Deal found 10/1![American Airlines logo]()
$498
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 1/179:20 am -
2 stops11h 02m
Sat 1/232:05 am -
1 stop9h 41m
Deal found 9/30![United Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 10/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3012:45 pm -
1 stop8h 01m
Sat 1/91:15 pm -
1 stop10h 14m
Deal found 10/3![Delta logo]()
$586
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated October 4, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated October 4, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:15 am -
1 stop14h 38m
Mon 10/193:00 am -
1 stop7h 20m
Deal found 9/30![Frontier logo]()
$306
This Frontier deal was found by Cheapflights users on 9/29. 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.
Thu 10/1510:15 am -
1 stop11h 50m
Mon 10/262:58 am -
1 stop7h 18m
Deal found 9/29![Frontier logo]()
$349
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop27h 21m
Mon 10/197:44 pm -
1 stop14h 36m
Deal found 9/29![Frontier logo]()
$359
This Frontier deal was found by Cheapflights users on 9/29. 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.
Thu 10/1510:15 am -
1 stop11h 50m
Wed 10/282:55 am -
1 stop7h 21m
Deal found 9/29![Frontier logo]()
$379
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Fri 10/237:19 pm -
2 stops18h 08m
Tue 10/275:13 pm -
2 stops21h 11m
Deal found 10/2![American Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 9/29. 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 10/246:38 pm -
1 stop16h 35m
Thu 10/292:20 pm -
1 stop8h 44m
Deal found 9/29![United Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Sat 10/246:47 pm -
2 stops16h 26m
Sat 10/312:01 pm -
1 stop8h 14m
Deal found 10/1![United Airlines logo]()
$413
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop14h 35m
Mon 11/211:20 am -
1 stop23h 56m
Deal found 9/30![Frontier logo]()
$305
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 10/305:47 pm -
1 stop22h 25m
Fri 11/62:12 pm -
1 stop9h 43m
Deal found 9/29![American Airlines logo]()
$420
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:15 am -
1 stop14h 35m
Mon 11/97:26 pm -
1 stop15h 50m
Deal found 9/29![Frontier logo]()
$255
This American Airlines deal was found by Cheapflights users on 10/1. 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 11/117:29 pm -
2 stops17h 59m
Tue 11/176:09 pm -
2 stops18h 39m
Deal found 10/1![American Airlines logo]()
$422
This FlightHub deal was found by Cheapflights users on 10/1. 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.
Thu 11/1210:15 am -
1 stop14h 35m
Sat 11/143:55 am -
1 stop7h 21m
Deal found 10/1![Frontier logo]()
$291
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 October 4, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
This Priceline deal was found by Cheapflights users on 9/29. 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.
Tue 10/2010:15 am -
1 stop14h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:15 am -
1 stop14h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$128
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop22h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$162
This American Airlines deal was found by Cheapflights users on 9/30. 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 1/303:34 pm -
2 stops19h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$182
This United Airlines deal was found by Cheapflights users on 10/2. 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 1/233:51 pm -
2 stops12h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![United Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/212:58 pm -
2 stops17h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$198
This American Airlines deal was found by Cheapflights users on 10/1. 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 11/306:25 pm -
2 stops14h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 9/30. 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.
Tue 1/195:35 am -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 10/1. 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.
Fri 11/137:40 pm -
2 stops16h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Southwest logo]()
$235
This United Airlines deal was found by Cheapflights users on 9/29. 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 1/95:00 am -
2 stops10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![United Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 10/1. 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 12/315:00 am -
2 stops10h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![United Airlines logo]()
$239
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 11/137:00 am -
1 stop5h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$239
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 October 4, 2026.
Round-trip from | $255 (Cheapflightsfares) |
|---|---|
One-way from | $105 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $399 |
Good round-trip deal | $425 or less |
Good one-way deal | $375 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 7,457,451 searches. Data last updated October 4, 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
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/30
6:40 am-5:03 pm
1 stop9h 23m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 11/1
5:10 am-12:50 pm
1 stop6h 40m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 11/1
2:55 pm-10:15 am
2 stops18h 20m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Fri 10/30
9:18 am-9:22 pm
2 stops11h 04m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Tue 12/8
7:45 am-4:54 pm
1 stop7h 09m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Mon 12/14
7:20 pm-9:55 am
1 stop12h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Wed 11/18
9:17 am-12:36 am
2 stops13h 19m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 1/23
7:36 am-9:11 pm
2 stops11h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sat 10/24
7:55 am-8:10 pm
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Thu 10/29
8:35 am-9:22 pm
2 stops11h 47m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
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-MBJ
MKE-SJU
MKE-PUJ
MKE-STT
MKE-PLS
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-MBJ
MKE-SJU
MKE-PUJ
MKE-STT
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $477). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $747). 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 October 4, 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.
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
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 October 4, 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 7,457,451 searches. Data last updated October 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$341 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$596 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$602 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$643 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$273 | Average$539 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$322 | Average$719 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$488 | Average$839 | FlexibilityNo cancel fee | On-time83% |