$100+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 8 — Nov 151
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 9, 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 9, 2026.
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 10/296:27 pm -
1 stop15h 53m
Mon 11/28:30 am -
1 stop13h 45m
Deal found 10/6![American Airlines logo]()
$262
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:20 am -
1 stop9h 55m
Sat 11/217:15 pm -
1 stop7h 05m
Deal found 10/8![Southwest logo]()
$282
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/285:10 pm -
2 stops17h 10m
Mon 11/22:44 pm -
1 stop7h 31m
Deal found 10/7![American Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:48 am -
2 stops9h 34m
Fri 11/132:05 am -
2 stops11h 23m
Deal found 10/6![United Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/119:17 am -
2 stops11h 05m
Sat 11/147:40 am -
1 stop9h 35m
Deal found 10/7![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:55 pm -
1 stop12h 05m
Tue 12/156:40 am -
1 stop7h 20m
Deal found 10/8![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/48:00 am -
2 stops11h 24m
Wed 11/113:46 pm -
1 stop9h 00m
Deal found 10/5![United Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/276:25 pm -
1 stop15h 31m
Sat 12/54:36 pm -
1 stop8h 33m
Deal found 10/5![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:48 am -
2 stops11h 48m
Tue 11/108:25 am -
1 stop7h 07m
Deal found 10/8![United Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:48 am -
1 stop8h 12m
Thu 11/198:25 am -
1 stop8h 33m
Deal found 10/6![United Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:33 pm -
2 stops16h 26m
Mon 12/74:38 pm -
2 stops17h 20m
Deal found 10/8![American Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:03 pm -
1 stop6h 57m
Fri 11/202:05 am -
2 stops11h 23m
Deal found 10/6![United Airlines logo]()
$348
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 9, 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 9, 2026.
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:55 pm -
1 stop12h 05m
Tue 12/156:40 am -
1 stop7h 20m
Deal found 10/8![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 2/216:00 am -
1 stop6h 48m
Fri 2/262:54 pm -
1 stop7h 13m
Deal found 10/6![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/145:20 am -
1 stop10h 37m
Fri 11/202:16 pm -
1 stop10h 38m
Deal found 10/7![Delta logo]()
$416
This American Airlines deal was found by Cheapflights users on 10/9. 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 12/82:51 pm -
2 stops18h 24m
Mon 12/146:09 pm -
2 stops18h 41m
Deal found 10/9![American Airlines logo]()
$417
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 12/91:25 pm -
2 stops19h 10m
Deal found 10/6![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:20 pm -
1 stop12h 35m
Thu 12/174:00 pm -
2 stops9h 05m
Deal found 10/8![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/199:20 am -
2 stops13h 16m
Tue 1/262:05 am -
1 stop10h 53m
Deal found 10/7![United Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 -
2 stops14h 01m
Sat 12/123:45 pm -
2 stops8h 24m
Deal found 10/6![American Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/2712:45 pm -
2 stops10h 15m
Sat 12/55:40 am -
2 stops10h 40m
Deal found 10/5![Southwest logo]()
$415
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2112:20 pm -
1 stop9h 30m
Thu 2/256:30 pm -
1 stop7h 19m
Deal found 10/4![Delta logo]()
$472
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:25 pm -
1 stop15h 58m
Thu 12/31:00 pm -
1 stop11h 55m
Deal found 10/8![American Airlines logo]()
$436
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/236:50 pm -
2 stops18h 24m
Sat 1/303:45 pm -
1 stop8h 00m
Deal found 10/4![United Airlines logo]()
$414
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/305:55 am -
1 stop8h 20m
Fri 2/53:10 pm -
1 stop7h 58m
Deal found 10/4![Delta logo]()
$482
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/225:00 am -
1 stop9h 20m
Fri 1/293:00 pm -
1 stop7h 59m
Deal found 10/6![United Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 3/37:00 am -
1 stop6h 25m
Tue 3/93:50 pm -
1 stop8h 59m
Deal found 10/6![Delta logo]()
$492
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:29 pm -
2 stops18h 34m
Thu 11/122:18 pm -
1 stop11h 38m
Deal found 10/8![American Airlines logo]()
$504
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 4/65:00 am -
1 stop7h 30m
Tue 4/132:30 pm -
1 stop9h 20m
Deal found 10/6![Southwest logo]()
$527
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/275:55 am -
1 stop8h 20m
Sun 2/71:50 pm -
1 stop11h 59m
Deal found 10/8![Delta logo]()
$500
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 11/35:08 pm -
2 stops17h 15m
Sat 11/73:45 pm -
2 stops17h 03m
Deal found 10/6![American Airlines logo]()
$512
This United Airlines deal was found by Cheapflights users on 10/9. 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 1/165:00 am -
2 stops10h 19m
Wed 1/202:54 pm -
1 stop7h 05m
Deal found 10/9![United Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 2/246:25 am -
2 stops10h 20m
Mon 3/17:35 am -
2 stops9h 25m
Deal found 10/5![Southwest logo]()
$530
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/315:55 am -
1 stop8h 20m
Mon 2/84:15 pm -
1 stop9h 34m
Deal found 10/8![Delta logo]()
$500
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/912:45 pm -
2 stops15h 30m
Sat 1/232:05 am -
2 stops15h 05m
Deal found 10/8![United Airlines logo]()
$473
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/285:00 am -
2 stops13h 50m
Tue 2/212:48 pm -
2 stops10h 48m
Deal found 10/4![American Airlines logo]()
$544
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 3/46:40 pm -
1 stop15h 30m
Tue 3/96:00 pm -
1 stop6h 49m
Deal found 10/5![Delta logo]()
$509
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 10/285:45 am -
1 stop6h 30m
Sun 11/11:10 pm -
1 stop11h 35m
Deal found 10/6![Southwest logo]()
$586
This American Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/72:55 pm -
2 stops21h 35m
Thu 11/125:25 pm -
1 stop8h 31m
Deal found 10/9![American Airlines logo]()
$552
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 2/15:00 am -
1 stop9h 20m
Wed 2/33:00 pm -
1 stop10h 15m
Deal found 10/5![United Airlines logo]()
$504
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:30 am -
1 stop7h 40m
Sun 11/18:15 am -
1 stop7h 39m
Deal found 10/8![Delta logo]()
$526
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.
Sun 11/298:10 pm -
2 stops15h 05m
Sat 12/51:55 pm -
2 stops8h 40m
Deal found 10/4![Southwest logo]()
$591
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated October 9, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/285:10 pm -
2 stops17h 10m
Mon 11/22:44 pm -
1 stop7h 31m
Deal found 10/7![American Airlines logo]()
$287
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 10/296:27 pm -
1 stop15h 53m
Mon 11/28:30 am -
1 stop13h 45m
Deal found 10/6![American Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:48 am -
2 stops9h 34m
Fri 11/132:05 am -
2 stops11h 23m
Deal found 10/6![United Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/48:00 am -
2 stops11h 24m
Wed 11/113:46 pm -
1 stop9h 00m
Deal found 10/5![United Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:20 am -
1 stop9h 55m
Sat 11/217:15 pm -
1 stop7h 05m
Deal found 10/8![Southwest logo]()
$282
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:48 am -
2 stops11h 48m
Tue 11/108:25 am -
1 stop7h 07m
Deal found 10/8![United Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/77:29 pm -
2 stops17h 59m
Wed 11/111:02 pm -
2 stops11h 53m
Deal found 10/5![American Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/119:17 am -
2 stops11h 05m
Sat 11/147:40 am -
1 stop9h 35m
Deal found 10/7![United Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:48 am -
2 stops9h 34m
Thu 11/198:05 am -
2 stops10h 58m
Deal found 10/6![United Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:03 pm -
1 stop6h 57m
Fri 11/202:05 am -
2 stops11h 23m
Deal found 10/6![United Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 -
2 stops18h 17m
Sat 12/54:36 pm -
1 stop8h 33m
Deal found 10/5![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:33 pm -
2 stops16h 26m
Mon 12/74:38 pm -
2 stops17h 20m
Deal found 10/8![American Airlines logo]()
$346
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 9, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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.
Mon 12/75:24 pm -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$100
This Priceline deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 10/2910:15 am -
1 stop14h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$102
This Priceline deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 10/2710:15 am -
1 stop22h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$108
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 10/288:00 am -
1 stop11h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![United Airlines logo]()
$131
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/156:31 pm -
2 stops13h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$136
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/285:00 am -
2 stops16h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$142
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” 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 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![American Airlines logo]()
$152
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/266:48 am -
2 stops8h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$155
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:19 pm -
2 stops17h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$158
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/286:18 pm -
2 stops20h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$161
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 1/235:00 am -
2 stops10h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$161
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:47 pm -
1 stop23h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$165
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 9, 2026.
Round-trip from | $262 (American Airlines) |
|---|---|
One-way from | $100 (Cheapflightsfares) |
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 9, 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 Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Sun 11/1
8:00 am-10:22 pm
2 stops12h 22m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$131
MilwaukeeSan Juan
MKE Milwaukee-Mitchell - SJU San Juan Luis Munoz Marin Intl
MKESJU
Milwaukee-Mitchell
Tue 12/8
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
$141
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 1/30
3:34 pm-12:03 pm
2 stops19h 29m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$152
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Tue 11/3
5:00 am-1:48 pm
1 stop7h 48m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$152
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Tue 10/27
6:47 am-12:48 pm
1 stop6h 01m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$152
MilwaukeeProvidenciales
MKE Milwaukee-Mitchell - PLS Providenciales
MKEPLS
Milwaukee-Mitchell
Mon 10/26
6:48 am-4:00 pm
2 stops8h 12m
Providenciales
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 11/1
7:29 pm-2:22 pm
2 stops17h 53m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
MilwaukeeSaint Thomas Island
MKE Milwaukee-Mitchell - STT Saint Thomas Island Cyril E King
MKESTT
Milwaukee-Mitchell
Sat 1/23
8:03 pm-3:10 pm
1 stop17h 07m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
MilwaukeeSaint Thomas Island
MKE Milwaukee-Mitchell - STT Saint Thomas Island Cyril E King
MKESTT
Milwaukee-Mitchell
Sat 1/30
5:00 am-2:31 pm
1 stop7h 31m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
MilwaukeeSaint Thomas Island
MKE Milwaukee-Mitchell - STT Saint Thomas Island Cyril E King
MKESTT
Milwaukee-Mitchell
Sat 1/23
5:00 am-5:50 pm
2 stops10h 50m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
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-STT
MKE-MBJ
MKE-PLS
MKE-PUJ
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-STT
MKE-MBJ
MKE-PLS
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 9, 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.
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
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 9, 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$341 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$600 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$599 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$642 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$273 | Average$548 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$322 | Average$719 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$488 | Average$828 | FlexibilityNo cancel fee | On-time83% |