$99+ Cheap flights from Caribbean to Michigan
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — DTW
Jun 3 — Jun 101
Round-trip
1 adult, Economy
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Find cheap flights from Caribbean to Michigan with Cheapflights
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Cheapest flights from Caribbean to MichiganExplore the most affordable flight options available from Caribbean to Michigan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.
Explore the most affordable flight options available from Caribbean to Michigan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/29![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sun 5/3112:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/1![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
SJU
- ORD
1 stop7h 25m
Frontier
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/2![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 5/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/24:05 pm
SJU
- ORD
1 stop8h 00m
Frontier
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/2![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sun 5/2412:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/30![Frontier logo]()
$183
This eDestinos deal was found by Cheapflights users on 4/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/30![Frontier logo]()
$189
This eDestinos deal was found by Cheapflights users on 4/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:15 pm
SJU
- DTW
1 stop7h 24m
Frontier
Sun 6/76:57 pm
DTW
- SJU
1 stop29h 02m
Frontier
Deal found 4/29![Frontier logo]()
$192
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1511:00 am
SJU
- ORD
1 stop13h 59m
Frontier
Sun 5/1710:22 am
ORD
- SJU
1 stop12h 35m
Frontier
Deal found 5/1![Frontier logo]()
$196
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:59 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Thu 5/1410:22 am
ORD
- SJU
1 stop12h 35m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$198
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/1![Frontier logo]()
$201
This Travelocity deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:01 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$202
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:15 pm
SJU
- DTW
1 stop7h 24m
Frontier
Tue 5/1912:54 pm
DTW
- SJU
1 stop13h 14m
Frontier
Deal found 4/30![Frontier logo]()
$204
Best flights from Caribbean to MichiganDiscover carefully curated flight deals from Caribbean to Michigan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 4, 2026.
Discover carefully curated flight deals from Caribbean to Michigan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 4, 2026.
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 8/261:45 pm
SJU
- MDW
1 stop6h 30m
Southwest
Sun 8/305:00 am
MDW
- SJU
1 stop7h 00m
Southwest
Deal found 4/30![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 5/3. 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 8/52:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Tue 8/186:05 am
MDW
- SJU
1 stop9h 32m
Delta
Deal found 5/3![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Sun 5/108:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Deal found 4/28![United Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/295:17 pm
MBJ
- ORD
1 stop7h 07m
American Airlines
Wed 9/29:10 am
ORD
- MBJ
Nonstop4h 07m
American Airlines
Deal found 5/2![American Airlines logo]()
$317
This Arajet deal was found by Cheapflights users on 5/1. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 10/3111:27 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 5/1![Arajet logo]()
$359
This CheapOair deal was found by Cheapflights users on 5/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:15 pm
SJU
- DTW
1 stop7h 23m
Multiple Airlines
Mon 6/86:10 am
DTW
- SJU
1 stop16h 43m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$367
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:42 am
PUJ
- MDW
2 stops11h 29m
Frontier
Tue 9/16:00 am
MDW
- PUJ
1 stop7h 29m
Frontier
Deal found 5/1![Frontier logo]()
$475
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/194:33 pm
MBJ
- ORD
1 stop8h 12m
United Airlines
Fri 7/249:40 pm
ORD
- MBJ
1 stop17h 46m
United Airlines
Deal found 4/28![United Airlines logo]()
$296
This Copa Airlines deal was found by Cheapflights users on 5/3. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:16 pm
SDQ
- ORD
1 stop11h 46m
Copa Airlines
Sun 9/278:01 am
ORD
- SDQ
1 stop25h 54m
Copa Airlines
Deal found 5/3![Copa Airlines logo]()
$592
This JetBlue deal was found by Cheapflights users on 5/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/223:10 am
SDQ
- ORD
1 stop10h 51m
JetBlue
Wed 5/273:27 pm
ORD
- SDQ
1 stop7h 53m
JetBlue
Deal found 5/3![JetBlue logo]()
$605
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/234:33 pm
MBJ
- ORD
1 stop17h 47m
United Airlines
Sat 5/308:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Deal found 4/29![United Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:00 am
SJU
- MDW
1 stop9h 00m
Southwest
Wed 8/1912:20 pm
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 4/29![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 6/24:12 pm
MBJ
- ORD
1 stop15h 15m
United Airlines
Fri 6/59:40 pm
ORD
- MBJ
1 stop17h 30m
United Airlines
Deal found 4/29![United Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 7/297:00 am
SJU
- MDW
1 stop6h 45m
Southwest
Tue 8/47:30 am
MDW
- SJU
1 stop10h 30m
Southwest
Deal found 4/30![Southwest logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:00 am
SJU
- GRR
1 stop12h 00m
Multiple Airlines
Sat 6/138:29 pm
GRR
- SJU
2 stops28h 08m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Thu 5/72:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 4/29![United Airlines logo]()
$309
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:31 pm
SJU
- ORD
1 stop29h 34m
Multiple Airlines
Thu 7/168:41 pm
ORD
- SJU
2 stops23h 10m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$374
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/2912:44 am
SJU
- GRR
1 stop11h 38m
American Airlines
Tue 6/163:23 pm
GRR
- SJU
1 stop7h 37m
American Airlines
Deal found 4/29![American Airlines logo]()
$415
This Arajet deal was found by Cheapflights users on 4/30. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 8/2212:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/30![Arajet logo]()
$425
This Southwest deal was found by Cheapflights users on 5/2. 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.
Fri 9/1810:00 am
SJU
- MDW
1 stop9h 00m
Southwest
Mon 9/212:55 pm
MDW
- SJU
1 stop7h 55m
Southwest
Deal found 5/2![Southwest logo]()
$366
This United Airlines deal was found by Cheapflights users on 5/2. 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 5/232:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Thu 7/239:40 pm
ORD
- MBJ
1 stop17h 30m
United Airlines
Deal found 5/2![United Airlines logo]()
$312
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:35 pm
PUJ
- ORD
1 stop17h 20m
Multiple Airlines
Sun 5/178:35 pm
ORD
- PUJ
1 stop14h 20m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$380
This CheapOair deal was found by Cheapflights users on 5/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:29 pm
PUJ
- MDW
2 stops49h 39m
Frontier
Sat 8/2211:59 am
MDW
- PUJ
1 stop25h 30m
Frontier
Deal found 5/2![Frontier logo]()
$487
This Delta deal was found by Cheapflights users on 4/29. 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 7/71:16 pm
NAS
- ORD
1 stop6h 29m
Delta
Sun 7/125:30 am
ORD
- NAS
1 stop7h 31m
Delta
Deal found 4/29![Delta logo]()
$491
This KAYAK deal was found by Cheapflights users on 5/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:25 am
SJU
- ORD
1 stop17h 29m
American Airlines
Tue 5/1212:45 pm
ORD
- SJU
1 stop8h 20m
American Airlines
Deal found 5/1![American Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Tue 6/24:12 pm
MBJ
- ORD
1 stop15h 15m
United Airlines
Sat 6/206:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Deal found 5/1![United Airlines logo]()
$312
This Arajet deal was found by Cheapflights users on 4/29. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:45 pm
SDQ
- ORD
1 stop10h 55m
Multiple Airlines
Mon 10/195:30 am
ORD
- SDQ
1 stop10h 25m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 5/2. 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 6/116:00 am
SJU
- MDW
1 stop9h 40m
Southwest
Mon 6/1511:35 am
MDW
- SJU
1 stop11h 50m
Southwest
Deal found 5/2![Southwest logo]()
$391
This Arajet deal was found by Cheapflights users on 4/29. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 11/710:27 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/29![Arajet logo]()
$483
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/151:16 pm
NAS
- ORD
2 stops8h 15m
Delta
Mon 7/206:35 am
ORD
- NAS
1 stop6h 26m
Delta
Deal found 4/29![Delta logo]()
$491
Last-minute flights from Caribbean to MichiganDiscover last-minute flight deals from Caribbean to Michigan. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Michigan. Data last updated May 4, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Fri 5/157:30 am
ORD
- SJU
1 stop14h 58m
Frontier
Deal found 5/1![Frontier logo]()
$205
This CheapOair deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:59 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Sat 5/165:30 pm
ORD
- SJU
1 stop13h 34m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$203
This Orbitz deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:59 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Thu 5/143:44 pm
ORD
- SJU
1 stop24h 32m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sat 5/94:59 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Fri 5/2912:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$225
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:33 pm
SJU
- ORD
1 stop8h 40m
Frontier
Fri 5/2912:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/29![Frontier logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Sat 5/94:59 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sat 5/1612:59 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$228
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/123:03 am
SJU
- ORD
1 stop21h 10m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/29![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:15 pm
SJU
- DTW
1 stop7h 24m
Frontier
Tue 5/1912:54 pm
DTW
- SJU
1 stop13h 14m
Frontier
Deal found 4/30![Frontier logo]()
$204
This Expedia deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:15 pm
SJU
- DTW
1 stop7h 24m
Frontier
Wed 5/2712:44 pm
DTW
- SJU
1 stop13h 24m
Frontier
Deal found 5/1![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 4/29. 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.
Wed 5/275:15 pm
SJU
- DTW
1 stop7h 24m
Frontier
Fri 6/512:44 pm
DTW
- SJU
1 stop10h 38m
Frontier
Deal found 4/29![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:15 pm
SJU
- DTW
1 stop7h 24m
Frontier
Tue 8/1112:37 pm
DTW
- SJU
1 stop13h 34m
Frontier
Deal found 4/30![Frontier logo]()
$224
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:15 pm
SJU
- DTW
1 stop7h 24m
Frontier
Sat 8/87:58 pm
DTW
- SJU
1 stop9h 04m
Frontier
Deal found 4/30![Frontier logo]()
$226
One-way flights from Caribbean to MichiganSearch for one-way flight options from Caribbean to Michigan. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
Search for one-way flight options from Caribbean to Michigan. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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.
Sat 5/234:59 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$99
This Spirit deal was found by Cheapflights users on 4/30. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$100
This Trip.com deal was found by Cheapflights users on 5/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/2![Frontier logo]()
$101
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:25 am
SJU
- MDW
1 stop8h 47m
Frontier
Deal found 4/30![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 4/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:03 am
SJU
- ORD
1 stop21h 10m
Frontier
Deal found 4/29![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/2911:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$105
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/1![Frontier logo]()
$108
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/2312:59 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 4/30![American Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:00 am
SJU
- ORD
1 stop7h 24m
Frontier
Deal found 4/30![Frontier logo]()
$110
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:59 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 5/1![American Airlines logo]()
$111
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 5/1![Frontier logo]()
$112
This Southwest deal was found by Cheapflights users on 5/2. 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 9/35:30 am
SJU
- MDW
2 stops10h 25m
Southwest
Deal found 5/2![Southwest logo]()
$113
Find flight deals from Caribbean to Michigan
Keep the following information in mind while searching for Caribbean to Michigan flight deals. Data was last updated May 4, 2026.
Round-trip from | $165 (Priceline) |
|---|---|
One-way from | $99 (Cheapflightsfares) |
Popular in | March |
Cheapest in | November |
Average price | $374 |
Good round-trip deal | $482 or less |
Good one-way deal | $197 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to Michigan 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 May 4, 2026.
Use the filters below to find and compare flights from Caribbean to Michigan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/26
1:45 pm-7:15 pm
1 stop6h 30m
Chicago Midway
Sun 8/30
5:00 am-1:00 pm
1 stop7h 00m
$226
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/5
2:59 pm-10:36 pm
1 stop8h 37m
Chicago Midway
Tue 8/18
6:05 am-4:37 pm
1 stop9h 32m
$256
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 5/7
3:56 pm-8:15 pm
Nonstop5h 19m
Chicago O'Hare Intl
Sun 5/10
8:49 am-2:44 pm
Nonstop4h 55m
$257
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sun 7/19
4:33 pm-12:45 am
1 stop8h 12m
Chicago O'Hare Intl
Fri 7/24
9:40 pm-3:26 pm
1 stop17h 46m
$296
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sat 5/23
4:33 pm-10:20 am
1 stop17h 47m
Chicago O'Hare Intl
Sat 5/30
8:40 am-3:10 pm
1 stop6h 30m
$296
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Tue 6/2
4:12 pm-7:27 am
1 stop15h 15m
Chicago O'Hare Intl
Fri 6/5
9:40 pm-3:10 pm
1 stop17h 30m
$296
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 5/6
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Thu 5/7
2:38 pm-8:34 pm
Nonstop4h 56m
$309
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sat 5/23
2:40 pm-12:45 am
1 stop10h 05m
Chicago O'Hare Intl
Thu 7/23
9:40 pm-3:10 pm
1 stop17h 30m
$312
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Tue 6/2
4:12 pm-7:27 am
1 stop15h 15m
Chicago O'Hare Intl
Sat 6/20
6:30 am-3:10 pm
1 stop8h 40m
$312
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Fri 5/29
5:17 pm-12:24 am
1 stop7h 07m
Chicago O'Hare Intl
Wed 9/2
9:10 am-1:17 pm
Nonstop4h 07m
$317
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Caribbean to Michigan
Have a flexible travel schedule? Discover the best time to fly to Michigan from Caribbean with our price prediction graph.
SJU-MDW
SJU-ORD
SJU-GRR
PUJ-ORD
NAS-ORD
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 Caribbean to Michigan
0CB-USMI
SJU-MDW
SJU-ORD
SJU-GRR
PUJ-ORD
How far ahead should I book a flight from Caribbean to Michigan?
To ensure you get the cheapest price possible for a flight from Caribbean to Michigan, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Caribbean to Michigan?
Currently, October is the cheapest month in which you can book a flight from Caribbean to Michigan (average of $72). Flying from Caribbean to Michigan in March is currently the most expensive (average of $256). 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 CB to MI?
Find hourly flight availability from Caribbean to Michigan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 4, 2026.
One of the essential ways to save on airfare from Caribbean to Michigan is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 36% on airfare.
Reviews of airlines servicing Michigan
Get insights into the airlines that provide service to Michigan. 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 Michigan. Reviews last updated May 4, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from Caribbean to Michigan by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreBarney,May 2026
JFK - ATL
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Michigan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Return Flight Options
Top destinations
Alternative routes for Caribbean to Michigan
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Michigan by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to Michigan by cabin class
Find flights from Caribbean to Michigan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean and Michigan flights
Browse other Caribbean and Michigan flight options. Last updated on May 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Michigan
Find the right flight back to Caribbean after your stay in Michigan
Caribbean to Michigan flights
Consider these flights traveling from Caribbean to Michigan.
Top 5 airlines flying from Caribbean to Michigan
Discover the top 5 airlines that operate flights from Caribbean to Michigan. 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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$89 | Average$275 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$102 | Average$334 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$190 | Average$550 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$655 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$554 | Average$580 | FlexibilityNo cancel fee | On-time69% |