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Caribbean

$94+ Cheap flights from Michigan to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — SJU
Jul 19 — Jul 261
Sun 7/19
Sun 7/26
1 adult, Economy
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Cheap flight deals from Michigan to Caribbean

Cheapest flights from Michigan to Caribbean
Explore the most affordable flight options available from Michigan to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.

This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/316:29 pm
ORD
-
SJU
1 stop10h 00m
United Airlines
Fri 8/283:56 pm
SJU
-
ORD
Nonstop5h 09m
United Airlines
Deal found 6/14$254
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/226:40 am
ORD
-
SJU
1 stop8h 58m
Delta
Mon 8/317:00 am
SJU
-
ORD
1 stop8h 09m
Delta
Deal found 6/16$256
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/227:50 am
MDW
-
SJU
2 stops7h 50m
Southwest
Wed 8/2610:30 am
SJU
-
MDW
1 stop8h 10m
Southwest
Deal found 6/16$256
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:20 pm
ORD
-
SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
-
ORD
1 stop11h 57m
American Airlines
Deal found 6/15$257
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Fri 8/216:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 6/15$258
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/1512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/226:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 6/15$260
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/154:59 pm
ORD
-
SJU
Nonstop4h 55m
American Airlines
Sat 8/227:20 pm
SJU
-
ORD
1 stop13h 14m
American Airlines
Deal found 6/18$262
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/1912:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Mon 8/246:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 6/16$263
This eDestinos deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Mon 7/612:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Tue 7/147:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 6/18$264
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/1712:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Sat 8/226:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 6/15$265
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/95:30 am
ORD
-
SJU
1 stop10h 08m
Delta
Thu 8/132:59 pm
SJU
-
ORD
1 stop9h 58m
Delta
Deal found 6/17$266
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/2911:00 am
MDW
-
SJU
1 stop6h 15m
Southwest
Sat 9/55:55 am
SJU
-
MDW
1 stop11h 45m
Southwest
Deal found 6/16$266

Find flight deals from Michigan to Caribbean

Keep the following information in mind while searching for Michigan to Caribbean flight deals. Data was last updated June 19, 2026.

Round-trip from

$254
(United Airlines)

One-way from

$94
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$495

Good round-trip deal

$637 or less
From Michigan to Caribbean
Search Deals
One-way flight from Michigan to Caribbean
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Michigan to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Michigan to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 19, 2026.
Use the filters below to find and compare flights from Michigan to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/18

12:46 pm-10:29 pm

1 stop8h 43m

San Juan Luis Munoz Marin Intl

Mon 8/31

7:00 am-3:44 pm

1 stop9h 44m

$266

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/8

8:02 pm-5:29 am

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Wed 8/12

1:25 pm-10:15 pm

1 stop9h 50m

$318

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/20

1:00 pm-10:50 pm

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Mon 8/24

6:00 am-2:30 pm

2 stops9h 30m

$326

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/24

6:30 am-3:42 pm

1 stop8h 12m

San Juan Luis Munoz Marin Intl

Wed 8/26

4:55 pm-11:40 pm

1 stop7h 45m

$336

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Sat 7/18

7:00 am-5:22 pm

1 stop9h 22m

Nassau Intl

Wed 7/22

12:20 pm-11:44 pm

1 stop12h 24m

$344

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/15

7:50 am-6:05 pm

2 stops9h 15m

San Juan Luis Munoz Marin Intl

Sun 8/23

6:35 am-3:50 pm

2 stops10h 15m

$351

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Sat 7/25

7:00 am-5:22 pm

1 stop9h 22m

Nassau Intl

Fri 7/31

3:02 pm-11:44 pm

1 stop9h 42m

$363

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 8/7

8:02 pm-5:29 am

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Tue 8/11

7:20 am-2:30 pm

1 stop8h 10m

$376

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/13

3:10 pm-11:50 pm

2 stops7h 40m

San Juan Luis Munoz Marin Intl

Wed 8/19

5:15 am-12:05 pm

2 stops7h 50m

$376

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 8/16

3:00 pm-12:30 am

2 stops8h 30m

San Juan Luis Munoz Marin Intl

Wed 8/19

5:15 am-12:05 pm

2 stops7h 50m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Michigan to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Michigan with our price prediction graph.
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 Michigan to Caribbean

What is the cheapest month to book a flight from Michigan to Caribbean?

Currently, January is the cheapest month in which you can book a flight from Michigan to Caribbean (average of $523). Flying from Michigan to Caribbean in December is currently the most expensive (average of $797). 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 MI to CB?

Find hourly flight availability from Michigan to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 19, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Michigan to Caribbean as you normally would.

Weekly flight availability from Michigan to Caribbean

Explore weekly flight availability from Michigan to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 19, 2026.

The most flights from USMI to 0CB are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

How far ahead should I book a flight from Michigan to Caribbean?

To ensure you get the cheapest price possible for a flight from Michigan to Caribbean, you should look to book at least 10 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.

Related info for your journey

Find useful and relevant information for your journey from Michigan to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Michigan to Caribbean?

    Delta, United Airlines, and Southwest can get you from Michigan to Caribbean in just under 8h 27m. Your travel time can differ by up to 23m. The distance between Michigan and Caribbean is about 2073 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Michigan to Caribbean one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $84. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Michigan to Caribbean for a low price.

  • Can I find deals for flights from Michigan to Caribbean that include hotel bookings?

    Yes. In addition to deals on Michigan to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Michigan to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Michigan to Caribbean.

  • Can I find deals for business class flights from Michigan to Caribbean?

    Yes. Cheapflights offers flight deals from Michigan to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Michigan to Caribbean?

    Currently, January is the cheapest month in which you can book a flight from Michigan to Caribbean (average of $523). Flying from Michigan to Caribbean in December is currently the most expensive (average of $797). 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.

See more FAQs

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 for Michigan to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Michigan to Caribbean

Discover the top 7 airlines that operate flights from Michigan to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$387FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$180Average$548FlexibilityNo cancel feeOn-time62%
DeltaCheapest$196Average$732FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$225Average$620FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$235Average$684FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$265Average$451FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$342Average$682FlexibilityNo cancel feeOn-time63%

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