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$81+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This Priceline deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:00 amORD - SJU
1 stop9h 53mMultiple Airlines
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/10$201
This Frontier deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - SJU
1 stop7h 04mFrontier
Thu 1/154:35 pmSJU - ORD
1 stop8h 09mFrontier
Deal found 12/11$205
This Trip.com deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/137:00 amORD - SJU
1 stop9h 53mMultiple Airlines
Thu 12/185:09 pmSJU - ORD
1 stop17h 43mMultiple Airlines
Deal found 12/10$206
This WAYA deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - SJU
1 stop8h 35mMultiple Airlines
Fri 1/95:18 pmSJU - ORD
1 stop8h 28mMultiple Airlines
Deal found 12/10$208
This Expedia deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/157:49 amDTW - SJU
1 stop15h 56mMultiple Airlines
Thu 12/189:37 pmSJU - DTW
1 stop12h 16mMultiple Airlines
Deal found 12/10$209
This CheapOair deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/137:42 pmDTW - SJU
1 stop13h 51mSpirit Airlines
Sun 12/2111:38 amSJU - DTW
1 stop6h 57mSpirit Airlines
Deal found 12/10$212
This Trip.com deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/137:00 amORD - SJU
1 stop9h 53mJetBlue
Mon 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/11$215
This Booking.com deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:58 pmDTW - SJU
1 stop16h 34mMultiple Airlines
Fri 12/191:59 amSJU - DTW
1 stop14h 48mMultiple Airlines
Deal found 12/10$216
This Cheapflightsfares deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/157:49 amDTW - SJU
1 stop15h 56mSpirit Airlines
Tue 12/2311:38 amSJU - DTW
1 stop10h 54mSpirit Airlines
Deal found 12/11$218
This Super.com deal was found by Cheapflights users on 12/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:58 pmDTW - SJU
1 stop16h 34mSpirit Airlines
Sun 12/2112:53 pmSJU - DTW
1 stop12h 49mSpirit Airlines
Deal found 12/9$219
This Trip.com deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/127:00 amORD - SJU
1 stop9h 52mJetBlue
Mon 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/10$220
This Expedia deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:58 pmDTW - SJU
1 stop16h 34mSpirit Airlines
Thu 12/184:10 amSJU - DTW
1 stop6h 23mSpirit Airlines
Deal found 12/9$220

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 December 12, 2025.

Round-trip from

$199
(Priceline)

One-way from

$81
(Cheapflightsfares)

Popular in

December

Cheapest in

October

Average price

$594

Good round-trip deal

$410 or less

Good one-way deal

$112 or less
From Michigan to Caribbean
Search Deals
One-way flight from Michigan to Caribbean
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($97 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Michigan to Caribbean.
Search Deals
Price to beat on a one-way 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 December 12, 2025.
Use the filters below to find and compare flights from Michigan to Caribbean that are best for you.

Fly from

Michigan

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/28

8:00 am-2:53 am

1 stop16h 53m

San Juan Luis Munoz Marin Intl

Sat 3/7

12:07 pm-11:32 pm

1 stop13h 25m

$201

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Sat 3/7

5:10 am-11:58 am

1 stop8h 48m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 6/2

3:15 pm-1:59 am

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Tue 6/9

12:30 pm-7:26 pm

1 stop7h 56m

$214

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 2/6

1:00 pm-3:26 pm

1 stop24h 26m

San Juan Luis Munoz Marin Intl

Sat 2/14

8:02 pm-2:26 pm

1 stop20h 24m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Sun 3/1

5:10 am-11:48 am

1 stop8h 38m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/31

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Mon 2/2

11:06 am-7:36 pm

1 stop10h 30m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 3/11

12:41 pm-9:31 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Thu 3/19

1:30 am-10:05 am

1 stop9h 35m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 3/20

10:56 am-11:23 pm

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Tue 3/24

1:30 am-10:05 am

1 stop9h 35m

$220

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

3:15 pm-12:40 am

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-11:35 am

1 stop7h 25m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 60 results
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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, August is the cheapest month in which you can book a flight from Michigan to Caribbean (average of $132). Flying from Michigan to Caribbean in April is currently the most expensive (average of $212). 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 December 12, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 20% on flights from Michigan to Caribbean by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Michigan to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Michigan to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Michigan to Caribbean flight should consider departing on Saturday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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?

    Frontier, JetBlue, and Southwest can get you from Michigan to Caribbean in just under 7h 25m. Your travel time can differ by up to 9h 28m. The distance between Michigan and Caribbean is about 2057 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 $62. However, be on the lookout for offers from Spirit Airlines and United 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, August is the cheapest month in which you can book a flight from Michigan to Caribbean (average of $132). Flying from Michigan to Caribbean in April is currently the most expensive (average of $212). 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

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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 8 airlines flying from Michigan to Caribbean

Discover the top 8 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$392FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$148Average$417FlexibilityNo cancel feeOn-time65%
DeltaCheapest$232Average$701FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$235Average$678FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$264Average$678FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$266Average$513FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$268Average$517FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$354Average$733FlexibilityNo cancel feeOn-time63%

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