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Caribbean Islands

$90+ Cheap flights from Midway (MDW) to Caribbean Islands

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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from Midway to Caribbean Islands

Keep the following information in mind while searching for Midway to Caribbean Islands flight deals. Data was last updated January 12, 2026.

Round-trip from

$198
(Frontier)

One-way from

$90
(Priceline)

Popular in

December

Cheapest in

April

Average price

$359
From Chicago Midway to Caribbean Islands
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One-way flight from Chicago Midway to Caribbean Islands
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Highest demand for flights based on searches. 10% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Midway to Caribbean Islands

Cheapest flights from Midway to Caribbean Islands
Explore the most affordable flight options available from Midway to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 12, 2026.

This Frontier deal was found by Cheapflights users on 1/11. 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.
Mon 3/99:51 pm
MDW
-
SJU
1 stop11h 06m
Frontier
Wed 3/116:30 am
SJU
-
MDW
1 stop12h 43m
Frontier
Deal found 1/11$198
This CheapOair deal was found by Cheapflights users on 1/12. 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.
Mon 3/99:51 pm
MDW
-
SJU
1 stop27h 12m
Frontier
Tue 3/173:22 pm
SJU
-
MDW
1 stop7h 57m
Frontier
Deal found 1/12$199
This Priceline deal was found by Cheapflights users on 1/12. 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.
Mon 2/97:00 pm
MDW
-
SJU
1 stop15h 57m
Frontier
Mon 3/91:01 pm
SJU
-
MDW
1 stop7h 46m
Frontier
Deal found 1/12$201
This Priceline deal was found by Cheapflights users on 1/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 am
MDW
-
SJU
1 stop8h 59m
Frontier
Thu 2/266:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
Deal found 1/11$203
This CheapOair deal was found by Cheapflights users on 1/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:00 pm
MDW
-
SJU
1 stop19h 24m
Frontier
Wed 2/115:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Deal found 1/11$204
This Priceline deal was found by Cheapflights users on 1/12. 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.
Fri 2/207:30 am
MDW
-
SJU
1 stop15h 13m
Frontier
Wed 2/255:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Deal found 1/12$205
This Priceline deal was found by Cheapflights users on 1/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:30 am
MDW
-
SJU
1 stop17h 23m
Frontier
Tue 3/246:30 am
SJU
-
MDW
1 stop12h 43m
Frontier
Deal found 1/11$206
This CheapOair deal was found by Cheapflights users on 1/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:30 am
MDW
-
SJU
1 stop15h 13m
Frontier
Fri 3/63:58 am
SJU
-
MDW
1 stop21h 34m
Frontier
Deal found 1/11$207
This Expedia deal was found by Cheapflights users on 1/10. 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.
Sun 2/226:00 am
MDW
-
SJU
1 stop7h 08m
Frontier
Thu 2/266:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
Deal found 1/10$209
This CheapOair deal was found by Cheapflights users on 1/12. 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.
Sun 2/227:30 am
MDW
-
SJU
1 stop15h 24m
Frontier
Wed 3/45:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Deal found 1/12$210
This Frontier deal was found by Cheapflights users on 1/12. 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.
Mon 3/169:51 pm
MDW
-
SJU
1 stop11h 06m
Frontier
Wed 3/183:22 pm
SJU
-
MDW
1 stop7h 57m
Frontier
Deal found 1/12$211
This Priceline deal was found by Cheapflights users on 1/12. 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 3/316:00 am
MDW
-
PUJ
1 stop7h 17m
Frontier
Tue 4/73:34 pm
PUJ
-
MDW
1 stop9h 08m
Frontier
Deal found 1/12$311

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Caribbean Islands 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 January 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Caribbean Islands that are best for you.

Fly from

Midway

Fly to

Caribbean Islands

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

1:35 pm-12:05 am

2 stops8h 30m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:10 am-1:55 pm

2 stops9h 45m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/27

8:30 am-5:05 pm

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-12:10 pm

1 stop8h 40m

$296

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

9:50 am-10:25 pm

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:10 am-1:55 pm

2 stops9h 45m

$296

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

9:50 am-10:25 pm

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:10 am-1:55 pm

2 stops9h 45m

$296

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/30

8:35 am-8:55 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:10 am-11:35 am

1 stop7h 25m

$315

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/31

12:15 pm-11:00 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Tue 2/3

5:40 am-2:15 pm

2 stops10h 35m

$315

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/29

3:15 pm-12:35 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Mon 2/2

2:35 pm-10:05 pm

2 stops9h 30m

$361

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/21

6:00 am-5:17 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:30 am-11:59 am

1 stop6h 29m

$376

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

6:00 am-2:31 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:09 am-11:59 am

1 stop7h 50m

$377

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/30

2:20 pm-12:35 am

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:35 pm-10:05 pm

2 stops9h 30m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Midway 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 Chicago Midway Airport to Caribbean Islands

What is the cheapest month to book a flight from Chicago Midway Airport to Caribbean Islands?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean Islands (average of $137). Flying from Chicago Midway Airport to Caribbean Islands in June is currently the most expensive (average of $298). 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 MDW to EPX?

Find hourly flight availability from Midway to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 12, 2026.

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

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated January 12, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Caribbean Islands, such as Southwest, Delta, and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,034 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,055 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Caribbean Islands. 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 Chicago Midway Airport to Caribbean Islands?

    Airlines like Southwest and Delta fly from Chicago Midway Airport to Caribbean Islands in about 8h 30m. The time it takes to get you to your destination can typically vary by up to 3h 15m. Airlines will cover a distance of 2057 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Chicago Midway Airport to Caribbean Islands?

    The most popular flight routes from Chicago Midway Airport to Caribbean Islands are Chicago Midway - San Juan Luis Munoz Marin Intl, Chicago Midway - Punta Cana and Chicago Midway - Oranjestad Reina Beatrix.

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

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

  • How can I find direct flights from Midway to Caribbean Islands?

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

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

    Yes. Cheapflights offers flight deals from Midway to Caribbean Islands 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 Chicago Midway Airport to Caribbean Islands?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean Islands (average of $137). Flying from Chicago Midway Airport to Caribbean Islands in June is currently the most expensive (average of $298). 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

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Alternative routes for Midway to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Midway to Caribbean Islands

Discover the top 3 airlines that operate flights from Midway to Caribbean Islands. 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 January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$376FlexibilityNo cancel feeOn-time62%
DeltaCheapest$325Average$593FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$381Average$668FlexibilityNo cancel feeOn-time63%

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