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Caribbean Islands

$115+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
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 August 7, 2025.

Round-trip from

$235
(Cheapflightsfares)

One-way from

$115
(SmartFares)

Popular in

December

Cheapest in

September

Average price

$326
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. 12% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 7, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:15 amMDW - SJU
1 stop6h 56mFrontier
Fri 9/263:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 8/5$235
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:15 amMDW - SJU
1 stop6h 56mFrontier
Fri 9/123:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 8/5$236
This Priceline deal was found by Cheapflights users on 8/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3010:51 amMDW - SJU
1 stop21h 08mFrontier
Sat 9/63:16 pmSJU - MDW
1 stop9h 01mFrontier
Deal found 8/5$239
This Cheapflightsfares deal was found by Cheapflights users on 8/6. 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 9/156:20 amMDW - SJU
1 stop6h 51mFrontier
Fri 9/263:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 8/6$247
This SmartFares deal was found by Cheapflights users on 8/6. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:15 amMDW - SJU
1 stop7h 00mFrontier
Fri 10/243:40 amSJU - MDW
1 stop7h 46mFrontier
Deal found 8/6$254
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/146:20 amMDW - SJU
1 stop6h 51mFrontier
Fri 9/193:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 8/5$255
This Frontier deal was found by Cheapflights users on 8/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2310:51 amMDW - SJU
1 stop7h 27mFrontier
Sun 8/243:59 amSJU - MDW
1 stop12h 30mFrontier
Deal found 8/6$258
This Priceline deal was found by Cheapflights users on 8/6. 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.
Sat 8/3010:51 amMDW - SJU
1 stop14h 59mFrontier
Thu 9/412:28 amSJU - MDW
1 stop7h 43mFrontier
Deal found 8/6$259
This Southwest deal was found by Cheapflights users on 8/5. 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.
Mon 9/15:10 amMDW - PUJ
1 stop7h 55mSouthwest
Fri 9/53:05 pmPUJ - MDW
1 stop7h 30mSouthwest
Deal found 8/5$343
This Delta deal was found by Cheapflights users on 8/6. 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.
Tue 10/146:23 pmMDW - PUJ
2 stops17h 05mDelta
Thu 10/232:49 pmPUJ - MDW
1 stop8h 25mDelta
Deal found 8/6$347
This Frontier deal was found by Cheapflights users on 8/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:10 amMDW - AUA
1 stop7h 19mFrontier
Sat 8/303:35 pmAUA - MDW
1 stop8h 33mFrontier
Deal found 8/6$355
This Frontier deal was found by Cheapflights users on 8/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:10 amMDW - PUJ
1 stop6h 57mFrontier
Sat 10/253:22 pmPUJ - MDW
1 stop8h 47mFrontier
Deal found 8/6$363

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 August 7, 2025.
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

Sat 9/20

6:15 am-2:11 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

$235

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/6

6:15 am-2:11 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Fri 9/12

3:39 am-9:51 am

1 stop7h 12m

$236

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/30

10:51 am-8:59 am

1 stop21h 08m

San Juan Luis Munoz Marin Intl

Sat 9/6

3:16 pm-11:17 pm

1 stop9h 01m

$239

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 9/15

6:20 am-2:11 pm

1 stop6h 51m

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

$247

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 10/17

6:15 am-2:15 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Fri 10/24

3:40 am-10:26 am

1 stop7h 46m

$254

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 9/14

6:20 am-2:11 pm

1 stop6h 51m

San Juan Luis Munoz Marin Intl

Fri 9/19

3:39 am-9:51 am

1 stop7h 12m

$255

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/23

10:51 am-7:18 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Sun 8/24

3:59 am-3:29 pm

1 stop12h 30m

$258

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/30

10:51 am-2:50 am

1 stop14h 59m

San Juan Luis Munoz Marin Intl

Thu 9/4

12:28 am-7:11 am

1 stop7h 43m

$259

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 9/1

5:10 am-2:05 pm

1 stop7h 55m

Punta Cana

Fri 9/5

3:05 pm-9:35 pm

1 stop7h 30m

$343

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 10/14

6:23 pm-12:28 pm

2 stops17h 05m

Punta Cana

Thu 10/23

2:49 pm-10:14 pm

1 stop8h 25m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean Islands (average of $254). Flying from Chicago Midway Airport to Caribbean Islands in June is currently the most expensive (average of $339). 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 August 7, 2025.

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 August 7, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Caribbean Islands, such as Southwest, Delta, and LATAM Airlines. 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
4,247 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,987 reviews
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
LATAM Airlines
7.5
Good
1,834 reviews
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
WestJet
7.2
Good
3,002 reviews
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,230 reviews
Southwest
8.0
Very good
4,247 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 - Montego Bay Sangster Intl.

  • 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean Islands (average of $254). Flying from Chicago Midway Airport to Caribbean Islands in June is currently the most expensive (average of $339). 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 5 airlines flying from Midway to Caribbean Islands

Discover the top 5 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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$133Average$335FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$365FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$657FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$352Average$682FlexibilityNo cancel feeOn-time63%

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