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$117+ Cheap flights from Midway (MDW) 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from Midway to Caribbean

Keep the following information in mind while searching for Midway to Caribbean flight deals. Data was last updated July 29, 2025.

Round-trip from

$235
(Cheapflightsfares)

One-way from

$117
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$377

Good round-trip deal

$536 or less

Good one-way deal

$126 or less
From Chicago Midway to Caribbean
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One-way flight from Chicago Midway to Caribbean
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Highest demand for flights based on searches. 12% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago Midway to Caribbean.
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Price to beat on a one-way flight from Chicago Midway to Caribbean.
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Find flight deals from Midway to Caribbean

Cheapest flights from Midway to Caribbean
Explore the most affordable flight options available from Midway to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 9/136:15 amMDW - SJU
1 stop6h 56mFrontier
Fri 9/263:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 7/27$236
This Delta deal was found by Cheapflights users on 7/27. 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.
Mon 11/106:00 amMDW - PUJ
1 stop6h 23mDelta
Fri 11/143:50 pmPUJ - MDW
1 stop7h 54mDelta
Deal found 7/27$343
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/99:12 pmMDW - PUJ
2 stops43h 03mFrontier
Tue 8/123:25 pmPUJ - MDW
1 stop20h 15mFrontier
Deal found 7/28$352
This Southwest deal was found by Cheapflights users on 7/27. 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 10/35:00 amMDW - PUJ
1 stop8h 30mSouthwest
Wed 10/81:40 pmPUJ - MDW
1 stop9h 55mSouthwest
Deal found 7/27$368
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/107:23 pmMDW - AUA
1 stop17h 57mFrontier
Sat 10/253:35 pmAUA - MDW
1 stop8h 34mFrontier
Deal found 7/29$370
This Frontier deal was found by Cheapflights users on 7/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/511:39 amMDW - SDQ
1 stop11h 53mFrontier
Tue 8/121:48 amSDQ - MDW
1 stop9h 52mFrontier
Deal found 7/28$375
This FlightHub deal was found by Cheapflights users on 7/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:10 amMDW - MBJ
1 stop25h 43mFrontier
Sat 10/189:13 amMBJ - MDW
1 stop13h 56mFrontier
Deal found 7/27$381
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sun 9/215:45 amMDW - MBJ
1 stop6h 00mSouthwest
Wed 9/2412:55 pmMBJ - MDW
2 stops9h 30mSouthwest
Deal found 7/29$409
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/16:00 amMDW - MBJ
1 stop9h 36mDelta
Sat 9/61:20 pmMBJ - MDW
1 stop7h 52mDelta
Deal found 7/28$410
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:48 amMDW - MBJ
2 stops25h 17mMultiple Airlines
Mon 9/2910:52 amMBJ - MDW
1 stop7h 51mMultiple Airlines
Deal found 7/28$419
This Delta deal was found by Cheapflights users on 7/29. 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.
Sat 9/136:00 amMDW - SDQ
1 stop6h 40mDelta
Sat 9/203:06 pmSDQ - MDW
1 stop7h 04mDelta
Deal found 7/29$427
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/2010:51 amMDW - PUJ
1 stop23h 50mMultiple Airlines
Sat 9/2712:36 pmPUJ - MDW
1 stop21h 42mMultiple Airlines
Deal found 7/27$437

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 July 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Caribbean that are best for you.

Fly from

Midway

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/30

10:51 am-7:18 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-9:51 am

1 stop7h 12m

$235

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 11/10

6:00 am-2:23 pm

1 stop6h 23m

Punta Cana

Fri 11/14

3:50 pm-9:44 pm

1 stop7h 54m

$343

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/19

5:05 am-1:50 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 9/23

1:35 pm-10:25 pm

2 stops9h 50m

$351

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 8/9

9:12 pm-5:15 pm

2 stops43h 03m

Punta Cana

Tue 8/12

3:25 pm-10:40 am

1 stop20h 15m

$352

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 10/3

5:00 am-2:30 pm

1 stop8h 30m

Punta Cana

Wed 10/8

1:40 pm-10:35 pm

1 stop9h 55m

$368

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Fri 10/10

7:23 pm-2:20 pm

1 stop17h 57m

Oranjestad Reina Beatrix

Sat 10/25

3:35 pm-11:09 pm

1 stop8h 34m

$370

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 8/5

11:39 am-12:32 am

1 stop11h 53m

Santo Domingo Las Americas

Tue 8/12

1:48 am-10:40 am

1 stop9h 52m

$375

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/20

6:15 am-12:45 pm

1 stop6h 30m

Montego Bay Sangster Intl

Sun 9/21

2:12 pm-11:20 pm

1 stop9h 08m

$381

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/21

6:15 pm-3:34 pm

2 stops21h 19m

Montego Bay Sangster Intl

Fri 9/26

4:59 pm-12:28 pm

2 stops19h 29m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/21

5:45 am-11:45 am

1 stop6h 00m

Montego Bay Sangster Intl

Wed 9/24

12:55 pm-10:25 pm

2 stops9h 30m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $254). Flying from Chicago Midway Airport to Caribbean 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 CB?

Find hourly flight availability from Midway 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 July 29, 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 as you normally would.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated July 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, and LATAM Airlines from Chicago Midway Airport to Caribbean. 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
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

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
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

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
1,822 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

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
2,972 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

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
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

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. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Caribbean one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $117. Delta flights start at $160 while deals on Southwest start at $176 one-way.

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

    The most popular flight routes from Chicago Midway Airport to Caribbean are Chicago Midway - San Juan Luis Munoz Marin Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago Midway - Punta Cana.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $254). Flying from Chicago Midway Airport to Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Mexico City flights
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O'Hare Intl to Raleigh flights
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Top 5 airlines flying from Midway to Caribbean

Discover the top 5 airlines that operate flights from Midway 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 July 29, 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$667FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$352Average$682FlexibilityNo cancel feeOn-time63%

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