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$84+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$168
(Mytrip)

One-way from

$84
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$372

Good round-trip deal

$659 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. 15% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip 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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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.
Wed 3/54:20 pmMDW - SJU
1 stop26h 50mFrontier
Tue 3/116:00 amSJU - MDW
1 stop10h 32mFrontier
Deal found 2/19$168
This Delta deal was found by Cheapflights users on 2/20. 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 3/1112:51 pmMDW - SJU
1 stop9h 16mDelta
Tue 3/1812:54 pmSJU - MDW
1 stop10h 29mDelta
Deal found 2/20$271
This Booking.com deal was found by Cheapflights users on 2/19. 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 5/2512:46 pmMDW - PUJ
2 stops19h 05mFrontier
Wed 5/283:05 pmPUJ - MDW
1 stop9h 50mFrontier
Deal found 2/19$309
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/246:38 pmMDW - PUJ
2 stops19h 04mMultiple Airlines
Tue 4/11:14 pmPUJ - MDW
1 stop11h 10mMultiple Airlines
Deal found 2/19$319
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 3/611:00 amMDW - SJU
1 stop11h 30mSouthwest
Tue 3/115:35 amSJU - MDW
2 stops8h 45mSouthwest
Deal found 2/20$378
This Delta deal was found by Cheapflights users on 2/19. 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 3/36:00 amMDW - PUJ
1 stop6h 23mDelta
Tue 3/1112:50 pmPUJ - MDW
1 stop10h 33mDelta
Deal found 2/19$385
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Sun 4/62:16 pmMDW - SDQ
2 stops21h 17mFrontier
Sun 4/132:32 pmSDQ - MDW
2 stops22h 36mFrontier
Deal found 2/20$386
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 3/27:25 amMDW - SDQ
1 stop11h 35mMultiple Airlines
Mon 3/101:42 pmSDQ - MDW
2 stops26h 50mMultiple Airlines
Deal found 2/20$429
This Delta deal was found by Cheapflights users on 2/20. 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 5/46:04 amMDW - SDQ
1 stop6h 14mDelta
Sat 5/106:35 amSDQ - MDW
2 stops12h 55mDelta
Deal found 2/20$431
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/128:10 amMDW - MBJ
1 stop5h 50mSouthwest
Wed 3/191:35 pmMBJ - MDW
1 stop7h 15mSouthwest
Deal found 2/19$449
This Priceline deal was found by Cheapflights users on 2/19. 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.
Sun 5/44:00 pmMDW - MBJ
2 stops21h 01mFrontier
Sun 5/112:21 pmMBJ - MDW
1 stop9h 18mFrontier
Deal found 2/19$451
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/129:54 amMDW - MBJ
1 stop5h 29mDelta
Tue 3/181:25 pmMBJ - MDW
1 stop8h 58mDelta
Deal found 2/19$459

Find flights from Midway to Caribbean within your budget

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 February 20, 2025.

Fly from

Midway

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 3/5

4:20 pm-9:10 pm

1 stop26h 50m

San Juan Luis Munoz Marin Intl

Tue 3/11

6:00 am-3:32 pm

1 stop10h 32m

$168

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 3/11

12:51 pm-11:07 pm

1 stop9h 16m

San Juan Luis Munoz Marin Intl

Tue 3/18

12:54 pm-10:23 pm

1 stop10h 29m

$271

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 5/25

12:46 pm-8:51 am

2 stops19h 05m

Punta Cana

Wed 5/28

3:05 pm-11:55 pm

1 stop9h 50m

$309

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 3/24

6:38 pm-2:42 pm

2 stops19h 04m

Punta Cana

Tue 4/1

1:14 pm-11:24 pm

1 stop11h 10m

$319

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 3/6

11:00 am-12:30 am

1 stop11h 30m

San Juan Luis Munoz Marin Intl

Tue 3/11

5:35 am-1:20 pm

2 stops8h 45m

$378

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 3/3

6:00 am-2:23 pm

1 stop6h 23m

Punta Cana

Tue 3/11

12:50 pm-10:23 pm

1 stop10h 33m

$385

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 4/6

2:16 pm-12:33 pm

2 stops21h 17m

Santo Domingo Las Americas

Sun 4/13

2:32 pm-12:08 pm

2 stops22h 36m

$386

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 3/2

7:25 am-9:00 pm

1 stop11h 35m

Santo Domingo Las Americas

Mon 3/10

1:42 pm-3:32 pm

2 stops26h 50m

$429

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 5/4

6:04 am-1:18 pm

1 stop6h 14m

Santo Domingo Las Americas

Sat 5/10

6:35 am-6:30 pm

2 stops12h 55m

$431

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 3/12

8:10 am-2:00 pm

1 stop5h 50m

Montego Bay Sangster Intl

Wed 3/19

1:35 pm-8:50 pm

1 stop7h 15m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Midway to Caribbean

Get recent, data-driven insights about flights from Midway to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 20, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

KLM
7.8
Good
1,333 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,801 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $84. Delta flights start at $136 while deals on Southwest start at $161 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 - Punta Cana and Chicago Midway - Montego Bay Sangster Intl.

  • 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 March is currently the most expensive (average of $363). 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Midway to Caribbean

Discover the top 4 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$134Average$395FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$174Average$277FlexibilityNo cancel feeOn-time65%
DeltaCheapest$325Average$752FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$332Average$725FlexibilityNo cancel feeOn-time63%
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