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$116+ 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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$298
(Frontier)

One-way from

$116
(Southwest)

Popular in

December

Cheapest in

August

Average price

$334

Good round-trip deal

$397 or less

Good one-way deal

$308 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 ($67 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 May 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 May 1, 2025.

This Frontier deal was found by Cheapflights users on 4/30. 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.
Thu 5/81:19 pmMDW - SJU
1 stop9h 46mFrontier
Wed 5/143:56 amSJU - MDW
1 stop9h 28mFrontier
Deal found 4/30$298
This Delta deal was found by Cheapflights users on 4/30. 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 8/116:00 amMDW - PUJ
1 stop6h 17mDelta
Fri 8/151:10 pmPUJ - MDW
1 stop9h 37mDelta
Deal found 4/30$335
This Trip.com deal was found by Cheapflights users on 4/30. 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 5/212:15 pmMDW - SJU
1 stop12h 35mMultiple Airlines
Wed 6/42:54 pmSJU - MDW
1 stop8h 44mMultiple Airlines
Deal found 4/30$337
This Delta deal was found by Cheapflights users on 4/30. 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 5/1412:48 pmMDW - SJU
1 stop8h 59mDelta
Sat 5/176:15 amSJU - MDW
1 stop6h 38mDelta
Deal found 4/30$385
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/99:12 pmMDW - PUJ
2 stops14h 43mMultiple Airlines
Thu 6/1210:06 amPUJ - MDW
1 stop11h 11mMultiple Airlines
Deal found 4/30$394
This Southwest deal was found by Cheapflights users on 4/29. 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.
Tue 9/167:30 amMDW - SJU
1 stop6h 25mSouthwest
Tue 9/237:20 amSJU - MDW
1 stop10h 05mSouthwest
Deal found 4/29$397
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sat 7/58:55 amMDW - PUJ
Nonstop4h 30mSouthwest
Sat 7/123:40 pmPUJ - MDW
1 stop8h 50mSouthwest
Deal found 4/30$410
This Frontier deal was found by Cheapflights users on 4/30. 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.
Fri 5/239:12 pmMDW - PUJ
1 stop12h 38mFrontier
Sun 6/110:17 amPUJ - MDW
1 stop13h 15mFrontier
Deal found 4/30$421
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/2910:25 amMDW - SDQ
2 stops13h 09mDelta
Thu 6/57:00 amSDQ - MDW
2 stops12h 45mDelta
Deal found 4/30$421
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 7/266:20 amMDW - AUA
1 stop7h 19mFrontier
Sat 8/23:45 pmAUA - MDW
1 stop7h 50mFrontier
Deal found 5/1$435
This CheapOair deal was found by Cheapflights users on 4/30. 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.
Tue 5/274:46 pmMDW - MBJ
1 stop15h 04mFrontier
Sat 5/318:55 amMBJ - MDW
1 stop13h 22mFrontier
Deal found 4/30$447
This Booking.com deal was found by Cheapflights users on 4/30. 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.
Mon 7/286:40 pmMDW - SDQ
1 stop16h 09mFrontier
Sun 8/311:50 amSDQ - MDW
2 stops47h 50mFrontier
Deal found 4/30$448

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 May 1, 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

Thu 5/8

1:19 pm-12:05 am

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Wed 5/14

3:56 am-12:24 pm

1 stop9h 28m

$298

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 8/11

6:00 am-1:17 pm

1 stop6h 17m

Punta Cana

Fri 8/15

1:10 pm-9:47 pm

1 stop9h 37m

$335

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/5

12:15 pm-1:50 am

1 stop12h 35m

San Juan Luis Munoz Marin Intl

Wed 6/4

2:54 pm-10:38 pm

1 stop8h 44m

$337

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 5/14

12:48 pm-10:47 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Sat 5/17

6:15 am-11:53 am

1 stop6h 38m

$385

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 6/9

9:12 pm-12:55 pm

2 stops14h 43m

Punta Cana

Thu 6/12

10:06 am-8:17 pm

1 stop11h 11m

$394

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 7/5

8:50 am-2:35 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Wed 7/9

4:15 pm-11:00 pm

1 stop7h 45m

$407

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/5

8:55 am-2:25 pm

Nonstop4h 30m

Punta Cana

Sat 7/12

3:40 pm-11:30 pm

1 stop8h 50m

$410

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 5/23

9:12 pm-10:50 am

1 stop12h 38m

Punta Cana

Sun 6/1

10:17 am-10:32 pm

1 stop13h 15m

$421

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 5/29

10:25 am-12:34 am

2 stops13h 09m

Santo Domingo Las Americas

Thu 6/5

7:00 am-6:45 pm

2 stops12h 45m

$421

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sat 7/26

6:20 am-2:39 pm

1 stop7h 19m

Oranjestad Reina Beatrix

Sat 8/2

3:45 pm-10:35 pm

1 stop7h 50m

$435

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 December is currently the most expensive (average of $336). 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 May 1, 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 May 1, 2025.
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
LATAM Airlines
7.5
Good
1,767 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Southwest, which is currently one of the cheapest options available, starting at $116. Frontier flights start at $146 while deals on Delta start at $156 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.

  • What are the cheapest flights from Chicago Midway Airport to Caribbean?

    While on average a flight from Chicago Midway Airport to Caribbean is generally $362, our data shows the cheapest flight currently is $243. When looking at the most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), you can expect to pay $261 for that flight.

  • 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 December is currently the most expensive (average of $336). 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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Midway to Atlanta flights
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O'Hare Intl to Austin flights
O'Hare Intl to Istanbul flights
Midway to Hobby flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Madrid flights
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O'Hare Intl to Charlotte flights

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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$133Average$402FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$293FlexibilityNo cancel feeOn-time65%
DeltaCheapest$325Average$745FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$712FlexibilityNo cancel feeOn-time63%

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