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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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
May 20 — May 271
Tue 5/20
Tue 5/27
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 15, 2025.

Round-trip from

$277
(Frontier)

One-way from

$116
(Southwest)

Popular in

December

Cheapest in

August

Average price

$343

Good round-trip deal

$586 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. 14% potential increase in price ($61 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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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 15, 2025.

This Frontier deal was found by Cheapflights users on 5/15. 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 8/1211:39 amMDW - SJU
2 stops12h 20mFrontier
Fri 8/152:05 pmSJU - MDW
2 stops10h 12mFrontier
Deal found 5/15$262
This Delta deal was found by Cheapflights users on 5/14. 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.
Fri 8/86:00 amMDW - PUJ
1 stop7h 51mDelta
Fri 8/151:10 pmPUJ - MDW
1 stop9h 37mDelta
Deal found 5/14$335
This Mytrip deal was found by Cheapflights users on 5/15. 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.
Fri 6/132:53 pmMDW - SJU
3 stops42h 46mMultiple Airlines
Sun 6/158:24 pmSJU - MDW
2 stops24h 22mMultiple Airlines
Deal found 5/15$342
This Frontier deal was found by Cheapflights users on 5/14. 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 18mFrontier
Sat 8/303:35 pmAUA - MDW
1 stop8h 34mFrontier
Deal found 5/14$381
This Southwest deal was found by Cheapflights users on 5/14. 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 10/165:35 amMDW - SJU
1 stop8h 10mSouthwest
Tue 10/215:05 amSJU - MDW
1 stop9h 55mSouthwest
Deal found 5/14$391
This Delta deal was found by Cheapflights users on 5/14. 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 9/66:00 amMDW - SDQ
1 stop6h 24mDelta
Sat 9/133:12 pmSDQ - MDW
1 stop7h 32mDelta
Deal found 5/14$407
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 7/59:12 pmMDW - PUJ
1 stop10h 42mMultiple Airlines
Sat 7/1212:40 pmPUJ - MDW
1 stop8h 42mMultiple Airlines
Deal found 5/13$415
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
Thu 7/109:12 pmMDW - SDQ
1 stop26h 56mMultiple Airlines
Thu 7/1711:50 amSDQ - MDW
1 stop28h 16mMultiple Airlines
Deal found 5/15$415
This Gotogate deal was found by Cheapflights users on 5/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/46:40 amMDW - PUJ
1 stop7h 23mFrontier
Tue 6/103:27 pmPUJ - MDW
1 stop22h 28mFrontier
Deal found 5/14$417
This Mytrip deal was found by Cheapflights users on 5/15. 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.
Fri 5/308:04 pmMDW - STT
3 stops36h 53mMultiple Airlines
Thu 6/510:52 amSTT - MDW
2 stops33h 54mMultiple Airlines
Deal found 5/15$426
This Delta deal was found by Cheapflights users on 5/15. 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 7/166:00 amMDW - PLS
1 stop5h 35mDelta
Sun 7/202:00 pmPLS - MDW
1 stop8h 41mDelta
Deal found 5/15$435
This Frontier deal was found by Cheapflights users on 5/14. 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 6/122:55 pmMDW - SDQ
1 stop8h 24mFrontier
Sun 6/1511:49 amSDQ - MDW
1 stop9h 28mFrontier
Deal found 5/14$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 May 15, 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

Tue 8/12

11:39 am-12:59 am

2 stops12h 20m

San Juan Luis Munoz Marin Intl

Fri 8/15

2:05 pm-11:17 pm

2 stops10h 12m

$262

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 8/8

6:00 am-2:51 pm

1 stop7h 51m

Punta Cana

Fri 8/15

1:10 pm-9:47 pm

1 stop9h 37m

$335

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 6/13

2:53 pm-10:39 am

3 stops42h 46m

San Juan Luis Munoz Marin Intl

Sun 6/15

8:24 pm-7:46 pm

2 stops24h 22m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/5

9:12 pm-8:54 am

1 stop10h 42m

Punta Cana

Sat 7/12

12:40 pm-8:22 pm

1 stop8h 42m

$415

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 7/10

9:12 pm-1:08 am

1 stop26h 56m

Santo Domingo Las Americas

Thu 7/17

11:50 am-3:06 pm

1 stop28h 16m

$415

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 6/4

6:40 am-3:03 pm

1 stop7h 23m

Punta Cana

Tue 6/10

3:27 pm-12:55 pm

1 stop22h 28m

$417

ChicagoOranjestad

MDW - AUA

MDWAUA

Chicago Midway

Sat 6/21

6:20 am-2:29 pm

1 stop7h 09m

Oranjestad Reina Beatrix

Sat 7/5

3:35 pm-10:35 pm

1 stop8h 00m

$425

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 5/30

8:04 pm-9:57 am

3 stops36h 53m

Saint Thomas Island Cyril E King

Thu 6/5

10:52 am-7:46 pm

2 stops33h 54m

$426

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 6/9

8:00 am-6:50 pm

2 stops9h 50m

San Juan Luis Munoz Marin Intl

Wed 6/18

11:35 am-8:35 pm

2 stops10h 00m

$431

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Wed 7/16

6:00 am-12:35 pm

1 stop5h 35m

Providenciales

Sun 7/20

2:00 pm-9:41 pm

1 stop8h 41m

$435

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/14

Showing 1-10 of 60 results
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2
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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 15, 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 15, 2025.
Southwest
8.0
Very good
4,291 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

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
4,291 reviews
Southwest
8.0
Very good
4,291 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

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
7,946 reviews
Southwest
8.0
Very good
4,291 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

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
2,841 reviews
Southwest
8.0
Very good
4,291 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

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
3,284 reviews
Southwest
8.0
Very good
4,291 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

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 $143 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 $618, our data shows the cheapest flight currently is $574. When looking at the most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), you can expect to pay $226 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 Dallas/Fort Worth flights
O'Hare Intl to Vancouver Intl flights
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O'Hare Intl to Baltimore flights
O'Hare Intl to Austin flights
O'Hare Intl to George Bush Intcntl flights

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 May 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$133Average$401FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$283FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$720FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$347Average$707FlexibilityNo cancel feeOn-time63%

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