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Caribbean Islands

$82+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
janv. 26 — févr. 21
dim. 1/26
dim. 2/2
1 adult, Economy
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Cheap flight deals from Midway to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated janvier 21, 2025.

Round-trip from

$160
(FlightHub)

One-way from

$83
(Cheapflightsfares)
From Chicago Midway to Caribbean Islands
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One-way flight from Chicago Midway to Caribbean Islands
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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 janvier 21, 2025.

This FlightHub deal was found by Cheapflights users on 1/21. 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.
mar. 4/12:36 pmMDW - SJU
1 stop8h 18mFrontier
lun. 4/75:01 amSJU - MDW
1 stop15h 45mFrontier
Deal found 1/21$160
This Southwest deal was found by Cheapflights users on 1/20. 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.
dim. 2/21:20 pmMDW - SJU
2 stops9h 30mSouthwest
ven. 2/71:45 pmSJU - MDW
1 stop10h 15mSouthwest
Deal found 1/20$235
This CheapOair deal was found by Cheapflights users on 1/21. 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.
mar. 4/12:36 pmMDW - PUJ
1 stop18h 42mFrontier
lun. 4/72:49 pmPUJ - MDW
1 stop10h 01mFrontier
Deal found 1/21$309
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 1/286:00 amMDW - SJU
1 stop9h 14mDelta
ven. 2/77:30 amSJU - MDW
1 stop10h 50mDelta
Deal found 1/21$325
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 2/186:00 amMDW - PUJ
1 stop7h 25mDelta
jeu. 2/272:00 pmPUJ - MDW
1 stop10h 20mDelta
Deal found 1/21$355
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
lun. 3/106:38 pmMDW - PUJ
2 stops16h 06mMultiple Airlines
lun. 3/172:15 pmPUJ - MDW
1 stop10h 43mMultiple Airlines
Deal found 1/21$378
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
mar. 2/45:31 pmMDW - SDQ
2 stops20h 23mMultiple Airlines
sam. 2/159:00 amSDQ - MDW
1 stop11h 15mMultiple Airlines
Deal found 1/20$393
This eDestinos deal was found by Cheapflights users on 1/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 3/84:40 pmMDW - SDQ
2 stops19h 09mFrontier
lun. 3/1712:04 pmSDQ - MDW
2 stops28h 49mFrontier
Deal found 1/21$402
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
jeu. 5/86:30 pmMDW - MBJ
1 stop18h 31mFrontier
lun. 5/122:21 pmMBJ - MDW
1 stop9h 18mFrontier
Deal found 1/21$403
This Delta deal was found by Cheapflights users on 1/21. 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.
sam. 2/89:33 amMDW - SDQ
2 stops13h 23mDelta
mer. 2/127:05 amSDQ - MDW
2 stops13h 06mDelta
Deal found 1/21$421
This Southwest deal was found by Cheapflights users on 1/21. 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.
dim. 4/69:05 amMDW - MBJ
Nonstop4h 00mSouthwest
mer. 4/912:00 pmMBJ - MDW
1 stop7h 50mSouthwest
Deal found 1/21$476
This Delta deal was found by Cheapflights users on 1/21. 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.
mer. 3/1912:51 pmMDW - MBJ
1 stop7h 53mDelta
mar. 3/257:00 amMBJ - MDW
1 stop9h 14mDelta
Deal found 1/21$481

Find flights from Midway to Caribbean Islands within your budget

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 janvier 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 4/1

2:36 pm-11:54 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

lun. 4/7

5:01 am-7:46 pm

1 stop15h 45m

$160

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

dim. 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

ven. 2/7

1:45 pm-10:00 pm

1 stop10h 15m

$235

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 4/1

2:36 pm-10:18 am

1 stop18h 42m

Punta Cana

lun. 4/7

2:49 pm-11:50 pm

1 stop10h 01m

$309

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 5/6

10:10 am-7:39 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

jeu. 5/8

6:15 am-2:54 pm

1 stop9h 39m

$325

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 2/18

6:00 am-3:25 pm

1 stop7h 25m

Punta Cana

ven. 2/28

2:00 pm-10:20 pm

1 stop10h 20m

$355

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 3/10

6:38 pm-11:44 am

2 stops16h 06m

Punta Cana

lun. 3/17

2:15 pm-11:58 pm

1 stop10h 43m

$378

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

mar. 2/4

5:31 pm-3:54 pm

2 stops20h 23m

Santo Domingo Las Americas

sam. 2/15

9:00 am-6:15 pm

1 stop11h 15m

$393

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

sam. 3/8

4:40 pm-1:49 pm

2 stops19h 09m

Santo Domingo Las Americas

lun. 3/17

12:04 pm-3:53 pm

2 stops28h 49m

$402

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

jeu. 5/8

6:30 pm-1:01 pm

1 stop18h 31m

Montego Bay Sangster Intl

lun. 5/12

2:21 pm-11:39 pm

1 stop9h 18m

$403

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

sam. 2/8

10:57 am-12:56 am

2 stops11h 59m

Santo Domingo Las Americas

mer. 2/12

3:22 pm-10:20 pm

1 stop8h 58m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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.

Travel insights for flights from Midway to Caribbean Islands

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

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 March is currently the most expensive (average of $378). 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 janvier 21, 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.

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 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 janvier 21, 2025.
Peruse reviews from past customers who have flown with Frontier, Delta and Southwest from Chicago to Caribbean Islands to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

KLM
7.8
Good
1,341 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

LATAM Airlines
7.5
Good
1,858 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.2
Good
2,829 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 cheapest airlines to fly from Chicago Midway Airport to Caribbean Islands one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $83. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago Midway Airport to Caribbean Islands for a low price.

  • 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 March is currently the most expensive (average of $378). 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.

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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 4 airlines flying from Midway to Caribbean Islands

Discover the top 4 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 janvier 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$135Average$399FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$199Average$283FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$317Average$721FlexibilityNo cancel feeOn-time63%
DeltaCheapest$354Average$768FlexibilityNo cancel feeOn-timeN/A
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