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Caribbean Islands

$92+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Dec 25 — Jan 11
Wed 12/25
Wed 1/1
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 December 20, 2024.

Round-trip from

$161
(FlightHub)

One-way from

$92
(Trip.com)
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 December 20, 2024.

This FlightHub deal was found by Cheapflights users on 12/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/309:59 pmMDW - SJU
1 stop23h 55mFrontier
Sat 1/189:15 pmSJU - MDW
1 stop14h 47mFrontier
Deal found 12/20$294
This Mytrip deal was found by Cheapflights users on 12/19. 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.
Mon 12/239:16 amMDW - SDQ
1 stop23h 09mFrontier
Thu 12/268:55 pmSDQ - MDW
1 stop13h 26mFrontier
Deal found 12/19$447
This FlightHub deal was found by Cheapflights users on 12/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/272:35 pmMDW - PUJ
1 stop20h 14mFrontier
Mon 12/301:59 pmPUJ - MDW
1 stop11h 15mFrontier
Deal found 12/19$449
This Kiwi.com deal was found by Cheapflights users on 12/19. 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.
Tue 12/316:49 pmMDW - MBJ
1 stop17h 56mMultiple Airlines
Thu 1/911:44 amMBJ - MDW
1 stop7h 53mMultiple Airlines
Deal found 12/19$515
This eDestinos deal was found by Cheapflights users on 12/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/262:31 pmMDW - SJU
2 stops32h 54mMultiple Airlines
Fri 1/107:12 pmSJU - MDW
2 stops30h 17mMultiple Airlines
Deal found 12/20$523
This Southwest deal was found by Cheapflights users on 12/18. 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 12/2411:55 amMDW - SJU
2 stops10h 50mSouthwest
Wed 12/257:55 amSJU - MDW
2 stops13h 00mSouthwest
Deal found 12/18$533
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/302:20 pmMDW - MBJ
1 stop17h 49mFrontier
Thu 1/911:44 amMBJ - MDW
1 stop7h 53mFrontier
Deal found 12/19$570
This Southwest deal was found by Cheapflights users on 12/18. 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 12/318:00 amMDW - PLS
1 stop6h 00mSouthwest
Wed 1/83:55 pmPLS - MDW
1 stop6h 50mSouthwest
Deal found 12/18$639
This Kiwi.com deal was found by Cheapflights users on 12/19. 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.
Fri 12/276:00 amMDW - SDQ
2 stops39h 37mMultiple Airlines
Tue 12/319:00 amSDQ - MDW
1 stop8h 13mMultiple Airlines
Deal found 12/19$644
This Delta deal was found by Cheapflights users on 12/18. 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 12/196:00 amMDW - PUJ
1 stop8h 34mDelta
Thu 12/263:50 pmPUJ - MDW
1 stop8h 16mDelta
Deal found 12/18$679
This Delta deal was found by Cheapflights users on 12/19. 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.
Tue 12/316:00 amMDW - MBJ
1 stop7h 48mDelta
Wed 1/224:49 pmMBJ - MDW
1 stop6h 31mDelta
Deal found 12/19$719
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
Tue 12/244:08 pmMDW - NAS
1 stop19h 27mMultiple Airlines
Tue 12/315:30 pmNAS - MDW
1 stop15h 51mMultiple Airlines
Deal found 12/18$724

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 December 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/26

7:25 am-1:59 am

1 stop16h 34m

San Juan Luis Munoz Marin Intl

Thu 1/30

6:55 pm-2:42 pm

1 stop21h 47m

$161

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 2/27

4:13 pm-2:00 pm

1 stop19h 47m

Punta Cana

Mon 3/3

3:10 pm-7:32 am

1 stop18h 22m

$258

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/28

10:05 am-12:25 am

2 stops12h 20m

San Juan Luis Munoz Marin Intl

Sat 2/1

2:55 pm-6:10 pm

Nonstop5h 15m

$300

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/25

3:41 pm-11:46 pm

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Sat 2/1

7:30 am-2:53 pm

1 stop9h 23m

$324

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 1/14

6:00 am-2:23 pm

1 stop6h 23m

Punta Cana

Thu 1/23

4:50 pm-10:20 pm

1 stop7h 30m

$363

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 3/1

10:43 am-1:08 pm

2 stops24h 25m

Santo Domingo Las Americas

Sun 3/16

2:59 pm-7:35 pm

1 stop29h 36m

$419

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 1/15

9:34 am-12:56 am

2 stops13h 22m

Santo Domingo Las Americas

Sat 1/18

3:22 pm-10:20 pm

1 stop8h 58m

$455

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/25

6:35 am-3:25 pm

1 stop6h 50m

Punta Cana

Sat 2/1

5:00 pm-8:00 pm

Nonstop5h 00m

$458

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/9

7:32 pm-12:59 am

2 stops27h 27m

San Juan Luis Munoz Marin Intl

Mon 1/20

10:09 pm-4:16 pm

2 stops20h 07m

$461

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 2/11

5:31 pm-3:43 pm

2 stops20h 12m

Punta Cana

Fri 2/14

1:39 pm-7:19 pm

1 stop7h 40m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

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 $380). 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 December 20, 2024.

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 December 20, 2024.
Peruse reviews from past customers who have flown with Frontier, Southwest and Delta 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
4,821 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

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
4,821 reviews
Southwest
8.1
Very good
4,821 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

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
8,601 reviews
Southwest
8.1
Very good
4,821 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

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
1,876 reviews
Southwest
8.1
Very good
4,821 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

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
7.3
Good
2,816 reviews
Southwest
8.1
Very good
4,821 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

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.

Frontier
6.1
Okay
3,475 reviews
Southwest
8.1
Very good
4,821 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

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 $92. 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 $380). 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 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 December 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$391FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$199Average$284FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$304Average$680FlexibilityNo cancel feeOn-time63%
DeltaCheapest$374Average$754FlexibilityNo cancel feeOn-timeN/A
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