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$94+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Dec 26 — Jan 21
Thu 12/26
Thu 1/2
1 adult, Economy
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Cheap flight deals from Midway to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Caribbean (0CB). 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 21, 2024.

Round-trip from

$163
(Frontier)

One-way from

$94
(Trip.com)
From Chicago Midway to Caribbean
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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 December 21, 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 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 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 Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/247:45 amMDW - SDQ
1 stop26h 38mFrontier
Thu 12/268:55 pmSDQ - MDW
1 stop13h 26mFrontier
Deal found 12/20$553
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/227:40 pmMDW - SJU
1 stop12h 45mSouthwest
Wed 12/256:10 amSJU - MDW
1 stop10h 05mSouthwest
Deal found 12/20$554
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 Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/318:35 pmMDW - PLS
2 stops17h 25mSouthwest
Wed 1/83:55 pmPLS - MDW
1 stop6h 50mSouthwest
Deal found 12/19$683
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.
Thu 12/2612:58 pmMDW - MBJ
2 stops23h 32mMultiple Airlines
Tue 12/3110:29 amMBJ - MDW
1 stop27h 55mMultiple Airlines
Deal found 12/19$685
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Tue 12/317:35 amMDW - NAS
1 stop12h 05mMultiple Airlines
Wed 1/112:00 pmNAS - MDW
2 stops19h 39mMultiple Airlines
Deal found 12/21$703
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/308:25 amMDW - MBJ
1 stop23h 44mFrontier
Sun 1/51:29 pmMBJ - MDW
2 stops24h 37mFrontier
Deal found 12/20$719
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:00 amMDW - PUJ
1 stop6h 45mSouthwest
Sat 12/284:55 pmPUJ - MDW
Nonstop5h 00mSouthwest
Deal found 12/20$723
This Delta deal was found by Cheapflights users on 12/21. 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.
Mon 12/236:00 amMDW - STT
1 stop6h 56mDelta
Fri 12/272:01 pmSTT - MDW
1 stop10h 05mDelta
Deal found 12/21$788

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 December 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/13

7:25 pm-10:44 am

1 stop13h 19m

San Juan Luis Munoz Marin Intl

Fri 2/14

4:28 pm-11:58 pm

1 stop9h 30m

$163

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

Wed 1/15

1:20 pm-12:40 am

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Thu 1/23

2:55 pm-7:45 pm

1 stop6h 50m

$279

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

3:48 pm-10:20 pm

1 stop8h 32m

$363

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 4/2

12:40 pm-1:44 pm

1 stop24h 04m

Santo Domingo Las Americas

Sun 4/6

2:54 pm-12:08 pm

2 stops22h 14m

$443

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 1/22

8:01 pm-10:34 am

1 stop13h 33m

Montego Bay Sangster Intl

Sun 1/26

11:48 am-9:32 pm

1 stop10h 44m

$446

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Fri 1/24

6:00 am-1:57 pm

1 stop5h 57m

Santo Domingo Las Americas

Fri 1/31

3:22 pm-10:20 pm

1 stop8h 58m

$450

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 1/30

7:21 pm-12:10 pm

2 stops15h 49m

Montego Bay Sangster Intl

Sun 2/2

11:48 am-9:32 pm

1 stop10h 44m

$457

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

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

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 $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 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 December 21, 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 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 December 21, 2024.
Southwest
8.1
Very good
4,814 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.7

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
4,814 reviews
Southwest
8.1
Very good
4,814 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.7

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
8,597 reviews
Southwest
8.1
Very good
4,814 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.7

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
1,873 reviews
Southwest
8.1
Very good
4,814 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.7

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
2,814 reviews
Southwest
8.1
Very good
4,814 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.7

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
3,474 reviews
Southwest
8.1
Very good
4,814 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.7

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. 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 $94. Southwest flights start at $117 while deals on Delta start at $162 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 $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

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to LaGuardia 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 December 21, 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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