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$88+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

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 November 20, 2024.

This Trip.com deal was found by Cheapflights users on 11/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
Thu 12/193:59 amSJU - MDW
1 stop7h 32mFrontier
Deal found 11/20$174
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1512:36 pmMDW - SJU
2 stops35h 21mMultiple Airlines
Wed 1/224:53 pmSJU - MDW
2 stops27h 33mMultiple Airlines
Deal found 11/19$240
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/136:48 pmMDW - PUJ
1 stop14h 43mFrontier
Mon 12/1612:46 pmPUJ - MDW
1 stop26h 23mFrontier
Deal found 11/19$270
This Southwest deal was found by Cheapflights users on 11/19. 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.
Thu 12/121:30 pmMDW - SJU
1 stop9h 15mSouthwest
Sat 12/147:20 amSJU - MDW
2 stops8h 50mSouthwest
Deal found 11/19$297
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/106:00 amMDW - SJU
1 stop9h 15mDelta
Mon 12/163:25 pmSJU - MDW
1 stop8h 41mDelta
Deal found 11/20$379
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/154:27 pmMDW - PUJ
3 stops43h 33mMultiple Airlines
Sun 1/126:51 pmPUJ - MDW
2 stops22h 42mMultiple Airlines
Deal found 11/19$419
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/86:00 amMDW - PUJ
1 stop6h 25mDelta
Wed 12/113:50 pmPUJ - MDW
1 stop8h 16mDelta
Deal found 11/20$438
This Delta deal was found by Cheapflights users on 11/19. 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.
Mon 12/96:00 amMDW - MBJ
1 stop7h 04mDelta
Fri 12/133:29 pmMBJ - MDW
1 stop7h 37mDelta
Deal found 11/19$468
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/317:35 amMDW - NAS
1 stop12h 05mMultiple Airlines
Thu 1/97:45 amNAS - MDW
1 stop8h 23mMultiple Airlines
Deal found 11/19$483
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/246:49 pmMDW - MBJ
1 stop17h 56mMultiple Airlines
Tue 12/312:38 pmMBJ - MDW
2 stops23h 46mMultiple Airlines
Deal found 11/19$494
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Thu 12/1212:36 pmMDW - SDQ
2 stops31h 14mMultiple Airlines
Tue 12/1712:02 pmSDQ - MDW
1 stop7h 52mMultiple Airlines
Deal found 11/20$496
This FlightHub deal was found by Cheapflights users on 11/19. 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.
Sat 12/77:15 amMDW - MBJ
1 stop24h 39mFrontier
Tue 12/102:17 pmMBJ - MDW
1 stop22h 25mFrontier
Deal found 11/19$511

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/16

7:25 am-1:57 am

1 stop16h 32m

San Juan Luis Munoz Marin Intl

Fri 12/20

6:00 am-1:06 pm

1 stop9h 06m

$174

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

Wed 2/5

2:55 pm-7:45 pm

1 stop6h 50m

$210

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/9

3:04 pm-6:02 pm

1 stop24h 58m

San Juan Luis Munoz Marin Intl

Sat 1/25

8:00 am-11:29 pm

2 stops17h 29m

$239

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 12/13

6:48 pm-11:31 am

1 stop14h 43m

Punta Cana

Mon 12/16

12:46 pm-1:09 pm

1 stop26h 23m

$270

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/28

6:00 am-2:20 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Fri 2/7

2:02 pm-10:20 pm

1 stop10h 18m

$334

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 1/13

6:00 am-3:25 pm

1 stop7h 25m

Punta Cana

Wed 1/22

2:02 pm-10:20 pm

1 stop10h 18m

$345

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 1/2

7:34 am-3:55 pm

2 stops30h 21m

Punta Cana

Mon 1/13

4:54 pm-4:14 pm

2 stops25h 20m

$406

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 1/5

12:58 pm-1:45 pm

1 stop23h 47m

Montego Bay Sangster Intl

Sat 1/11

2:49 pm-9:55 am

1 stop20h 06m

$445

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 1/9

4:08 pm-1:09 pm

2 stops44h 01m

Montego Bay Sangster Intl

Thu 1/16

11:44 am-6:01 pm

2 stops31h 17m

$448

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 12/9

6:00 am-2:04 pm

1 stop7h 04m

Montego Bay Sangster Intl

Fri 12/13

3:29 pm-10:06 pm

1 stop7h 37m

$468

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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 $335). 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 November 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 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 November 20, 2024.
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

KLM
7.8
Good
1,350 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $88. Southwest flights start at $105 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 $335). 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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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$365FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$199Average$277FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$275Average$717FlexibilityNo cancel feeOn-time63%
DeltaCheapest$365Average$686FlexibilityNo cancel feeOn-timeN/A
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