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$82+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Round-trip from

$160
(Priceline)

One-way from

$82
(Vakatrip)
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 January 21, 2025.

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/37:15 amMDW - SJU
1 stop15h 24mFrontier
Fri 2/76:00 amSJU - MDW
1 stop8h 09mFrontier
Deal found 1/20$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.
Sun 2/21:20 pmMDW - SJU
2 stops9h 30mSouthwest
Fri 2/71:45 pmSJU - MDW
1 stop10h 15mSouthwest
Deal found 1/20$235
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/12:36 pmMDW - PUJ
1 stop18h 42mFrontier
Mon 4/72:49 pmPUJ - MDW
1 stop10h 01mFrontier
Deal found 1/20$294
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/2810:57 amMDW - SJU
1 stop10h 49mDelta
Thu 1/304:15 pmSJU - MDW
1 stop8h 05mDelta
Deal found 1/20$325
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/256:00 amMDW - PUJ
1 stop7h 25mDelta
Thu 2/274:50 pmPUJ - MDW
1 stop7h 30mDelta
Deal found 1/20$355
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/276:00 amMDW - PUJ
1 stop7h 25mKLM
Wed 2/54:50 pmPUJ - MDW
1 stop7h 30mKLM
Deal found 1/20$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.
Fri 2/216:48 pmMDW - PUJ
1 stop13h 52mMultiple Airlines
Tue 2/254:48 pmPUJ - MDW
2 stops16h 19mMultiple Airlines
Deal found 1/20$398
This FlightHub deal was found by Cheapflights users on 1/19. 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.
Wed 2/191:16 pmMDW - SDQ
2 stops23h 24mFrontier
Mon 2/242:36 pmSDQ - MDW
2 stops26h 37mFrontier
Deal found 1/19$401
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Sat 2/227:10 pmMDW - SDQ
2 stops15h 58mMultiple Airlines
Tue 2/2510:00 amSDQ - MDW
1 stop7h 13mMultiple Airlines
Deal found 1/19$403
This Delta deal was found by Cheapflights users on 1/19. 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.
Sun 1/266:00 amMDW - SDQ
1 stop5h 57mDelta
Fri 1/313:22 pmSDQ - MDW
1 stop8h 58mDelta
Deal found 1/19$417
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/48:30 amMDW - MBJ
1 stop28h 31mFrontier
Thu 5/82:21 pmMBJ - MDW
1 stop9h 18mFrontier
Deal found 1/20$424
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.
Tue 1/285:31 pmMDW - MBJ
2 stops17h 39mMultiple Airlines
Thu 1/3011:44 amMBJ - MDW
1 stop7h 42mMultiple Airlines
Deal found 1/20$458

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/3

7:15 am-12:39 am

1 stop15h 24m

San Juan Luis Munoz Marin Intl

Fri 2/7

6:00 am-12:09 pm

1 stop8h 09m

$160

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

Fri 2/7

1:45 pm-10:00 pm

1 stop10h 15m

$235

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 4/1

2:36 pm-10:18 am

1 stop18h 42m

Punta Cana

Mon 4/7

2:49 pm-11:50 pm

1 stop10h 01m

$294

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 5/6

10:10 am-7:39 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Wed 5/14

6:15 am-2:54 pm

1 stop9h 39m

$325

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 2/25

6:00 am-3:25 pm

1 stop7h 25m

Punta Cana

Thu 2/27

4:50 pm-10:20 pm

1 stop7h 30m

$355

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 2/4

5:31 pm-3:54 pm

2 stops20h 23m

Santo Domingo Las Americas

Sat 2/15

9:00 am-6:15 pm

1 stop11h 15m

$393

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 2/21

6:48 pm-10:40 am

1 stop13h 52m

Punta Cana

Tue 2/25

4:48 pm-7:07 am

2 stops16h 19m

$398

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 2/19

1:16 pm-2:40 pm

2 stops23h 24m

Santo Domingo Las Americas

Mon 2/24

2:36 pm-3:13 pm

2 stops26h 37m

$401

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Fri 2/28

6:00 am-1:57 pm

1 stop5h 57m

Santo Domingo Las Americas

Wed 3/5

3:22 pm-10:20 pm

1 stop8h 58m

$417

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/4

8:30 am-1:01 pm

1 stop28h 31m

Montego Bay Sangster Intl

Thu 5/8

2:21 pm-11:39 pm

1 stop9h 18m

$424

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 $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 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 January 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 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 January 21, 2025.
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

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
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

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
4,659 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

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
4,659 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

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.

Air Transat
7.8
Good
381 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

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
4,659 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

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 $82. Southwest flights start at $118 while deals on Delta start at $163 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 $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.

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 2,558,603 searches. Data last updated January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$397FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$199Average$284FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$317Average$692FlexibilityNo cancel feeOn-time63%
DeltaCheapest$354Average$761FlexibilityNo cancel feeOn-timeN/A
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