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$64+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Oct 29 — Nov 51
Tue 10/29
Tue 11/5
1 adult, Economy
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MDW - SJU
Oct 29 - Nov 5

Find cheap flights from Midway to Caribbean with Cheapflights

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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 October 24, 2024.

This CheapOair deal was found by Cheapflights users on 10/23. 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.
Thu 11/71:58 pmMDW - SJU
1 stop28h 44mFrontier
Thu 11/141:38 pmSJU - MDW
1 stop11h 42mFrontier
Deal found 10/23$165
This eDestinos deal was found by Cheapflights users on 10/23. 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 11/241:31 pmMDW - SJU
2 stops28h 18mMultiple Airlines
Sun 12/89:49 pmSJU - MDW
1 stop14h 32mMultiple Airlines
Deal found 10/23$275
This Delta deal was found by Cheapflights users on 10/24. 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 - PUJ
1 stop8h 24mDelta
Thu 12/122:05 pmPUJ - MDW
1 stop10h 01mDelta
Deal found 10/24$343
This Frontier deal was found by Cheapflights users on 10/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/64:27 pmMDW - PUJ
2 stops16h 14mFrontier
Fri 12/132:30 pmPUJ - MDW
2 stops11h 50mFrontier
Deal found 10/23$347
This Southwest deal was found by Cheapflights users on 10/23. 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.
Wed 11/2011:55 amMDW - SJU
2 stops10h 50mSouthwest
Mon 11/254:45 pmSJU - MDW
1 stop8h 35mSouthwest
Deal found 10/23$374
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Sun 11/176:00 amMDW - MBJ
1 stop8h 52mMultiple Airlines
Sun 11/242:38 pmMBJ - MDW
2 stops18h 17mMultiple Airlines
Deal found 10/24$379
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Sun 11/172:51 pmMDW - PUJ
2 stops22h 55mMultiple Airlines
Sat 11/232:50 pmPUJ - MDW
1 stop10h 19mMultiple Airlines
Deal found 10/23$399
This Mytrip deal was found by Cheapflights users on 10/23. 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.
Thu 11/146:00 amMDW - MBJ
1 stop8h 52mFrontier
Sun 11/175:12 pmMBJ - MDW
1 stop22h 55mFrontier
Deal found 10/23$401
This Trip.com deal was found by Cheapflights users on 10/22. 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 10/286:43 pmMDW - STT
1 stop17h 18mMultiple Airlines
Thu 10/311:55 pmSTT - MDW
2 stops11h 08mMultiple Airlines
Deal found 10/22$413
This SmartFares deal was found by Cheapflights users on 10/23. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/176:49 pmMDW - SDQ
1 stop16h 16mFrontier
Mon 12/231:03 pmSDQ - MDW
1 stop10h 01mFrontier
Deal found 10/23$416
This Delta deal was found by Cheapflights users on 10/23. 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.
Sat 11/210:49 amMDW - SJU
1 stop10h 32mDelta
Sat 11/98:00 amSJU - MDW
1 stop11h 24mDelta
Deal found 10/23$419
This Delta deal was found by Cheapflights users on 10/24. 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 11/1210:41 amMDW - SDQ
2 stops12h 48mDelta
Tue 12/104:21 pmSDQ - MDW
1 stop7h 45mDelta
Deal found 10/24$420

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 2,462,889 searches. Data last updated October 24, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$128 - $924

Route

Depart

Return

Price

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 11/9

1 stop11h 55m

San Juan Luis Munoz Marin Intl

Sat 11/16

1 stop13h 04m

$128

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sun 11/24

2 stops28h 18m

San Juan Luis Munoz Marin Intl

Sun 12/8

1 stop14h 32m

$275

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/12

2 stops18h 56m

Punta Cana

Sat 1/18

1 stop13h 33m

$297

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 12/6

1 stop18h 02m

Montego Bay Sangster Intl

Tue 12/10

1 stop22h 25m

$328

Chicago MidwaySanto Domingo Las Americas

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 1/8

2 stops20h 14m

Santo Domingo Las Americas

Tue 2/25

2 stops25h 42m

$328

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 12/9

1 stop8h 24m

Punta Cana

Thu 12/12

1 stop10h 01m

$343

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 11/13

1 stop26h 53m

Montego Bay Sangster Intl

Sat 11/16

2 stops18h 49m

$348

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/11

1 stop8h 35m

San Juan Luis Munoz Marin Intl

Sat 1/18

Nonstop5h 15m

$370

Chicago MidwaySanto Domingo Las Americas

MDW - SDQ

MDWSDQ

Chicago Midway

Fri 1/31

1 stop6h 27m

Santo Domingo Las Americas

Wed 2/5

1 stop7h 54m

$395

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 11/17

2 stops22h 55m

Punta Cana

Sat 11/23

1 stop10h 19m

$399

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 12/2

3 stops28h 24m

Punta Cana

Wed 12/11

2 stops29h 32m

$834

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Sat 11/30

1 stop6h 52m

Simpson Bay Princess Juliana

Sat 12/7

1 stop8h 34m

$924

Flights are sorted by cheapest first

Deals found on 10/23

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 October 24, 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 October 24, 2024.
Southwest
8.1
Very good
5,150 reviews

Comfort

8.1

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,150 reviews
Southwest
8.1
Very good
5,150 reviews

Comfort

8.1

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,875 reviews
Southwest
8.1
Very good
5,150 reviews

Comfort

8.1

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Reviews

1 / 10

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

KLM
7.8
Good
1,351 reviews
Southwest
8.1
Very good
5,150 reviews

Comfort

8.1

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Reviews

1 / 10

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

WestJet
7.3
Good
2,806 reviews
Southwest
8.1
Very good
5,150 reviews

Comfort

8.1

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Reviews

1 / 10

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

Frontier
6.1
Okay
3,611 reviews
Southwest
8.1
Very good
5,150 reviews

Comfort

8.1

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

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.

  • Can I find flights from Chicago Midway Airport to Caribbean for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Caribbean for under $200. The cheapest flight booked recently is on Frontier for just $128, but on average you can expect to pay $407.

  • Are there nonstop flights from Chicago Midway Airport to Caribbean for under $900 on Cheapflights?

    Cheapflights has at least 3 direct flights from Chicago Midway Airport to Caribbean under $900. A good price for a nonstop flight from Chicago Midway Airport to Caribbean is less than $1,221.

  • Are there last-minute flights available from Chicago Midway Airport to Caribbean for under $300?

    There are currently 20+ open flights from Chicago Midway Airport to Caribbean within the next 7 days for less than $300.

  • 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 $64. Delta flights start at $160 while deals on Southwest start at $187 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.

  • What are the cheapest flights from Chicago Midway Airport to Caribbean?

    While on average a flight from Chicago Midway Airport to Caribbean is generally $510, our data shows the cheapest flight currently is $373. When looking at the most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), you can expect to pay $133 for that flight.

  • What does MDW to SJU mean?

    This is defined as Chicago Midway Airport (MDW) and San Juan Luis Munoz Marin Intl Airport (SJU). Codes like San Juan Luis Munoz Marin Intl Airport are often used to just call airports uniquely. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI).

  • Can I find deals for flights from Midway to Caribbean that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Caribbean flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Caribbean with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Caribbean flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Midway to Caribbean that allow pets onboard?

    Many airlines flying from Midway to Caribbean offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Caribbean?

    Yes, you can often find last-minute deals on Midway to Caribbean flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Caribbean flight deals updated?

    The Chicago Midway Airport to Caribbean flight deals you see on this page were last updated on 10/24.

  • 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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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 2,462,889 searches. Data last updated October 24, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$127Average$374FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$187Average$272FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$267Average$566FlexibilityNo cancel feeOn-time63%
DeltaCheapest$365Average$692FlexibilityNo cancel feeOn-timeN/A
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