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Caribbean Islands

$116+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
1 adult, Economy
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Cheap flight deals from Midway to Caribbean Islands

Keep the following information in mind while searching for Midway to Caribbean Islands flight deals. Data was last updated April 4, 2025.

Round-trip from

$298
(CheapOair)

One-way from

$116
(Southwest)

Popular in

December

Cheapest in

August

Average price

$312
From Chicago Midway to Caribbean Islands
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One-way flight from Chicago Midway to Caribbean Islands
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Highest demand for flights based on searches. 15% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 4, 2025.

This CheapOair deal was found by Cheapflights users on 4/4. 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.
Sun 4/132:16 pmMDW - SJU
1 stop18h 29mFrontier
Fri 4/182:20 pmSJU - MDW
1 stop26h 55mFrontier
Deal found 4/4$298
This Delta deal was found by Cheapflights users on 4/4. 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 5/56:04 amMDW - PUJ
1 stop7h 26mDelta
Wed 5/141:05 pmPUJ - MDW
1 stop9h 23mDelta
Deal found 4/4$335
This Southwest deal was found by Cheapflights users on 4/2. 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.
Sat 4/266:35 amMDW - SJU
1 stop11h 15mSouthwest
Sat 5/31:00 pmSJU - MDW
Nonstop5h 20mSouthwest
Deal found 4/2$377
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/1312:46 pmMDW - PUJ
1 stop21h 58mMultiple Airlines
Fri 4/1812:39 pmPUJ - MDW
1 stop8h 16mMultiple Airlines
Deal found 4/3$387
This Delta deal was found by Cheapflights users on 4/3. 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 9/610:35 amMDW - SJU
1 stop10h 37mDelta
Sat 9/137:30 amSJU - MDW
1 stop11h 28mDelta
Deal found 4/3$420
This Frontier deal was found by Cheapflights users on 4/4. 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.
Mon 5/269:12 pmMDW - PUJ
1 stop12h 38mFrontier
Sat 5/3112:00 pmPUJ - MDW
1 stop9h 17mFrontier
Deal found 4/4$421
This Frontier deal was found by Cheapflights users on 4/4. 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 5/309:12 pmMDW - SXM
1 stop13h 12mFrontier
Sat 6/1412:36 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 4/4$431
This Delta deal was found by Cheapflights users on 4/4. 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 5/46:04 amMDW - SDQ
1 stop6h 11mDelta
Sat 5/107:05 amSDQ - MDW
2 stops15h 09mDelta
Deal found 4/4$456
This Booking.com deal was found by Cheapflights users on 4/4. 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.
Thu 5/158:30 amMDW - MBJ
1 stop28h 11mFrontier
Sun 5/182:07 pmMBJ - MDW
1 stop23h 27mFrontier
Deal found 4/4$458
This Delta deal was found by Cheapflights users on 4/4. 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 4/296:04 amMDW - MBJ
1 stop9h 27mDelta
Sat 5/311:28 amMBJ - MDW
1 stop6h 52mDelta
Deal found 4/4$470
This Delta deal was found by Cheapflights users on 4/3. 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.
Wed 5/286:00 amMDW - STT
1 stop8h 10mDelta
Wed 6/42:51 pmSTT - MDW
1 stop7h 36mDelta
Deal found 4/3$479
This CheapOair deal was found by Cheapflights users on 4/4. 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.
Sat 7/196:00 amMDW - AUA
1 stop7h 20mFrontier
Sat 7/263:35 pmAUA - MDW
1 stop8h 46mFrontier
Deal found 4/4$488

Cheapflights Fare Finder

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 April 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Caribbean Islands that are best for you.

Fly from

Midway

Fly to

Caribbean Islands

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 4/13

2:16 pm-9:45 am

1 stop18h 29m

San Juan Luis Munoz Marin Intl

Fri 4/18

2:20 pm-4:15 pm

1 stop26h 55m

$298

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 5/5

6:04 am-2:30 pm

1 stop7h 26m

Punta Cana

Wed 5/14

1:05 pm-9:28 pm

1 stop9h 23m

$335

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 4/26

6:35 am-6:50 pm

1 stop11h 15m

San Juan Luis Munoz Marin Intl

Sat 5/3

1:00 pm-5:20 pm

Nonstop5h 20m

$377

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 5/9

1:19 pm-11:47 am

1 stop21h 28m

Punta Cana

Tue 5/13

3:22 pm-11:26 am

2 stops21h 04m

$398

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 5/13

6:00 am-4:31 pm

1 stop9h 31m

San Juan Luis Munoz Marin Intl

Wed 6/4

12:50 pm-9:27 pm

1 stop9h 37m

$418

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 5/26

9:12 pm-10:50 am

1 stop12h 38m

Punta Cana

Sat 5/31

12:00 pm-8:17 pm

1 stop9h 17m

$421

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$431

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 5/4

6:04 am-1:15 pm

1 stop6h 11m

Santo Domingo Las Americas

Sat 5/10

7:05 am-9:14 pm

2 stops15h 09m

$456

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 5/15

8:30 am-12:41 pm

1 stop28h 11m

Montego Bay Sangster Intl

Sun 5/18

2:07 pm-1:34 pm

1 stop23h 27m

$458

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 4/29

6:04 am-3:31 pm

1 stop9h 27m

Montego Bay Sangster Intl

Sat 5/3

11:28 am-6:20 pm

1 stop6h 52m

$470

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

Showing 1-10 of 58 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Caribbean Islands

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 December is currently the most expensive (average of $336). 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 April 4, 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 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 April 4, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and LATAM Airlines 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
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,901 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
LATAM Airlines
7.5
Good
1,752 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,795 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,276 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 Southwest, with whom users have recently found tickets for as low as $116. However, be on the lookout for offers from Frontier 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.

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

    Looking at all options, your cheapest flight can be booked for $288. While the most popular route (Chicago Midway - San Juan Luis Munoz Marin Intl) can be booked for $289 on average our data indicates $358 when flying from Chicago Midway Airport to Caribbean Islands.

  • 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 December is currently the most expensive (average of $336). 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.

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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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$133Average$376FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$174Average$278FlexibilityNo cancel feeOn-time65%
DeltaCheapest$325Average$758FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$342Average$711FlexibilityNo cancel feeOn-time63%

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