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Caribbean Islands

$109+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Oct 26 — Nov 21
Sun 10/26
Sun 11/2
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 September 26, 2025.

Round-trip from

$226
(Kiwi.com)

One-way from

$109
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$380
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. 8% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/25. 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 10/235:56 pmMDW - SJU
1 stop20h 28mFrontier
Thu 10/309:00 amSJU - MDW
1 stop15h 25mFrontier
Deal found 9/25$226
This Southwest deal was found by Cheapflights users on 9/23. 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.
Fri 10/248:45 pmMDW - SJU
1 stop12h 05mSouthwest
Wed 10/292:45 pmSJU - MDW
1 stop9h 00mSouthwest
Deal found 9/23$227
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Mon 10/209:45 amMDW - SJU
1 stop12h 44mFrontier
Fri 10/2411:48 amSJU - MDW
2 stops12h 32mFrontier
Deal found 9/24$247
This eDestinos deal was found by Cheapflights users on 9/25. 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.
Mon 10/209:45 amMDW - SJU
1 stop12h 44mFrontier
Thu 10/239:06 pmSJU - MDW
1 stop15h 11mFrontier
Deal found 9/25$256
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Fri 10/316:20 amMDW - SJU
1 stop6h 59mFrontier
Fri 11/74:31 pmSJU - MDW
1 stop7h 37mFrontier
Deal found 9/23$263
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 10/281:56 pmMDW - SJU
2 stops26h 58mFrontier
Tue 11/49:00 amSJU - MDW
1 stop16h 55mFrontier
Deal found 9/25$264
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Wed 10/158:05 amMDW - SJU
2 stops16h 57mFrontier
Wed 10/224:51 pmSJU - MDW
1 stop31h 34mFrontier
Deal found 9/24$265
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Fri 10/1712:13 pmMDW - SJU
2 stops10h 16mFrontier
Tue 10/216:22 amSJU - MDW
1 stop18h 03mFrontier
Deal found 9/24$269
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Wed 10/292:06 pmMDW - SDQ
1 stop22h 50mFrontier
Sun 11/24:19 pmSDQ - MDW
1 stop28h 20mFrontier
Deal found 9/24$330
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 11/1511:36 amMDW - STT
1 stop25h 35mMultiple Airlines
Wed 11/194:06 pmSTT - MDW
1 stop26h 24mMultiple Airlines
Deal found 9/25$334
This Delta deal was found by Cheapflights users on 9/25. 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 11/106:00 amMDW - PUJ
1 stop7h 38mDelta
Fri 11/145:03 pmPUJ - MDW
1 stop8h 37mDelta
Deal found 9/25$337
This Delta deal was found by Cheapflights users on 9/25. 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 11/84:23 pmMDW - PUJ
2 stops19h 03mDelta
Fri 11/145:03 pmPUJ - MDW
1 stop8h 37mDelta
Deal found 9/25$342

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 September 26, 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 1/18

6:00 am-5:19 pm

1 stop9h 19m

San Juan Luis Munoz Marin Intl

Fri 1/23

2:10 pm-9:46 pm

1 stop9h 36m

$263

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 11/10

6:00 am-3:38 pm

1 stop7h 38m

Punta Cana

Sat 11/15

3:40 pm-9:01 am

1 stop19h 21m

$337

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 11/10

6:00 am-3:38 pm

1 stop7h 38m

Punta Cana

Fri 11/14

5:03 pm-11:40 pm

1 stop8h 37m

$337

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 10/29

12:35 pm-11:50 pm

2 stops10h 15m

San Juan Luis Munoz Marin Intl

Mon 11/3

9:40 am-7:25 pm

1 stop11h 45m

$351

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 11/1

1:45 pm-11:45 pm

2 stops9h 00m

San Juan Luis Munoz Marin Intl

Tue 11/4

5:45 am-1:45 pm

2 stops10h 00m

$351

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 11/16

6:00 am-4:18 pm

1 stop8h 18m

Punta Cana

Thu 11/20

5:43 pm-11:40 pm

1 stop7h 57m

$351

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 12/15

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Fri 12/19

1:50 pm-11:32 pm

1 stop10h 42m

$352

ChicagoNassau

MDW - NAS

MDWNAS

Chicago Midway

Mon 12/1

6:00 am-11:54 am

1 stop4h 54m

Nassau Intl

Thu 12/4

2:55 pm-11:32 pm

1 stop9h 37m

$353

ChicagoNassau

MDW - NAS

MDWNAS

Chicago Midway

Mon 12/1

6:00 am-11:54 am

1 stop4h 54m

Nassau Intl

Fri 12/5

4:53 pm-11:32 pm

1 stop7h 39m

$353

ChicagoNassau

MDW - NAS

MDWNAS

Chicago Midway

Mon 12/22

10:08 am-9:44 pm

1 stop10h 36m

Nassau Intl

Tue 12/30

8:10 am-4:15 pm

1 stop9h 05m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

Showing 1-10 of 60 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 June is currently the most expensive (average of $339). 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 September 26, 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.

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 September 26, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Caribbean Islands, such as Southwest, Delta, and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,161 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago Midway Airport to Caribbean Islands?

    Airlines like Delta, Southwest, and Frontier fly from Chicago Midway Airport to Caribbean Islands in about 7h 20m. The time it takes to get you to your destination can typically vary by up to 2h 55m. Airlines will cover a distance of 2189 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $114. 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.

  • 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 June is currently the most expensive (average of $339). 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Midway to Caribbean Islands

Discover the top 5 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 September 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$372FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$365FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$650FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$374Average$678FlexibilityNo cancel feeOn-time63%

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