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Caribbean Islands

$113+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
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 November 10, 2025.

Round-trip from

$216
(CheapOair)

One-way from

$113
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$432
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. 11% potential increase in price ($50 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 November 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 November 10, 2025.

This CheapOair deal was found by Cheapflights users on 11/10. 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 12/112:16 pmMDW - SJU
1 stop18h 16mFrontier
Thu 12/184:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 11/10$216
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/77:44 amMDW - SJU
1 stop30h 29mFrontier
Sat 12/131:59 amSJU - MDW
2 stops35h 09mFrontier
Deal found 11/9$221
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 12/313:32 pmMDW - SJU
1 stop9h 07mFrontier
Thu 1/87:01 pmSJU - MDW
1 stop20h 08mFrontier
Deal found 11/8$225
This Frontier deal was found by Cheapflights users on 11/8. 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 12/83:10 pmMDW - SJU
1 stop9h 40mFrontier
Mon 12/154:31 pmSJU - MDW
1 stop7h 41mFrontier
Deal found 11/8$226
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 11/265:57 pmMDW - SJU
1 stop13h 43mFrontier
Wed 12/39:15 amSJU - MDW
1 stop29h 46mFrontier
Deal found 11/9$244
This Frontier deal was found by Cheapflights users on 11/8. 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 12/53:52 pmMDW - SJU
1 stop8h 58mFrontier
Fri 12/124:31 pmSJU - MDW
1 stop7h 41mFrontier
Deal found 11/8$246
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/112:16 pmMDW - SJU
1 stop18h 16mFrontier
Sun 12/141:59 amSJU - MDW
2 stops22h 19mFrontier
Deal found 11/9$250
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/47:23 pmMDW - SJU
2 stops27h 22mMultiple Airlines
Wed 12/107:10 amSJU - MDW
1 stop31h 51mMultiple Airlines
Deal found 11/9$253
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 11/2212:25 pmMDW - SJU
1 stop25h 35mFrontier
Wed 11/2610:40 amSJU - MDW
1 stop8h 17mFrontier
Deal found 11/7$255
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/76:37 pmMDW - STT
1 stop18h 12mMultiple Airlines
Thu 12/183:23 pmSTT - MDW
1 stop8h 35mMultiple Airlines
Deal found 11/9$322
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 12/62:59 pmMDW - PUJ
1 stop25h 39mMultiple Airlines
Sat 12/139:38 amPUJ - MDW
1 stop14h 52mMultiple Airlines
Deal found 11/8$326
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 12/128:42 pmMDW - PUJ
1 stop16h 14mFrontier
Fri 12/193:39 pmPUJ - MDW
2 stops31h 25mFrontier
Deal found 11/7$329

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 November 10, 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

Mon 1/19

10:46 am-11:44 pm

1 stop10h 58m

San Juan Luis Munoz Marin Intl

Fri 1/23

7:30 am-12:01 pm

1 stop6h 31m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

10:46 am-11:44 pm

1 stop10h 58m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:26 pm

1 stop8h 31m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

12:48 pm-11:44 pm

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:26 pm

1 stop8h 31m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/29

3:15 pm-12:35 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Tue 2/3

9:05 am-2:45 pm

1 stop7h 40m

$226

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/31

12:15 pm-11:00 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:10 am-1:55 pm

2 stops9h 45m

$246

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/3

2:20 pm-12:35 am

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Fri 2/6

4:10 pm-10:25 pm

1 stop8h 15m

$252

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

12:15 pm-11:00 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:00 am-1:20 pm

2 stops9h 20m

$265

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/7

12:45 pm-12:10 am

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Wed 2/11

9:05 am-6:35 pm

1 stop11h 30m

$282

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

9:50 am-8:55 pm

2 stops9h 05m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:00 am-12:30 pm

2 stops8h 30m

$290

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/31

6:00 am-3:30 pm

1 stop7h 30m

Punta Cana

Sat 2/7

3:45 pm-10:26 pm

1 stop8h 41m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean Islands (average of $126). Flying from Chicago Midway Airport to Caribbean Islands in June is currently the most expensive (average of $298). 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 November 10, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Caribbean Islands in the evening. If you’re flexible enough to do this you can expect to save up to 44% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Chicago Midway Airport to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Midway to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to Caribbean Islands flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 10, 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
4,236 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

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
7.9
Good
8,003 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

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
3,111 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

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 3h 38m. Airlines will cover a distance of 2057 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 Delta, with whom users have recently found tickets for as low as $113. However, be on the lookout for offers from Southwest and Frontier, 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 - Oranjestad Reina Beatrix.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean Islands (average of $126). Flying from Chicago Midway Airport to Caribbean Islands in June is currently the most expensive (average of $298). 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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$375FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$327FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$671FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$380Average$700FlexibilityNo cancel feeOn-time63%

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