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$118+ Cheap flights from Caribbean Islands to Midway (MDW)

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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Midway

Keep the following information in mind while searching for Caribbean Islands to Midway flight deals. Data was last updated September 25, 2025.

Round-trip from

$227
(Southwest)

One-way from

$118
(Kiwi.com)
From Caribbean Islands to Chicago Midway
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One-way flight from Caribbean Islands to Chicago Midway
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Find flight deals from Caribbean Islands to Midway

Cheapest flights from Caribbean Islands to Midway
Explore the most affordable flight options available from Caribbean Islands to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2025.

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.
Thu 11/136:40 amSJU - MDW
1 stop6h 45mSouthwest
Mon 11/172:25 pmMDW - SJU
2 stops8h 10mSouthwest
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.
Fri 10/243:05 pmSJU - MDW
1 stop9h 41mFrontier
Fri 10/316:20 amMDW - SJU
1 stop6h 59mFrontier
Deal found 9/24$263
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:22 pmSJU - MDW
1 stop7h 25mFrontier
Sun 11/25:20 amMDW - SJU
1 stop6h 59mFrontier
Deal found 9/23$272
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:16 pmSJU - MDW
1 stop9h 25mFrontier
Mon 10/66:20 amMDW - SJU
1 stop6h 51mFrontier
Deal found 9/24$276
This Booking.com deal was found by Cheapflights users on 9/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:59 amSJU - MDW
1 stop22h 04mFrontier
Mon 10/276:15 amMDW - SJU
1 stop6h 51mFrontier
Deal found 9/22$279
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:22 pmSJU - MDW
1 stop10h 16mFrontier
Mon 12/83:20 pmMDW - SJU
1 stop7h 34mFrontier
Deal found 9/24$284
This Priceline deal was found by Cheapflights users on 9/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/81:26 pmSJU - MDW
1 stop18h 59mFrontier
Sun 10/125:20 amMDW - SJU
1 stop18h 48mFrontier
Deal found 9/22$290
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.
Fri 10/242:49 amSJU - MDW
1 stop8h 32mMultiple Airlines
Sun 11/25:40 amMDW - SJU
1 stop16h 38mMultiple Airlines
Deal found 9/25$291
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.
Thu 10/305:50 amSJU - MDW
2 stops8h 30mSouthwest
Sun 11/21:40 pmMDW - SJU
1 stop6h 05mSouthwest
Deal found 9/23$292
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:22 amSJU - MDW
2 stops18h 24mFrontier
Mon 10/2010:33 amMDW - SJU
1 stop8h 23mFrontier
Deal found 9/23$293
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.
Thu 11/64:19 pmSDQ - MDW
1 stop7h 44mFrontier
Wed 11/122:06 pmMDW - SDQ
1 stop22h 55mFrontier
Deal found 9/24$320
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.
Thu 12/44:35 pmAUA - MDW
2 stops18h 19mDelta
Mon 12/81:14 pmMDW - AUA
2 stops22h 41mDelta
Deal found 9/25$338

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Midway 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 25, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Chicago Midway Airport that are best for you.

Fly from

Caribbean Islands

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/15

2:45 pm-10:45 pm

1 stop9h 00m

Chicago Midway

Wed 10/29

12:30 pm-10:45 pm

1 stop9h 15m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/30

3:35 pm-9:50 pm

1 stop7h 15m

Chicago Midway

Sun 11/2

1:40 pm-9:45 pm

1 stop6h 05m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/25

4:22 pm-10:47 pm

1 stop7h 25m

Chicago Midway

Sun 11/2

5:20 am-2:19 pm

1 stop6h 59m

$272

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/2

3:16 pm-11:41 pm

1 stop9h 25m

Chicago Midway

Sun 10/5

6:21 am-3:22 pm

1 stop8h 01m

$276

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/8

4:14 pm-9:35 pm

1 stop7h 21m

Chicago Midway

Sat 11/15

6:15 am-3:19 pm

1 stop7h 04m

$276

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/31

5:40 am-1:00 pm

2 stops8h 20m

Chicago Midway

Mon 11/3

2:10 pm-12:35 am

2 stops8h 25m

$292

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/17

2:49 am-10:21 am

1 stop8h 32m

Chicago Midway

Mon 10/20

9:45 am-11:29 pm

1 stop12h 44m

$294

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/22

2:45 pm-10:45 pm

1 stop9h 00m

Chicago Midway

Wed 10/29

1:15 pm-11:50 pm

2 stops9h 35m

$311

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 11/13

6:40 am-3:50 pm

2 stops11h 10m

Chicago Midway

Mon 11/17

2:25 pm-12:35 am

2 stops8h 10m

$311

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Thu 12/4

3:10 pm-9:54 am

2 stops20h 44m

Chicago Midway

Sun 12/7

5:32 pm-1:55 pm

2 stops18h 23m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean Islands to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Caribbean Islands 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 Caribbean Islands to Chicago Midway Airport

What is the cheapest month to book a flight from Caribbean Islands to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Caribbean Islands to Chicago Midway Airport (average of $160). Flying from Caribbean Islands to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 EPX to MDW?

Find hourly flight availability from Caribbean Islands to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 25, 2025.

When flying from Caribbean Islands to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 25, 2025.
Read reviews from past customers who have flown Southwest from Caribbean Islands to Chicago Midway Airport. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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 Caribbean Islands to Midway. 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 Caribbean Islands to Chicago Midway Airport?

    There are many flights that can get you from Caribbean Islands to Chicago Midway Airport in 7h 25m. Fly via Southwest, Frontier, or Delta to get the fastest option. Airlines will cover a distance of 2057 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Caribbean Islands to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $132. Frontier flights start at $137 while deals on Delta start at $208 one-way.

  • What are the most popular routes from Caribbean Islands to Chicago Midway Airport?

    When deciding which route to take from Caribbean Islands to Chicago Midway Airport consider San Juan Luis Munoz Marin Intl - Chicago Midway, Santo Domingo Las Americas - Chicago Midway or Simpson Bay Princess Juliana - Chicago Midway as they are the most popular.

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

    The cheapest flight price from Caribbean Islands to Chicago Midway Airport is $191. On average you can expect to pay $231. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago Midway), can usually be booked for $227.

  • Can I find deals for flights from Caribbean Islands to Midway that include hotel bookings?

    Yes. In addition to deals on Caribbean Islands to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean Islands to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean Islands to Midway.

  • Can I find deals for business class flights from Caribbean Islands to Midway?

    Yes. Cheapflights offers flight deals from Caribbean Islands to Midway 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 Caribbean Islands to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Caribbean Islands to Chicago Midway Airport (average of $160). Flying from Caribbean Islands to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Caribbean Islands to Midway

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Top 2 airlines flying from Caribbean Islands to Midway

Discover the top 2 airlines that operate flights from Caribbean Islands to Midway. 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 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$535FlexibilityNo cancel feeOn-time63%

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