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Midway

$117+ Cheap flights from Caribbean 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
out 16 — out 231
qui 10/16
qui 10/23
1 adult, Economy
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Cheap flight deals from Caribbean to Midway

Keep the following information in mind while searching for Caribbean to Midway flight deals. Data was last updated setembro 16, 2025.

Round-trip from

$227
(Southwest)

One-way from

$117
(Trip.com)

Popular in

August

Cheapest in

January

Average price

$297

Good one-way deal

$231 or less
From Caribbean to Chicago Midway
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One-way flight from Caribbean to Chicago Midway
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Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Caribbean to Chicago Midway.
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Find flight deals from Caribbean to Midway

Cheapest flights from Caribbean to Midway
Explore the most affordable flight options available from Caribbean to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on setembro 16, 2025.

This Frontier deal was found by Cheapflights users on 9/16. 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.
sáb 10/256:22 amSJU - MDW
2 stops17h 25mFrontier
sex 10/319:32 amMDW - SJU
1 stop10h 52mFrontier
Deal found 9/16$203
This Southwest deal was found by Cheapflights users on 9/16. 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.
qui 10/235:50 amSJU - MDW
2 stops8h 30mSouthwest
dom 10/266:55 amMDW - SJU
1 stop7h 55mSouthwest
Deal found 9/16$227
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
sex 10/243:05 pmSJU - MDW
1 stop9h 41mFrontier
sex 10/316:20 amMDW - SJU
1 stop6h 59mFrontier
Deal found 9/13$235
This Frontier deal was found by Cheapflights users on 9/14. 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.
qui 10/166:22 amSJU - MDW
2 stops18h 24mFrontier
seg 10/2010:33 amMDW - SJU
1 stop8h 23mFrontier
Deal found 9/14$244
This Frontier deal was found by Cheapflights users on 9/15. 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.
seg 10/69:26 pmSJU - MDW
2 stops17h 12mFrontier
sex 10/1710:33 amMDW - SJU
1 stop8h 23mFrontier
Deal found 9/15$249
This Frontier deal was found by Cheapflights users on 9/15. 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.
qui 12/43:00 pmSJU - MDW
1 stop10h 25mFrontier
seg 12/82:15 pmMDW - SJU
1 stop10h 35mFrontier
Deal found 9/15$251
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
sáb 11/156:00 amSJU - MDW
2 stops17h 35mMultiple Airlines
ter 11/186:26 pmMDW - SJU
1 stop31h 07mMultiple Airlines
Deal found 9/15$253
This Frontier deal was found by Cheapflights users on 9/15. 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.
qua 10/221:59 amSJU - MDW
2 stops19h 22mFrontier
dom 10/269:26 pmMDW - SJU
2 stops16h 58mFrontier
Deal found 9/15$255
This Frontier deal was found by Cheapflights users on 9/15. 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.
ter 9/239:26 pmSJU - MDW
2 stops19h 32mFrontier
sex 9/266:21 amMDW - SJU
1 stop8h 01mFrontier
Deal found 9/15$256
This Frontier deal was found by Cheapflights users on 9/14. 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.
sex 10/243:05 pmSJU - MDW
1 stop9h 41mFrontier
dom 10/269:26 pmMDW - SJU
2 stops16h 58mFrontier
Deal found 9/14$261
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
qua 10/291:59 amSJU - MDW
1 stop13h 34mFrontier
seg 11/36:20 amMDW - SJU
1 stop6h 59mFrontier
Deal found 9/13$262
This Priceline deal was found by Cheapflights users on 9/15. 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.
qua 10/152:59 amBQN - MDW
1 stop8h 47mFrontier
sáb 10/1811:31 amMDW - BQN
1 stop13h 33mFrontier
Deal found 9/15$286

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 setembro 16, 2025.
Use the filters below to find and compare flights from Caribbean to Chicago Midway Airport that are best for you.

Fly from

Caribbean

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

ter 10/21

2:45 pm-10:45 pm

1 stop9h 00m

Chicago Midway

seg 10/27

9:45 am-9:55 pm

1 stop11h 10m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qui 10/23

5:50 am-1:20 pm

2 stops8h 30m

Chicago Midway

dom 10/26

6:55 am-3:50 pm

1 stop7h 55m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qui 10/9

1:05 pm-9:55 pm

1 stop9h 50m

Chicago Midway

sex 10/17

5:50 pm-9:50 am

2 stops15h 00m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qui 10/23

5:50 am-2:20 pm

1 stop9h 30m

Chicago Midway

qua 10/29

9:15 am-8:45 pm

1 stop10h 30m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qui 10/30

5:50 am-1:20 pm

2 stops8h 30m

Chicago Midway

dom 11/2

1:40 pm-9:45 pm

1 stop6h 05m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qui 10/23

3:19 pm-11:46 pm

1 stop9h 27m

Chicago Midway

seg 10/27

9:45 am-11:29 pm

1 stop12h 44m

$276

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

qua 10/15

2:59 am-10:46 am

1 stop8h 47m

Chicago Midway

sáb 10/18

11:31 am-2:04 am

1 stop13h 33m

$286

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

qua 10/22

2:59 am-11:46 pm

2 stops21h 47m

Chicago Midway

qui 10/30

6:20 am-2:17 am

2 stops18h 57m

$303

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

ter 11/4

9:40 am-7:25 pm

1 stop11h 45m

Chicago Midway

dom 11/9

1:25 pm-12:35 am

2 stops9h 10m

$311

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

sex 10/17

5:50 am-2:20 pm

1 stop9h 30m

Chicago Midway

ter 10/21

6:55 am-5:15 pm

1 stop9h 20m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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

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

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

Currently, April is the cheapest month in which you can book a flight from Caribbean to Chicago Midway Airport (average of $160). Flying from Caribbean 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 CB to MDW?

Find hourly flight availability from Caribbean 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 setembro 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean to Chicago Midway Airport as you normally would.

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 setembro 16, 2025.
Read reviews from past customers who have flown Southwest and Frontier from Caribbean to Chicago Midway Airport. 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
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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 Caribbean 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 to Chicago Midway Airport?

    Southwest, Frontier, and Delta can get you from Caribbean to Chicago Midway Airport in just under 8h 18m. Your travel time can differ by up to 42m. The distance between Caribbean and Chicago Midway Airport is about 1932 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airlines for a one-way flight from Caribbean to Chicago Midway Airport are Frontier ($142), Southwest ($174), and Delta ($200).

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

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

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

    Looking for the cheapest flight from Caribbean to Chicago Midway Airport? While on average our users pay $231, our data indicates the cheapest price to be $191. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $227.

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

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

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

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Caribbean to Midway

Discover the top 2 airlines that operate flights from Caribbean 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 setembro 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$320Average$524FlexibilityNo cancel feeOn-time63%

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