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$113+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$237
(Frontier)

One-way from

$113
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$301

Good round-trip deal

$460 or less

Good one-way deal

$164 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. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Caribbean to Chicago Midway.
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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 July 30, 2025.

This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/13:21 pmSJU - MDW
1 stop8h 48mFrontier
Sat 11/156:10 amMDW - SJU
1 stop7h 05mFrontier
Deal found 7/29$234
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/62:59 amBQN - MDW
1 stop18h 23mFrontier
Thu 8/149:12 pmMDW - BQN
1 stop12h 34mFrontier
Deal found 7/29$288
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/113:19 pmSJU - MDW
3 stops26h 24mMultiple Airlines
Mon 9/1512:50 pmMDW - SJU
3 stops31h 06mMultiple Airlines
Deal found 7/30$321
This Delta deal was found by Cheapflights users on 7/29. 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 10/22:35 pmMBJ - MDW
1 stop7h 01mDelta
Mon 10/66:00 amMDW - MBJ
1 stop9h 34mDelta
Deal found 7/29$339
This Southwest deal was found by Cheapflights users on 7/29. 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 10/212:50 pmMBJ - MDW
2 stops7h 50mSouthwest
Mon 10/65:00 amMDW - MBJ
1 stop8h 55mSouthwest
Deal found 7/29$348
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 9/51:10 pmPUJ - MDW
1 stop9h 16mDelta
Sun 9/146:00 amMDW - PUJ
1 stop7h 32mDelta
Deal found 7/30$350
This Southwest deal was found by Cheapflights users on 7/30. 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 9/111:20 pmSJU - MDW
1 stop10h 10mSouthwest
Tue 9/169:00 amMDW - SJU
2 stops9h 45mSouthwest
Deal found 7/30$351
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/139:05 amMBJ - MDW
1 stop28h 42mFrontier
Wed 10/158:00 amMDW - MBJ
1 stop23h 53mFrontier
Deal found 7/29$359
This Delta deal was found by Cheapflights users on 7/30. 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 10/412:58 pmSJU - MDW
1 stop9h 12mDelta
Tue 10/76:00 amMDW - SJU
1 stop6h 19mDelta
Deal found 7/30$361
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/51:48 amSDQ - MDW
1 stop9h 52mFrontier
Tue 8/1211:39 amMDW - SDQ
1 stop11h 53mFrontier
Deal found 7/30$380
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:22 pmPUJ - MDW
1 stop8h 47mFrontier
Sat 10/186:10 amMDW - PUJ
1 stop6h 57mFrontier
Deal found 7/29$391
This Southwest deal was found by Cheapflights users on 7/29. 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 8/282:50 pmPUJ - MDW
1 stop8h 35mSouthwest
Thu 9/45:10 amMDW - PUJ
1 stop7h 55mSouthwest
Deal found 7/29$399

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 July 30, 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

Sat 11/1

3:21 pm-11:09 pm

1 stop8h 48m

Chicago Midway

Sat 11/15

6:10 am-3:15 pm

1 stop7h 05m

$234

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Wed 8/6

2:59 am-8:22 pm

1 stop18h 23m

Chicago Midway

Thu 8/14

9:12 pm-10:46 am

1 stop12h 34m

$288

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

3:19 pm-4:43 pm

3 stops26h 24m

Chicago Midway

Mon 9/15

12:50 pm-8:56 pm

3 stops31h 06m

$321

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/2

2:35 pm-9:36 pm

1 stop7h 01m

Chicago Midway

Mon 10/6

6:00 am-3:34 pm

1 stop9h 34m

$339

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/2

12:50 pm-8:40 pm

2 stops7h 50m

Chicago Midway

Mon 10/6

5:00 am-1:55 pm

1 stop8h 55m

$348

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 9/5

1:10 pm-9:26 pm

1 stop9h 16m

Chicago Midway

Sun 9/14

6:00 am-2:32 pm

1 stop7h 32m

$350

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

1:20 pm-10:30 pm

1 stop10h 10m

Chicago Midway

Tue 9/16

7:40 am-7:45 pm

1 stop11h 05m

$351

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/13

9:05 am-1:47 pm

1 stop28h 42m

Chicago Midway

Wed 10/15

8:00 am-7:53 am

1 stop23h 53m

$359

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/4

12:58 pm-9:10 pm

1 stop9h 12m

Chicago Midway

Tue 10/7

6:00 am-1:19 pm

1 stop6h 19m

$361

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 10/11

3:22 pm-11:09 pm

1 stop8h 47m

Chicago Midway

Sat 10/25

6:10 am-2:07 pm

1 stop6h 57m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 54 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 July 30, 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 July 30, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Air Transat 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
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Air Transat
7.7
Good
424 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
LATAM Airlines
7.5
Good
1,822 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
WestJet
7.2
Good
2,975 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 ($113), Southwest ($176), and Delta ($192).

  • 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 $256, our data indicates the cheapest price to be $162. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $259.

  • 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
Valparaiso
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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$504FlexibilityNo cancel feeOn-time63%

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