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Midway

$121+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
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 August 11, 2025.

Round-trip from

$258
(Priceline)

One-way from

$121
(SmartFares)
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 August 11, 2025.

This Priceline deal was found by Cheapflights users on 8/11. 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.
Sat 10/184:18 pmSJU - MDW
1 stop8h 07mFrontier
Mon 10/206:20 amMDW - SJU
1 stop6h 49mFrontier
Deal found 8/11$258
This Cheapflightsfares deal was found by Cheapflights users on 8/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1712:28 amSJU - MDW
1 stop7h 43mFrontier
Sat 9/276:15 amMDW - SJU
1 stop6h 56mFrontier
Deal found 8/9$261
This Southwest deal was found by Cheapflights users on 8/11. 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 9/167:30 amMDW - SJU
1 stop6h 25mSouthwest
Deal found 8/11$263
This Cheapflightsfares deal was found by Cheapflights users on 8/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1712:28 amSJU - MDW
1 stop7h 43mFrontier
Thu 9/256:20 amMDW - SJU
1 stop6h 51mFrontier
Deal found 8/9$266
This Priceline deal was found by Cheapflights users on 8/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/43:16 pmSJU - MDW
1 stop9h 04mFrontier
Mon 9/86:20 amMDW - SJU
1 stop6h 51mFrontier
Deal found 8/9$268
This Frontier deal was found by Cheapflights users on 8/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:28 amSJU - MDW
1 stop7h 43mFrontier
Mon 10/66:20 amMDW - SJU
1 stop6h 51mFrontier
Deal found 8/9$271
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:28 amSJU - MDW
1 stop7h 43mFrontier
Sun 10/56:20 amMDW - SJU
1 stop6h 51mFrontier
Deal found 8/10$275
This Mytrip deal was found by Cheapflights users on 8/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/183:16 pmSJU - MDW
1 stop9h 04mFrontier
Thu 10/28:15 amMDW - SJU
1 stop14h 08mFrontier
Deal found 8/10$284
This Travelocity deal was found by Cheapflights users on 8/11. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1811:03 amBQN - MDW
2 stops13h 22mFrontier
Tue 10/218:05 amMDW - BQN
2 stops16h 59mFrontier
Deal found 8/11$329
This Delta deal was found by Cheapflights users on 8/11. 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 8/11$339
This Southwest deal was found by Cheapflights users on 8/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/82:50 pmPUJ - MDW
1 stop8h 35mSouthwest
Mon 9/155:10 amMDW - PUJ
1 stop7h 55mSouthwest
Deal found 8/9$399
This Delta deal was found by Cheapflights users on 8/11. 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 11/63:49 pmPUJ - MDW
1 stop8h 25mDelta
Mon 11/106:00 amMDW - PUJ
1 stop6h 23mDelta
Deal found 8/11$414

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 August 11, 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

Sat 10/18

4:18 pm-11:25 pm

1 stop8h 07m

Chicago Midway

Mon 10/20

6:20 am-2:09 pm

1 stop6h 49m

$258

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/17

12:28 am-7:11 am

1 stop7h 43m

Chicago Midway

Sat 9/27

6:15 am-2:11 pm

1 stop6h 56m

$261

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

7:30 am-2:55 pm

1 stop6h 25m

$263

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/17

12:28 am-7:11 am

1 stop7h 43m

Chicago Midway

Thu 9/25

6:20 am-2:11 pm

1 stop6h 51m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/4

3:16 pm-11:20 pm

1 stop9h 04m

Chicago Midway

Mon 9/8

6:20 am-2:11 pm

1 stop6h 51m

$268

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/1

12:28 am-7:11 am

1 stop7h 43m

Chicago Midway

Mon 10/6

6:20 am-2:11 pm

1 stop6h 51m

$271

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/1

12:28 am-7:11 am

1 stop7h 43m

Chicago Midway

Sun 10/5

6:20 am-2:11 pm

1 stop6h 51m

$275

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/18

3:16 pm-11:20 pm

1 stop9h 04m

Chicago Midway

Thu 10/2

8:15 am-11:23 pm

1 stop14h 08m

$284

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sat 10/18

11:03 am-11:25 pm

2 stops13h 22m

Chicago Midway

Tue 10/21

8:05 am-2:04 am

2 stops16h 59m

$329

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

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 August 11, 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 August 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and WestJet 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

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
7,978 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
3,007 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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.
Frontier
5.8
Fair
3,222 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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 Islands 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 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 Nassau Intl - 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 $208. On average you can expect to pay $256. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago Midway), can usually be booked for $296.

  • 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
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean Islands 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 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$504FlexibilityNo cancel feeOn-time63%

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