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$68+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
1월 26 — 2월 21
일 1/26
일 2/2
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean Islands (zzEPX) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 1월 21, 2025.

Round-trip from

$144
(Trip.com)

One-way from

$70
(Priceline)
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 1월 21, 2025.

This Trip.com deal was found by Cheapflights users on 1/20. 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.
화 3/47:59 pmSJU - MDW
1 stop21h 14mFrontier
화 3/117:25 amMDW - SJU
1 stop25h 19mFrontier
Deal found 1/20$144
This Trip.com deal was found by Cheapflights users on 1/20. 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.
목 1/303:51 amBQN - MDW
1 stop12h 51mFrontier
일 2/210:58 amMDW - BQN
1 stop13h 48mFrontier
Deal found 1/20$254
This Southwest deal was found by Cheapflights users on 1/20. 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.
목 2/206:05 amSJU - MDW
1 stop10h 40mSouthwest
월 2/241:25 pmMDW - SJU
2 stops9h 25mSouthwest
Deal found 1/20$310
This Delta deal was found by Cheapflights users on 1/20. 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.
화 3/47:30 amSJU - MDW
1 stop10h 50mDelta
화 3/119:54 amMDW - SJU
1 stop9h 16mDelta
Deal found 1/20$325
This Booking.com deal was found by Cheapflights users on 1/20. 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.
목 2/132:20 pmSDQ - MDW
2 stops30h 00mFrontier
월 2/1712:43 pmMDW - SDQ
1 stop23h 57mFrontier
Deal found 1/20$418
This Delta deal was found by Cheapflights users on 1/21. 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.
목 2/137:05 amSDQ - MDW
2 stops13h 06mDelta
월 2/176:00 amMDW - SDQ
1 stop5h 57mDelta
Deal found 1/21$438
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
목 2/1310:00 amSDQ - MDW
1 stop10h 20mMultiple Airlines
월 2/177:25 pmMDW - SDQ
1 stop17h 05mMultiple Airlines
Deal found 1/20$445
This Delta deal was found by Cheapflights users on 1/20. 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.
화 3/48:00 amMBJ - MDW
2 stops11h 11mDelta
화 3/1112:51 pmMDW - MBJ
1 stop7h 46mDelta
Deal found 1/20$446
This Delta deal was found by Cheapflights users on 1/20. 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.
수 3/53:06 pmNAS - MDW
1 stop8h 14mDelta
수 3/129:54 amMDW - NAS
1 stop5h 06mDelta
Deal found 1/20$506
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
목 3/62:00 pmGCM - MDW
2 stops9h 06mMultiple Airlines
목 3/137:25 amMDW - GCM
1 stop13h 55mMultiple Airlines
Deal found 1/20$525
This Frontier deal was found by Cheapflights users on 1/19. 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.
토 2/1512:00 pmPUJ - MDW
1 stop12h 04mFrontier
토 2/227:10 pmMDW - PUJ
2 stops16h 04mFrontier
Deal found 1/19$529
This Southwest deal was found by Cheapflights users on 1/19. 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.
화 2/251:50 pmGCM - MDW
2 stops9h 35mSouthwest
토 3/16:30 pmMDW - GCM
2 stops17h 25mSouthwest
Deal found 1/19$556

Find flights from Caribbean Islands to Midway within your budget

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 1월 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

화 3/4

7:59 pm-3:13 pm

1 stop21h 14m

Chicago Midway

화 3/11

7:25 am-9:44 am

1 stop25h 19m

$144

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

목 2/20

6:05 am-2:45 pm

1 stop10h 40m

Chicago Midway

월 2/24

1:25 pm-12:50 am

2 stops9h 25m

$310

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

화 3/4

7:30 am-4:20 pm

1 stop10h 50m

Chicago Midway

화 3/11

12:51 pm-8:10 pm

1 stop6h 19m

$325

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

목 2/13

2:20 pm-6:20 pm

2 stops30h 00m

Chicago Midway

월 2/17

12:43 pm-2:40 pm

1 stop23h 57m

$418

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

목 2/13

7:05 am-6:11 pm

2 stops13h 06m

Chicago Midway

월 2/17

6:00 am-1:57 pm

1 stop5h 57m

$438

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

목 2/13

10:00 am-6:20 pm

1 stop10h 20m

Chicago Midway

월 2/17

7:25 pm-2:30 pm

1 stop17h 05m

$445

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

화 3/4

8:00 am-6:11 pm

2 stops11h 11m

Chicago Midway

화 3/11

12:51 pm-8:37 pm

1 stop7h 46m

$446

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

목 2/13

3:56 am-7:19 pm

1 stop17h 23m

Chicago Midway

월 2/17

12:43 pm-3:01 am

1 stop12h 18m

$455

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

수 3/5

3:06 pm-10:20 pm

1 stop8h 14m

Chicago Midway

수 3/12

9:54 am-4:00 pm

1 stop5h 06m

$506

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

목 3/6

2:00 pm-10:06 pm

2 stops9h 06m

Chicago Midway

목 3/13

7:25 am-9:20 pm

1 stop13h 55m

$525

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 53 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.

Travel insights for flights from Caribbean Islands to Midway

Get recent, data-driven insights about flights from Caribbean Islands to Midway including ideal travel times, pricing trends, and more.

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 1월 21, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 1월 21, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Chicago, such as Frontier, Southwest and Delta. 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
8.1
Very good
4,662 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Air Transat
7.8
Good
381 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

LATAM Airlines
7.5
Good
1,858 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.2
Good
2,829 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 cheapest airlines to fly from Caribbean Islands to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $70. Southwest flights start at $118 while deals on Delta start at $163 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 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 $238. On average you can expect to pay $432. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago Midway), can usually be booked for $157.

  • 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 Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 3 airlines flying from Caribbean Islands to Midway

Discover the top 3 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 1월 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$239FlexibilityNo cancel feeOn-time62%
DeltaCheapest$249Average$509FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$384FlexibilityNo cancel feeOn-time63%
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