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Midway

$83+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$143
(Flightnetwork)

One-way from

$84
(Trip.com)
From Caribbean Islands to Chicago Midway
Search Deals
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 February 20, 2025.

This Flightnetwork deal was found by Cheapflights users on 2/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:20 amSJU - MDW
1 stop12h 20mFrontier
Mon 5/51:19 pmMDW - SJU
1 stop12h 32mFrontier
Deal found 2/20$143
This Delta deal was found by Cheapflights users on 2/18. 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 3/66:15 amSJU - MDW
1 stop7h 44mDelta
Mon 3/109:54 amMDW - SJU
1 stop9h 16mDelta
Deal found 2/18$271
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/13:07 pmPUJ - MDW
1 stop9h 32mFrontier
Mon 5/56:15 amMDW - PUJ
2 stops10h 23mFrontier
Deal found 2/20$299
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/88:00 amSDQ - MDW
2 stops16h 39mFrontier
Mon 5/126:15 amMDW - SDQ
2 stops16h 40mFrontier
Deal found 2/20$352
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 5/85:35 amSJU - MDW
1 stop9h 45mSouthwest
Tue 5/136:35 amMDW - SJU
1 stop8h 00mSouthwest
Deal found 2/20$378
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/197:00 amMBJ - MDW
2 stops11h 02mDelta
Wed 3/266:00 amMDW - MBJ
1 stop9h 23mDelta
Deal found 2/19$414
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 5/22:43 pmSDQ - MDW
1 stop8h 43mDelta
Tue 5/66:04 amMDW - SDQ
2 stops11h 15mDelta
Deal found 2/20$450
This Gotogate deal was found by Cheapflights users on 2/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/232:47 amBQN - MDW
1 stop10h 44mFrontier
Sun 4/278:00 amMDW - BQN
1 stop24h 06mFrontier
Deal found 2/20$479
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 7/305:15 pmNAS - MDW
1 stop5h 32mDelta
Tue 8/56:00 amMDW - NAS
1 stop6h 54mDelta
Deal found 2/20$506
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 5/12:40 pmPUJ - MDW
1 stop8h 46mDelta
Mon 5/56:04 amMDW - PUJ
1 stop6h 11mDelta
Deal found 2/20$506
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/193:00 pmMBJ - MDW
1 stop8h 00mSouthwest
Wed 3/266:30 amMDW - MBJ
1 stop7h 30mSouthwest
Deal found 2/19$544
This Southwest deal was found by Cheapflights users on 2/20. 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.
Fri 5/92:10 pmNAS - MDW
2 stops11h 15mSouthwest
Tue 5/135:55 amMDW - NAS
1 stop6h 20mSouthwest
Deal found 2/20$597

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 February 20, 2025.

Fly from

Caribbean Islands

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/1

11:20 am-10:40 pm

1 stop12h 20m

Chicago Midway

Mon 5/5

1:19 pm-2:51 am

1 stop12h 32m

$143

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/6

6:15 am-11:59 am

1 stop7h 44m

Chicago Midway

Mon 3/10

9:54 am-8:10 pm

1 stop9h 16m

$271

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/1

3:07 pm-11:39 pm

1 stop9h 32m

Chicago Midway

Mon 5/5

6:15 am-5:38 pm

2 stops10h 23m

$299

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 5/8

8:00 am-11:39 pm

2 stops16h 39m

Chicago Midway

Mon 5/12

6:15 am-11:55 pm

2 stops16h 40m

$352

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/8

5:35 am-2:20 pm

1 stop9h 45m

Chicago Midway

Tue 5/13

6:35 am-3:35 pm

1 stop8h 00m

$378

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 3/19

7:00 am-6:02 pm

2 stops11h 02m

Chicago Midway

Wed 3/26

6:00 am-3:23 pm

1 stop9h 23m

$414

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 5/2

2:43 pm-10:26 pm

1 stop8h 43m

Chicago Midway

Tue 5/6

6:04 am-6:19 pm

2 stops11h 15m

$450

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Wed 4/23

2:47 am-12:31 pm

1 stop10h 44m

Chicago Midway

Sun 4/27

8:00 am-9:06 am

1 stop24h 06m

$479

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Wed 7/30

2:20 pm-9:47 pm

1 stop8h 27m

Chicago Midway

Tue 8/5

6:00 am-3:25 pm

1 stop8h 25m

$506

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/1

2:40 pm-10:26 pm

1 stop8h 46m

Chicago Midway

Mon 5/5

6:04 am-1:15 pm

1 stop6h 11m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 51 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 February 20, 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 February 20, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Chicago, such as Southwest, Delta and Air Transat. 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
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Air Transat
7.8
Good
380 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,801 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $84. Delta flights start at $136 while deals on Southwest start at $212 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, Nassau Intl - Chicago Midway or Santo Domingo Las Americas - 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 $212. On average you can expect to pay $338. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago Midway), can usually be booked for $199.

  • 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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Atlanta to O'Hare Intl flights
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Burbank to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Orlando to O'Hare Intl flights
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Miami to O'Hare Intl flights
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Atlanta to Midway flights
Mexico City to O'Hare Intl flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
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Denver to Midway flights
Nashville to O'Hare Intl flights

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$278FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$267Average$384FlexibilityNo cancel feeOn-time63%
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