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Midway

$115+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$185
(Priceline)

One-way from

$115
(Frontier)
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 June 18, 2025.

This Priceline deal was found by Cheapflights users on 6/17. 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.
Wed 7/28:15 amSJU - MDW
1 stop12h 15mFrontier
Sat 7/129:12 pmMDW - SJU
1 stop28h 27mFrontier
Deal found 6/17$185
This FlightHub deal was found by Cheapflights users on 6/17. 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.
Fri 6/2710:56 amBQN - MDW
1 stop10h 21mFrontier
Thu 7/109:12 pmMDW - BQN
1 stop12h 09mFrontier
Deal found 6/17$316
This Southwest deal was found by Cheapflights users on 6/16. 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.
Fri 7/1111:25 amSJU - MDW
1 stop9h 20mSouthwest
Tue 7/1511:15 amMDW - SJU
1 stop9h 00mSouthwest
Deal found 6/16$327
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/102:40 pmSJU - MDW
1 stop7h 46mDelta
Sun 9/146:00 amMDW - SJU
1 stop6h 23mDelta
Deal found 6/16$341
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/101:20 pmMBJ - MDW
1 stop8h 06mDelta
Wed 9/246:00 amMDW - MBJ
1 stop6h 58mDelta
Deal found 6/16$350
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/23:35 pmAUA - MDW
1 stop8h 00mFrontier
Sat 8/96:20 amMDW - AUA
1 stop7h 09mFrontier
Deal found 6/18$365
This Booking.com deal was found by Cheapflights users on 6/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/510:06 amPUJ - MDW
1 stop11h 16mFrontier
Sat 7/129:12 pmMDW - PUJ
1 stop10h 42mFrontier
Deal found 6/18$368
This FlightHub deal was found by Cheapflights users on 6/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/253:53 pmMBJ - MDW
1 stop21h 56mFrontier
Mon 6/306:20 amMDW - MBJ
1 stop8h 23mFrontier
Deal found 6/16$371
This Delta deal was found by Cheapflights users on 6/17. 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.
Tue 8/192:40 pmPUJ - MDW
1 stop8h 09mDelta
Tue 8/266:00 amMDW - PUJ
1 stop7h 34mDelta
Deal found 6/17$375
This Booking.com deal was found by Cheapflights users on 6/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/221:49 amSDQ - MDW
1 stop22h 29mFrontier
Mon 6/306:40 pmMDW - SDQ
1 stop16h 03mFrontier
Deal found 6/16$413
This Southwest deal was found by Cheapflights users on 6/16. 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.
Wed 7/163:45 pmPUJ - MDW
Nonstop4h 50mSouthwest
Wed 7/239:55 amMDW - PUJ
Nonstop4h 30mSouthwest
Deal found 6/16$443
This Delta deal was found by Cheapflights users on 6/17. 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.
Mon 10/273:15 pmSDQ - MDW
1 stop7h 29mDelta
Thu 10/309:30 amMDW - SDQ
2 stops12h 59mDelta
Deal found 6/17$450

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 June 18, 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

Wed 7/2

8:15 am-7:30 pm

1 stop12h 15m

Chicago Midway

Sat 7/12

9:12 pm-2:39 am

1 stop28h 27m

$185

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 7/11

11:25 am-7:45 pm

1 stop9h 20m

Chicago Midway

Tue 7/15

11:15 am-9:15 pm

1 stop9h 00m

$327

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/10

2:40 pm-9:26 pm

1 stop7h 46m

Chicago Midway

Sun 9/14

6:00 am-1:23 pm

1 stop6h 23m

$341

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 9/10

1:20 pm-9:26 pm

1 stop8h 06m

Chicago Midway

Wed 9/24

6:00 am-12:58 pm

1 stop6h 58m

$350

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Thu 7/10

2:59 am-3:06 pm

1 stop13h 07m

Chicago Midway

Thu 7/24

9:12 pm-2:01 am

1 stop27h 49m

$351

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Sat 8/2

3:35 pm-10:35 pm

1 stop8h 00m

Chicago Midway

Sat 8/9

6:20 am-2:29 pm

1 stop7h 09m

$365

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 7/5

10:06 am-8:22 pm

1 stop11h 16m

Chicago Midway

Sat 7/12

9:12 pm-8:54 am

1 stop10h 42m

$368

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/19

2:40 pm-9:49 pm

1 stop8h 09m

Chicago Midway

Tue 8/26

6:00 am-2:34 pm

1 stop7h 34m

$375

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 8/16

3:45 pm-1:47 pm

1 stop22h 02m

Chicago Midway

Sun 8/24

11:03 am-7:55 am

1 stop20h 52m

$376

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sun 7/13

11:50 am-3:06 pm

1 stop28h 16m

Chicago Midway

Sat 7/19

9:12 pm-10:45 am

1 stop12h 33m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 54 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 June 18, 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 June 18, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Chicago, such as Southwest, Delta and WestJet. 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
4,280 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,876 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,301 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $115. Southwest flights start at $146 while deals on Delta start at $187 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 Punta Cana - 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 $232. On average you can expect to pay $418. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago Midway), can usually be booked for $255.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$527FlexibilityNo cancel feeOn-time63%
DeltaCheapest$332Average$332FlexibilityNo cancel feeOn-timeN/A

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