HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$110+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean Islands to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 10, 2025.

Round-trip from

$186
(Kiwi.com)

One-way from

$110
(Kiwi.com)
From Caribbean Islands to Chicago Midway
Search Deals
One-way flight from Caribbean Islands to Chicago Midway
Search Deals

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 November 10, 2025.

This eDestinos deal was found by Cheapflights users on 11/9. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:54 amSJU - MDW
1 stop12h 43mFrontier
Sat 1/32:24 pmMDW - SJU
1 stop10h 15mFrontier
Deal found 11/9$217
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:54 amSJU - MDW
1 stop31h 25mFrontier
Wed 1/73:52 pmMDW - SJU
1 stop7h 50mFrontier
Deal found 11/9$237
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:08 pmBQN - MDW
1 stop30h 59mFrontier
Thu 11/275:30 pmMDW - BQN
1 stop7h 33mFrontier
Deal found 11/9$239
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:37 pmSJU - MDW
1 stop8h 54mFrontier
Mon 11/2412:25 pmMDW - SJU
1 stop25h 50mFrontier
Deal found 11/9$241
This eDestinos deal was found by Cheapflights users on 11/9. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/232:25 amSJU - MDW
1 stop17h 41mFrontier
Wed 11/265:57 pmMDW - SJU
1 stop13h 43mFrontier
Deal found 11/9$244
This Priceline deal was found by Cheapflights users on 11/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/124:31 pmSJU - MDW
1 stop7h 41mFrontier
Sun 12/142:59 pmMDW - SJU
1 stop6h 51mFrontier
Deal found 11/10$246
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/223:55 amBQN - MDW
1 stop14h 35mFrontier
Thu 11/275:30 pmMDW - BQN
1 stop7h 33mFrontier
Deal found 11/9$247
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:37 pmSJU - MDW
1 stop8h 54mFrontier
Wed 11/265:57 pmMDW - SJU
1 stop13h 43mFrontier
Deal found 11/9$248
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/233:55 amBQN - MDW
1 stop14h 57mFrontier
Thu 11/275:30 pmMDW - BQN
1 stop7h 33mFrontier
Deal found 11/9$250
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:10 amSJU - MDW
1 stop12h 05mFrontier
Wed 11/265:57 pmMDW - SJU
1 stop13h 43mFrontier
Deal found 11/9$254
This CheapOair deal was found by Cheapflights users on 11/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:55 amSJU - MDW
1 stop20h 44mFrontier
Mon 12/83:10 pmMDW - SJU
1 stop9h 40mFrontier
Deal found 11/9$261
This Southwest deal was found by Cheapflights users on 11/9. 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.
Fri 12/511:20 amSJU - MDW
2 stops10h 15mSouthwest
Sun 12/72:20 pmMDW - SJU
1 stop9h 05mSouthwest
Deal found 11/9$265

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 November 10, 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

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Fri 11/21

12:08 pm-5:07 pm

1 stop30h 59m

Chicago Midway

Thu 11/27

5:30 pm-3:03 am

1 stop7h 33m

$239

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sat 11/22

3:55 am-4:30 pm

1 stop14h 35m

Chicago Midway

Thu 11/27

5:30 pm-3:03 am

1 stop7h 33m

$247

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 11/21

12:37 pm-7:31 pm

1 stop8h 54m

Chicago Midway

Wed 11/26

5:57 pm-9:40 am

1 stop13h 43m

$248

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sat 11/22

3:55 am-4:30 pm

1 stop14h 35m

Chicago Midway

Fri 11/28

4:46 pm-3:03 am

1 stop8h 17m

$267

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sun 11/23

3:55 am-4:52 pm

1 stop14h 57m

Chicago Midway

Fri 11/28

4:46 pm-3:03 am

1 stop8h 17m

$270

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Fri 11/21

3:55 am-5:07 pm

1 stop15h 12m

Chicago Midway

Fri 11/28

4:46 pm-3:03 am

1 stop8h 17m

$278

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sun 11/23

3:55 am-4:52 pm

1 stop14h 57m

Chicago Midway

Thu 11/27

6:05 am-3:03 am

2 stops18h 58m

$280

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 11/25

9:30 pm-4:57 pm

1 stop21h 27m

Chicago Midway

Fri 11/28

6:05 am-1:12 am

1 stop17h 07m

$280

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sat 11/22

3:55 am-4:30 pm

1 stop14h 35m

Chicago Midway

Tue 11/25

12:25 pm-3:10 am

2 stops12h 45m

$293

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

4:31 pm-10:12 pm

1 stop7h 41m

Chicago Midway

Sat 12/6

6:00 am-2:58 pm

1 stop6h 58m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/8

Showing 1-10 of 60 results
1
2
3
...
6

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, December is the cheapest month in which you can book a flight from Caribbean Islands to Chicago Midway Airport (average of $153). Flying from Caribbean Islands to Chicago Midway Airport in March is currently the most expensive (average of $427). 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 November 10, 2025.

A simple way to save on the total cost of your ticket is to fly from Caribbean Islands to Chicago Midway Airport in the morning. If you’re flexible enough to do this you can expect to save up to 42% on your trip compared to booking a flight in the afternoon.

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 November 10, 2025.
Read reviews from past customers who have flown Southwest and Delta 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
4,235 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,006 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Caribbean Islands to Chicago Midway Airport?

    There are many flights that can get you from Caribbean Islands to Chicago Midway Airport in 8h 35m. Fly via Frontier, Delta, or Southwest to get the fastest option. Airlines will cover a distance of 1967 mi. This flight may include one or multiple stops.

  • 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 Delta, which is currently one of the cheapest options available, starting at $113. Southwest flights start at $113 while deals on Frontier start at $177 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 Punta Cana - Chicago Midway, San Juan Luis Munoz Marin Intl - Chicago Midway or Santo Domingo Las Americas - Chicago Midway as they are the most popular.

  • 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, December is the cheapest month in which you can book a flight from Caribbean Islands to Chicago Midway Airport (average of $153). Flying from Caribbean Islands to Chicago Midway Airport in March is currently the most expensive (average of $427). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean Islands to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Boston to O'Hare Intl flights
Seattle to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Baltimore to Midway flights
Ontario to O'Hare Intl flights
Atlanta to Midway flights
Hobby to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Minneapolis to Midway flights
Fort Lauderdale to O'Hare Intl flights
Dulles Intl to Midway flights
LaGuardia to Midway flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Tampa to O'Hare Intl flights
Hobby to Midway flights
Orlando to O'Hare Intl flights
Los Angeles to Midway flights
Austin to O'Hare Intl flights
Seattle to Midway flights
Denver to Midway flights
Mexico City to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
George Bush Intcntl to O'Hare Intl flights
Love Field to O'Hare Intl flights
Cleveland to O'Hare Intl flights
San Diego to O'Hare Intl flights
Reagan-National to Midway flights
Hartford to O'Hare Intl flights
Detroit to O'Hare Intl flights
Portland to O'Hare Intl flights
Sacramento to O'Hare Intl flights
San Francisco to Midway flights
Philadelphia to Midway flights
Akron to O'Hare Intl flights
Boston to Midway flights

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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$265FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$392Average$551FlexibilityNo cancel feeOn-time63%
DeltaCheapest$505Average$547FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.