HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$83+ Cheap flights from Caribbean 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Mar 8 — Mar 151
Sat 3/8
Sat 3/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean 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 to Midway

Keep the following information in mind while searching for Caribbean to Midway flight deals. Data was last updated March 3, 2025.

Round-trip from

$168
(Frontier)

One-way from

$83
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$348

Good round-trip deal

$568 or less

Good one-way deal

$238 or less
From Caribbean to Chicago Midway
Search Deals
One-way flight from Caribbean to Chicago Midway
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals
Price to beat on a round-trip flight from Caribbean to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Caribbean to Chicago Midway.
Search Deals

Find flight deals from Caribbean to Midway

Cheapest flights from Caribbean to Midway
Explore the most affordable flight options available from Caribbean to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 3, 2025.

This Frontier deal was found by Cheapflights users on 3/2. 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 4/29:35 pmSJU - MDW
1 stop12h 49mFrontier
Wed 4/912:46 pmMDW - SJU
1 stop7h 52mFrontier
Deal found 3/2$168
This Delta deal was found by Cheapflights users on 3/1. 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 3/116:15 amSJU - MDW
1 stop6h 51mDelta
Tue 3/2512:51 pmMDW - SJU
1 stop6h 19mDelta
Deal found 3/1$296
This Southwest deal was found by Cheapflights users on 3/2. 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 5/12:00 pmSJU - MDW
1 stop10h 05mSouthwest
Wed 5/2810:05 amMDW - SJU
2 stops10h 45mSouthwest
Deal found 3/2$391
This Trip.com deal was found by Cheapflights users on 3/2. 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.
Wed 4/232:47 amBQN - MDW
1 stop10h 44mFrontier
Mon 5/121:19 pmMDW - BQN
1 stop11h 38mFrontier
Deal found 3/2$427
This Delta deal was found by Cheapflights users on 3/3. 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 3/62:00 pmPUJ - MDW
1 stop10h 20mDelta
Wed 3/126:00 amMDW - PUJ
1 stop7h 32mDelta
Deal found 3/3$447
This Delta deal was found by Cheapflights users on 3/3. 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 3/67:05 amSDQ - MDW
2 stops13h 06mDelta
Wed 3/129:54 amMDW - SDQ
2 stops14h 00mDelta
Deal found 3/3$450
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Wed 4/1612:39 pmPUJ - MDW
1 stop7h 56mMultiple Airlines
Mon 4/216:44 pmMDW - PUJ
2 stops18h 58mMultiple Airlines
Deal found 3/1$483
This Delta deal was found by Cheapflights users on 3/3. 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 5/91:11 pmNAS - MDW
1 stop5h 31mDelta
Tue 5/1310:25 amMDW - NAS
1 stop4h 39mDelta
Deal found 3/3$488
This Frontier deal was found by Cheapflights users on 3/2. 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 3/2$495
This Southwest deal was found by Cheapflights users on 3/2. 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 3/61:30 pmMBJ - MDW
Nonstop4h 15mSouthwest
Sat 3/86:20 amMDW - MBJ
1 stop6h 00mSouthwest
Deal found 3/2$499
This Booking.com deal was found by Cheapflights users on 3/1. 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.
Tue 4/152:54 pmSDQ - MDW
1 stop29h 41mFrontier
Sun 4/208:00 amMDW - SDQ
1 stop25h 42mFrontier
Deal found 3/1$522
This Southwest deal was found by Cheapflights users on 3/2. 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 5/12:30 pmPUJ - MDW
1 stop9h 10mSouthwest
Mon 5/55:45 amMDW - PUJ
1 stop8h 00mSouthwest
Deal found 3/2$535

Find flights from Caribbean to Midway within your budget

Customize your flight search to find flights from Caribbean 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 March 3, 2025.

Fly from

Caribbean

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/2

9:35 pm-9:24 am

1 stop12h 49m

Chicago Midway

Wed 4/9

12:46 pm-9:38 pm

1 stop7h 52m

$168

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/1

7:15 am-5:59 pm

1 stop11h 44m

Chicago Midway

Tue 5/6

6:04 am-4:01 pm

1 stop8h 57m

$296

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/1

2:00 pm-11:05 pm

1 stop10h 05m

Chicago Midway

Wed 5/28

10:05 am-9:50 pm

2 stops10h 45m

$391

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Wed 4/23

2:47 am-12:31 pm

1 stop10h 44m

Chicago Midway

Mon 5/12

1:19 pm-1:57 am

1 stop11h 38m

$427

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 5/1

2:41 pm-10:22 pm

1 stop8h 41m

Chicago Midway

Wed 5/7

6:00 am-1:16 pm

1 stop6h 16m

$450

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 4/15

3:55 pm-10:22 pm

1 stop7h 27m

Chicago Midway

Sun 4/20

6:04 am-2:40 pm

1 stop7h 36m

$471

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 4/16

12:39 pm-7:35 pm

1 stop7h 56m

Chicago Midway

Mon 4/21

6:44 pm-2:42 pm

2 stops18h 58m

$483

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Fri 5/9

1:11 pm-5:42 pm

1 stop5h 31m

Chicago Midway

Tue 5/13

10:25 am-4:04 pm

1 stop4h 39m

$488

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

$495

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 4/15

2:54 pm-7:35 pm

1 stop29h 41m

Chicago Midway

Sun 4/20

8:00 am-10:42 am

1 stop25h 42m

$522

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Showing 1-10 of 54 results
1
2
3
...
6

Best time to book a flight from Caribbean to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Caribbean 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 to Midway

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

What is the cheapest month to book a flight from Caribbean to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Caribbean to Chicago Midway Airport (average of $160). Flying from Caribbean 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 CB to MDW?

Find hourly flight availability from Caribbean 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 March 3, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean to Chicago Midway Airport as you normally would.

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 March 3, 2025.
Southwest
8.1
Very good
4,333 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very good
4,333 reviews
Southwest
8.1
Very good
4,333 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very good
8,068 reviews
Southwest
8.1
Very good
4,333 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Air Transat
7.8
Good
382 reviews
Southwest
8.1
Very good
4,333 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

LATAM Airlines
7.5
Good
1,763 reviews
Southwest
8.1
Very good
4,333 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Avelo Airlines
7.5
Good
Southwest
8.1
Very good
4,333 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Caribbean 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 to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Caribbean to Chicago Midway Airport are Frontier ($83), Delta ($136), and Southwest ($201).

  • What are the most popular routes from Caribbean to Chicago Midway Airport?

    When deciding which route to take from Caribbean to Chicago Midway Airport consider San Juan Luis Munoz Marin Intl - Chicago Midway, Punta Cana - Chicago Midway or Santo Domingo Las Americas - Chicago Midway as they are the most popular.

  • What are the cheapest flights from Caribbean to Chicago Midway Airport?

    Looking for the cheapest flight from Caribbean to Chicago Midway Airport? While on average our users pay $462, our data indicates the cheapest price to be $212. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $198.

  • Can I find deals for flights from Caribbean to Midway that include hotel bookings?

    Yes. In addition to deals on Caribbean to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Midway.

  • Can I find deals for business class flights from Caribbean to Midway?

    Yes. Cheapflights offers flight deals from Caribbean 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 to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Caribbean to Chicago Midway Airport (average of $160). Flying from Caribbean 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?

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

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 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
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Boston to O'Hare Intl flights
Seattle to O'Hare Intl flights
Newark to Midway flights
Dulles Intl to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Raleigh to O'Hare Intl flights
San Francisco to Midway flights
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Ontario to O'Hare Intl flights
Dulles Intl to Midway flights
Austin to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Seattle to Midway flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Baltimore to Midway flights
Love Field to O'Hare Intl flights
Burbank to O'Hare Intl flights
Tampa to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
Hobby to O'Hare Intl flights
Minneapolis to Midway flights
Mexico City to O'Hare Intl flights
Philadelphia to Midway flights
Miami to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hartford to O'Hare Intl flights
Portland to O'Hare Intl flights
Reagan-National to Midway flights
Hobby to Midway flights
San Jose to O'Hare Intl flights
Boston to Midway flights

Top 2 airlines flying from Caribbean to Midway

Discover the top 2 airlines that operate flights from Caribbean 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 March 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$278FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$419FlexibilityNo cancel feeOn-time63%
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.