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$104+ Cheap flights from Midway (MDW) to Caribbean

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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from Midway to Caribbean

Cheapest flights from Midway to Caribbean
Explore the most affordable flight options available from Midway to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This CheapOair deal was found by Cheapflights users on 1/26. 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 4/169:14 am
MDW
-
SJU
1 stop15h 47m
Frontier
Sat 4/258:00 am
SJU
-
MDW
1 stop9h 13m
Frontier
Deal found 1/26$193
This Frontier deal was found by Cheapflights users on 1/23. 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.
Tue 2/246:10 am
MDW
-
SJU
1 stop6h 56m
Frontier
Thu 3/56:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
Deal found 1/23$197
This Travelocity deal was found by Cheapflights users on 1/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Wed 3/116:30 am
SJU
-
MDW
1 stop12h 43m
Frontier
Deal found 1/26$201
This Frontier deal was found by Cheapflights users on 1/26. 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 4/239:14 am
MDW
-
SJU
1 stop12h 34m
Frontier
Mon 4/273:18 pm
SJU
-
MDW
1 stop8h 01m
Frontier
Deal found 1/26$203
This Frontier deal was found by Cheapflights users on 1/26. 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.
Mon 2/21:00 pm
MDW
-
SJU
1 stop8h 59m
Frontier
Wed 2/115:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Deal found 1/26$206
This Frontier deal was found by Cheapflights users on 1/26. 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.
Tue 3/314:33 pm
MDW
-
SJU
1 stop8h 30m
Frontier
Wed 4/81:11 pm
SJU
-
MDW
1 stop10h 08m
Frontier
Deal found 1/26$209
This Frontier deal was found by Cheapflights users on 1/25. 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.
Mon 2/169:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Wed 2/183:53 am
SJU
-
MDW
1 stop12h 33m
Frontier
Deal found 1/25$211
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/16:15 am
MDW
-
SJU
1 stop17h 54m
Multiple Airlines
Wed 3/411:52 am
SJU
-
MDW
1 stop28h 04m
Multiple Airlines
Deal found 1/24$212
This Frontier deal was found by Cheapflights users on 1/25. 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.
Tue 2/246:10 am
MDW
-
SJU
1 stop6h 56m
Frontier
Fri 2/274:16 pm
SJU
-
MDW
1 stop8h 21m
Frontier
Deal found 1/25$213
This Priceline deal was found by Cheapflights users on 1/25. 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.
Sun 2/226:00 am
MDW
-
SJU
1 stop7h 08m
Frontier
Fri 2/273:53 am
SJU
-
MDW
1 stop13h 02m
Frontier
Deal found 1/25$217
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Tue 3/247:30 am
MDW
-
SJU
2 stops15h 28m
Multiple Airlines
Wed 3/2511:07 am
SJU
-
MDW
1 stop7h 41m
Multiple Airlines
Deal found 1/24$218
This Frontier deal was found by Cheapflights users on 1/24. 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.
Mon 3/99:51 pm
MDW
-
SJU
1 stop11h 21m
Frontier
Wed 3/116:30 am
SJU
-
MDW
1 stop12h 43m
Frontier
Deal found 1/24$220

Find flight deals from Midway to Caribbean

Keep the following information in mind while searching for Midway to Caribbean flight deals. Data was last updated January 26, 2026.

Round-trip from

$193
(CheapOair)

One-way from

$104
(Priceline)

Popular in

December

Cheapest in

April

Average price

$358

Good round-trip deal

$509 or less
From Chicago Midway to Caribbean
Search Deals
One-way flight from Chicago Midway to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Caribbean 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 January 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Caribbean that are best for you.

Fly from

Midway

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/29

8:35 am-8:55 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Sat 1/31

8:40 am-4:05 pm

1 stop9h 25m

$346

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 2/18

6:00 am-5:27 pm

1 stop9h 27m

San Juan Luis Munoz Marin Intl

Wed 2/25

3:55 pm-10:31 pm

1 stop8h 36m

$364

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 4/13

9:00 am-8:00 pm

2 stops10h 00m

San Juan Luis Munoz Marin Intl

Thu 4/16

3:45 pm-11:40 pm

1 stop8h 55m

$364

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 3/4

9:50 am-11:10 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Wed 3/11

5:15 am-12:55 pm

2 stops8h 40m

$364

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 2/25

9:50 am-8:55 pm

2 stops9h 05m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:10 am-11:35 am

1 stop7h 25m

$364

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 4/22

1:25 pm-9:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Thu 4/23

5:35 am-12:05 pm

1 stop7h 30m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/18

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Wed 2/25

4:44 pm-10:31 pm

1 stop6h 47m

$376

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 2/18

6:50 am-7:05 pm

2 stops10h 15m

San Juan Luis Munoz Marin Intl

Wed 2/25

5:40 am-1:10 pm

2 stops9h 30m

$376

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/2

1:15 pm-12:40 am

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Tue 3/3

5:40 am-1:10 pm

2 stops9h 30m

$385

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/26

10:49 am-11:58 pm

1 stop11h 09m

San Juan Luis Munoz Marin Intl

Tue 3/3

6:15 am-11:59 am

1 stop7h 44m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Caribbean

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $137). Flying from Chicago Midway Airport to Caribbean in May is currently the most expensive (average of $298). 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 MDW to CB?

Find hourly flight availability from Midway to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 26, 2026.

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

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated January 26, 2026.
Read reviews from past customers who have flown Southwest, Delta, and Spirit Airlines from Chicago Midway Airport to Caribbean. 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
4,268 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,112 reviews
Southwest
8.0
Very good
4,268 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,379 reviews
Southwest
8.0
Very good
4,268 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,058 reviews
Southwest
8.0
Very good
4,268 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Caribbean. 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 Chicago Midway Airport to Caribbean?

    Southwest and Delta can get you from Chicago Midway Airport to Caribbean in just under 9h 27m. Your travel time can differ by up to 53m. Airlines will cover a distance of 2057 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Caribbean one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $103. Delta flights start at $122 while deals on Southwest start at $126 one-way.

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

    The most popular flight routes from Chicago Midway Airport to Caribbean are Chicago Midway - San Juan Luis Munoz Marin Intl, Chicago Midway - Punta Cana and Chicago Midway - Saint Thomas Island Cyril E King.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $137). Flying from Chicago Midway Airport to Caribbean in May is currently the most expensive (average of $298). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Midway to Caribbean

Discover the top 4 airlines that operate flights from Midway to Caribbean. 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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$377FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$235FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$596FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$379Average$681FlexibilityNo cancel feeOn-time63%

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