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$97+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 21, 2026.

This Frontier deal was found by Cheapflights users on 1/21. 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 3/54:11 pm
SJU
-
MDW
1 stop8h 18m
Frontier
Deal found 1/21$197
This Travelocity deal was found by Cheapflights users on 1/20. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:00 am
MDW
-
SJU
1 stop8h 21m
Frontier
Wed 2/1811:07 am
SJU
-
MDW
1 stop29h 19m
Frontier
Deal found 1/20$199
This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair 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
Sun 3/83:08 am
SJU
-
MDW
1 stop11h 00m
Frontier
Deal found 1/20$201
This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/21:00 pm
MDW
-
SJU
1 stop24h 26m
Frontier
Thu 2/124:11 pm
SJU
-
MDW
1 stop8h 23m
Frontier
Deal found 1/20$203
This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/126:15 am
MDW
-
SJU
1 stop18h 20m
Frontier
Thu 2/194:25 pm
SJU
-
MDW
1 stop24h 01m
Frontier
Deal found 1/20$204
This Frontier deal was found by Cheapflights users on 1/20. 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.
Tue 3/3111:19 am
MDW
-
SJU
1 stop11h 39m
Frontier
Wed 4/81:11 pm
SJU
-
MDW
1 stop10h 08m
Frontier
Deal found 1/20$209
This Priceline deal was found by Cheapflights users on 1/21. 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.
Mon 2/169:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Thu 2/194:25 pm
SJU
-
MDW
1 stop24h 01m
Frontier
Deal found 1/21$211
This Frontier deal was found by Cheapflights users on 1/20. 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.
Tue 2/246:10 am
MDW
-
SJU
1 stop6h 56m
Frontier
Fri 2/274:16 pm
SJU
-
MDW
1 stop8h 21m
Frontier
Deal found 1/20$213
This Super.com deal was found by Cheapflights users on 1/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:30 am
MDW
-
SJU
1 stop17h 23m
Frontier
Thu 2/266:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
Deal found 1/21$215
This Priceline deal was found by Cheapflights users on 1/20. 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 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 1/20$217
This Frontier deal was found by Cheapflights users on 1/21. 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 3/96:15 am
MDW
-
SJU
1 stop6h 54m
Frontier
Tue 3/106:30 am
SJU
-
MDW
1 stop12h 43m
Frontier
Deal found 1/21$220
This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 am
MDW
-
SJU
1 stop17h 23m
Frontier
Fri 3/63:58 am
SJU
-
MDW
1 stop11h 10m
Frontier
Deal found 1/20$222

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 21, 2026.

Round-trip from

$197
(Frontier)

One-way from

$97
(Priceline)

Popular in

December

Cheapest in

April

Average price

$356

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 ($46 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 21, 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 4/9

2:56 pm-12:52 am

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Mon 4/13

5:45 am-8:09 pm

1 stop15h 24m

$243

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 3/24

11:19 am-10:45 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Mon 4/6

1:11 pm-10:19 pm

1 stop10h 08m

$271

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 2/28

8:00 am-9:39 am

1 stop23h 39m

Santo Domingo Las Americas

Sat 3/7

11:56 am-11:32 pm

1 stop13h 36m

$348

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 4/20

10:49 am-8:06 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Tue 4/28

12:50 pm-10:29 pm

1 stop10h 39m

$364

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 5/13

12:50 pm-10:40 pm

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Sat 5/16

10:00 am-6:15 pm

1 stop9h 15m

$364

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 4/15

12:50 pm-10:40 pm

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Wed 4/22

2:00 pm-7:45 pm

1 stop6h 45m

$384

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 5/14

5:35 am-2:55 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Tue 5/19

5:05 am-3:50 pm

2 stops11h 45m

$388

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 4/26

8:50 pm-9:10 am

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Sun 5/3

5:20 pm-11:40 pm

1 stop7h 20m

$390

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/23

6:45 am-3:15 pm

1 stop7h 30m

Montego Bay Sangster Intl

Fri 2/27

1:30 pm-12:55 am

2 stops12h 25m

$397

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 2/21

8:00 am-9:39 am

1 stop23h 39m

Santo Domingo Las Americas

Sun 3/1

10:46 am-10:29 pm

2 stops37h 43m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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 21, 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 21, 2026.
Read reviews from past customers who have flown Southwest, Delta, and Frontier 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
4,266 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
8,087 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
3,056 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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?

    Frontier, Delta, and Southwest can get you from Chicago Midway Airport to Caribbean in just under 8h 17m. Your travel time can differ by up to 39m. 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 $65. 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 - Nassau Intl.

  • 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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Midway to Los Angeles flights
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Top 3 airlines flying from Midway to Caribbean

Discover the top 3 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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$377FlexibilityNo cancel feeOn-time62%
DeltaCheapest$196Average$581FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$381Average$670FlexibilityNo cancel feeOn-time63%

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