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$112+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Caribbean

Keep the following information in mind while searching for Midway to Caribbean flight deals. Data was last updated September 11, 2025.

Round-trip from

$230
(Kiwi.com)

One-way from

$112
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$317

Good round-trip deal

$476 or less

Good one-way deal

$126 or less
From Chicago Midway to Caribbean
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One-way flight from Chicago Midway to Caribbean
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Highest demand for flights based on searches. 10% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Caribbean.
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Price to beat on a one-way flight from Chicago Midway to Caribbean.
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Find 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/136:30 amMDW - SJU
1 stop12h 14mMultiple Airlines
Sun 11/162:11 amSJU - MDW
1 stop14h 22mMultiple Airlines
Deal found 9/9$230
This Frontier deal was found by Cheapflights users on 9/11. 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.
Fri 10/35:15 pmMDW - SJU
2 stops15h 41mFrontier
Sat 10/412:28 amSJU - MDW
1 stop7h 43mFrontier
Deal found 9/11$235
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/912:30 pmMDW - SJU
1 stop11h 06mMultiple Airlines
Tue 10/141:59 amSJU - MDW
1 stop30h 26mMultiple Airlines
Deal found 9/9$239
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/235:56 pmMDW - SJU
1 stop31h 06mFrontier
Sun 10/262:12 amSJU - MDW
1 stop21h 51mFrontier
Deal found 9/9$240
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1710:33 amMDW - SJU
1 stop8h 23mFrontier
Fri 10/246:22 amSJU - MDW
2 stops18h 24mFrontier
Deal found 9/10$244
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:05 amMDW - SJU
2 stops17h 25mFrontier
Thu 10/169:06 pmSJU - MDW
1 stop13h 27mFrontier
Deal found 9/10$251
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Tue 10/75:56 pmMDW - SJU
1 stop20h 28mFrontier
Tue 10/146:22 amSJU - MDW
1 stop18h 03mFrontier
Deal found 9/9$253
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/28:15 amMDW - SJU
1 stop14h 08mFrontier
Sat 10/412:28 amSJU - MDW
1 stop7h 43mFrontier
Deal found 9/11$254
This Frontier deal was found by Cheapflights users on 9/11. 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.
Fri 10/36:21 amMDW - SJU
1 stop8h 01mFrontier
Tue 10/76:22 amSJU - MDW
2 stops17h 58mFrontier
Deal found 9/11$256
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:15 amMDW - SJU
1 stop7h 13mFrontier
Sat 10/256:22 amSJU - MDW
2 stops17h 25mFrontier
Deal found 9/10$259
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/196:20 amMDW - SJU
1 stop6h 49mFrontier
Fri 10/246:22 amSJU - MDW
2 stops18h 24mFrontier
Deal found 9/10$261
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Mon 10/2712:17 pmMDW - PUJ
1 stop8h 12mMultiple Airlines
Sat 11/19:38 amPUJ - MDW
1 stop12h 44mMultiple Airlines
Deal found 9/11$335

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 September 11, 2025.
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

Mon 9/22

5:15 pm-9:56 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

$280

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/18

1:45 pm-11:45 pm

2 stops9h 00m

San Juan Luis Munoz Marin Intl

Fri 10/31

5:40 am-1:00 pm

2 stops8h 20m

$331

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 10/1

6:15 am-5:25 pm

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Wed 10/8

2:45 pm-10:45 pm

1 stop9h 00m

$331

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/25

12:50 pm-11:25 pm

2 stops9h 35m

San Juan Luis Munoz Marin Intl

Fri 10/31

5:40 am-1:00 pm

2 stops8h 20m

$331

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 11/3

2:10 pm-12:35 am

2 stops8h 25m

San Juan Luis Munoz Marin Intl

Wed 11/12

6:40 am-1:45 pm

1 stop9h 05m

$347

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 11/11

6:26 pm-4:26 pm

1 stop20h 00m

Santo Domingo Las Americas

Tue 11/18

6:10 am-11:55 pm

1 stop19h 45m

$356

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 11/1

1:45 pm-11:45 pm

2 stops9h 00m

San Juan Luis Munoz Marin Intl

Fri 11/7

6:40 am-2:10 pm

2 stops9h 30m

$371

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 10/8

6:55 am-5:15 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Wed 10/15

6:10 am-2:25 pm

1 stop9h 15m

$371

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/31

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/7

4:30 pm-11:25 pm

1 stop8h 55m

$375

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 9/23

6:30 pm-12:20 pm

2 stops16h 50m

Santo Domingo Las Americas

Sat 9/27

6:03 am-9:10 pm

2 stops16h 07m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $254). Flying from Chicago Midway Airport to Caribbean in June is currently the most expensive (average of $339). 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 September 11, 2025.

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 September 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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 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, Southwest, and Delta can get you from Chicago Midway Airport to Caribbean in just under 9h. Your travel time can differ by up to 7h 50m. 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 $130. Southwest flights start at $152 while deals on Delta start at $169 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 - Montego Bay Sangster Intl.

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

    While on average a flight from Chicago Midway Airport to Caribbean is generally $573, our data shows the cheapest flight currently is $464. When looking at the most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), you can expect to pay $261 for that flight.

  • 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $254). Flying from Chicago Midway Airport to Caribbean in June is currently the most expensive (average of $339). 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

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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 5 airlines flying from Midway to Caribbean

Discover the top 5 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$133Average$372FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$365FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$633FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$360Average$680FlexibilityNo cancel feeOn-time63%

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