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$109+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/274:00 pmMDW - SJU
2 stops39h 27mFrontier
Thu 12/410:42 amSJU - MDW
1 stop13h 11mFrontier
Deal found 10/28$221
This Delta deal was found by Cheapflights users on 10/27. 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.
Mon 12/86:00 amMDW - SJU
1 stop6h 14mDelta
Thu 12/117:00 amSJU - MDW
1 stop6h 55mDelta
Deal found 10/27$227
This Booking.com deal was found by Cheapflights users on 10/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/152:05 pmMDW - SJU
1 stop16h 40mFrontier
Fri 11/213:59 amSJU - MDW
1 stop15h 08mFrontier
Deal found 10/26$230
This Booking.com deal was found by Cheapflights users on 10/28. 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.
Mon 11/176:15 amMDW - SJU
1 stop7h 04mFrontier
Sat 11/223:59 amSJU - MDW
1 stop14h 31mFrontier
Deal found 10/28$240
This Frontier deal was found by Cheapflights users on 10/27. 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 12/316:12 amMDW - SJU
2 stops18h 27mFrontier
Thu 1/158:00 amSJU - MDW
1 stop8h 47mFrontier
Deal found 10/27$255
This Frontier deal was found by Cheapflights users on 10/26. 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.
Sun 11/165:40 amMDW - SJU
2 stops17h 52mFrontier
Fri 11/211:42 pmSJU - MDW
1 stop11h 47mFrontier
Deal found 10/26$258
This Booking.com deal was found by Cheapflights users on 10/27. 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.
Thu 11/206:05 amMDW - SJU
2 stops18h 49mFrontier
Tue 11/259:30 pmSJU - MDW
1 stop21h 27mFrontier
Deal found 10/27$259
This Frontier deal was found by Cheapflights users on 10/27. 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 12/88:42 pmMDW - SJU
2 stops19h 41mFrontier
Thu 12/114:31 pmSJU - MDW
1 stop7h 41mFrontier
Deal found 10/27$262
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/62:59 pmMDW - PUJ
1 stop25h 39mMultiple Airlines
Sat 12/139:38 amPUJ - MDW
1 stop14h 52mMultiple Airlines
Deal found 10/26$317
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 amMDW - PUJ
1 stop28h 54mMultiple Airlines
Wed 1/76:08 pmPUJ - MDW
2 stops31h 17mMultiple Airlines
Deal found 10/26$320
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/42:16 pmMDW - PUJ
1 stop27h 38mMultiple Airlines
Thu 12/119:38 amPUJ - MDW
1 stop14h 15mMultiple Airlines
Deal found 10/26$331
This Delta deal was found by Cheapflights users on 10/27. 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.
Sun 12/76:00 amMDW - PUJ
1 stop8h 46mDelta
Thu 12/116:11 pmPUJ - MDW
1 stop7h 36mDelta
Deal found 10/27$338

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 October 28, 2025.

Round-trip from

$209
(Booking.com)

One-way from

$109
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$360

Good round-trip deal

$686 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. 7% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago Midway to Caribbean.
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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 October 28, 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 11/17

9:20 am-11:20 pm

1 stop12h 00m

San Juan Luis Munoz Marin Intl

Fri 11/21

6:40 am-2:10 pm

2 stops9h 30m

$311

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/12

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Sat 1/17

3:00 pm-6:20 pm

Nonstop5h 20m

$332

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 12/7

6:00 am-4:46 pm

1 stop8h 46m

Punta Cana

Thu 12/11

6:11 pm-11:47 pm

1 stop7h 36m

$338

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 12/9

6:00 am-3:39 pm

1 stop7h 39m

Punta Cana

Tue 12/16

5:04 pm-11:47 pm

1 stop8h 43m

$338

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 11/17

9:27 am-1:00 pm

2 stops25h 33m

Saint Thomas Island Cyril E King

Sat 11/22

3:25 pm-4:30 pm

1 stop27h 05m

$340

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 2/2

6:00 am-2:20 pm

1 stop6h 20m

Punta Cana

Fri 2/6

3:45 pm-10:26 pm

1 stop8h 41m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 2/1

7:16 pm-4:09 pm

1 stop18h 53m

Punta Cana

Thu 2/5

4:20 pm-9:08 am

1 stop18h 48m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 11/17

6:00 am-3:38 pm

1 stop7h 38m

Punta Cana

Thu 11/20

3:50 pm-11:40 pm

1 stop9h 50m

$351

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 12/11

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Thu 12/18

1:50 pm-11:47 pm

1 stop10h 57m

$352

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 12/24

6:00 am-12:36 pm

1 stop5h 36m

George Town Owen Roberts Intl

Wed 12/31

1:52 pm-10:22 pm

1 stop9h 30m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 $133). Flying from Chicago Midway Airport to Caribbean in June 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 October 28, 2025.

It’s typically best to fly out from Chicago Midway Airport to Caribbean in the evening. Doing so could potentially save you 44% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Midway to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to Caribbean flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 28, 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
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

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

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
7,995 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
United Airlines
7.4
Good
8,996 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
Spirit Airlines
6.3
Okay
8,112 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
Frontier
5.8
Fair
3,122 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

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 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, Delta, and Frontier can get you from Chicago Midway Airport to Caribbean in just under 8h 46m. Your travel time can differ by up to 18h 22m. Airlines will cover a distance of 1967 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 Southwest, which is currently one of the cheapest options available, starting at $114. Delta flights start at $114 while deals on Frontier start at $203 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 - Punta Cana, Chicago Midway - San Juan Luis Munoz Marin Intl 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 $691, our data shows the cheapest flight currently is $666. When looking at the most popular route, (Chicago Midway - Punta Cana), you can expect to pay $317 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $133). Flying from Chicago Midway Airport to Caribbean in June 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

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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$373FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$327FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$299Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$325Average$665FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$380Average$699FlexibilityNo cancel feeOn-time63%

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