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Midway

$102+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Frontier deal was found by Cheapflights users on 12/10. 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.
Tue 12/233:54 amSJU - MDW
1 stop12h 43mFrontier
Mon 1/58:15 amMDW - SJU
1 stop12h 00mFrontier
Deal found 12/10$243
This Frontier deal was found by Cheapflights users on 12/10. 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.
Tue 12/233:54 amSJU - MDW
1 stop12h 43mFrontier
Sat 1/32:24 pmMDW - SJU
1 stop10h 15mFrontier
Deal found 12/10$249
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/204:02 pmSJU - MDW
1 stop8h 10mFrontier
Mon 12/226:15 amMDW - SJU
1 stop24h 24mFrontier
Deal found 12/11$260
This CheapOair deal was found by Cheapflights users on 12/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:54 amSJU - MDW
1 stop12h 43mFrontier
Mon 1/56:15 amMDW - SJU
1 stop18h 24mFrontier
Deal found 12/11$268
This CheapOair deal was found by Cheapflights users on 12/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/195:09 pmSJU - MDW
1 stop29h 55mFrontier
Mon 12/226:15 amMDW - SJU
1 stop24h 24mFrontier
Deal found 12/11$286
This CheapOair deal was found by Cheapflights users on 12/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/283:55 amSJU - MDW
1 stop20h 03mFrontier
Thu 1/1511:27 amMDW - SJU
1 stop19h 58mFrontier
Deal found 12/11$294
This CheapOair deal was found by Cheapflights users on 12/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/144:31 pmSJU - MDW
1 stop7h 41mFrontier
Mon 12/153:10 pmMDW - SJU
1 stop9h 40mFrontier
Deal found 12/10$299
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/269:49 amSJU - MDW
1 stop25h 30mFrontier
Mon 12/296:15 amMDW - SJU
1 stop18h 24mFrontier
Deal found 12/11$309
This Mytrip deal was found by Cheapflights users on 12/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/124:31 pmSJU - MDW
1 stop7h 41mFrontier
Mon 12/153:10 pmMDW - SJU
1 stop9h 40mFrontier
Deal found 12/10$313
This Priceline deal was found by Cheapflights users on 12/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/213:54 amSJU - MDW
1 stop12h 11mFrontier
Mon 12/298:15 amMDW - SJU
1 stop13h 23mFrontier
Deal found 12/10$314
This Frontier deal was found by Cheapflights users on 12/10. 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.
Thu 12/253:47 pmMBJ - MDW
1 stop7h 25mFrontier
Wed 12/316:12 amMDW - MBJ
1 stop7h 17mFrontier
Deal found 12/10$322
This Frontier deal was found by Cheapflights users on 12/11. 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.
Tue 12/2312:35 pmSDQ - MDW
1 stop11h 23mFrontier
Wed 1/75:10 pmMDW - SDQ
2 stops14h 31mFrontier
Deal found 12/11$339

Find flight deals from Caribbean to Midway

Keep the following information in mind while searching for Caribbean to Midway flight deals. Data was last updated December 12, 2025.

Round-trip from

$180
(Frontier)

One-way from

$102
(Expedia)

Popular in

December

Cheapest in

February

Average price

$431

Good one-way deal

$256 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. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a one-way flight from Caribbean to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
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 December 12, 2025.
Use the filters below to find and compare flights from Caribbean to Chicago Midway Airport that are best for you.

Fly from

Caribbean

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 12/23

3:54 am-2:37 pm

1 stop12h 43m

Chicago Midway

Sat 1/3

2:24 pm-2:39 am

1 stop10h 15m

$249

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 12/30

3:54 am-2:37 pm

1 stop12h 43m

Chicago Midway

Mon 1/5

6:15 am-2:39 am

1 stop18h 24m

$268

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 1/21

7:00 pm-10:19 pm

2 stops29h 19m

Chicago Midway

Sat 1/24

9:38 am-3:12 pm

1 stop27h 34m

$275

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

6:00 am-6:54 pm

1 stop14h 54m

Chicago Midway

Mon 1/19

9:09 pm-11:33 pm

2 stops24h 24m

$276

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 12/28

3:55 am-9:58 pm

1 stop20h 03m

Chicago Midway

Thu 1/15

11:27 am-9:25 am

1 stop19h 58m

$294

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 1/21

5:40 am-1:10 pm

2 stops9h 30m

Chicago Midway

Sat 1/24

9:45 am-9:30 pm

2 stops9h 45m

$305

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 1/28

5:40 am-11:15 am

1 stop7h 35m

Chicago Midway

Wed 2/4

1:55 pm-12:35 am

2 stops8h 40m

$310

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 12/25

3:47 pm-10:12 pm

1 stop7h 25m

Chicago Midway

Wed 12/31

6:12 am-2:29 pm

1 stop7h 17m

$322

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 12/28

3:55 am-9:58 pm

1 stop20h 03m

Chicago Midway

Fri 1/2

3:10 pm-8:54 am

1 stop15h 44m

$330

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 12/23

12:35 pm-9:58 pm

1 stop11h 23m

Chicago Midway

Wed 1/7

5:10 pm-9:41 am

2 stops14h 31m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 60 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Caribbean to Chicago Midway Airport

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

Currently, December is the cheapest month in which you can book a flight from Caribbean to Chicago Midway Airport (average of $137). Flying from Caribbean to Chicago Midway Airport in March is currently the most expensive (average of $427). 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 December 12, 2025.

A simple way to save on the total cost of your ticket is to fly from Caribbean to Chicago Midway Airport in the morning. If you’re flexible enough to do this you can expect to save up to 39% on your trip compared to booking a flight in the afternoon.

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 December 12, 2025.
Read reviews from past customers who have flown Southwest and Delta from Caribbean to Chicago Midway Airport. 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
7.9
Good
4,253 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Comfort

8.0

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
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Comfort

8.0

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
8,007 reviews
Southwest
7.9
Good
4,253 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Comfort

8.0

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 Caribbean to Midway. 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 Caribbean to Chicago Midway Airport?

    Frontier, Delta, and Southwest can get you from Caribbean to Chicago Midway Airport in just under 7h 27m. Your travel time can differ by up to 5h 16m. The distance between Caribbean and Chicago Midway Airport is about 1967 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Punta Cana - Chicago Midway, San Juan Luis Munoz Marin Intl - 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 $406, our data indicates the cheapest price to be $250. The most popular route (Punta Cana - Chicago Midway), is priced around $337.

  • 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, December is the cheapest month in which you can book a flight from Caribbean to Chicago Midway Airport (average of $137). Flying from Caribbean to Chicago Midway Airport in March is currently the most expensive (average of $427). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$392Average$548FlexibilityNo cancel feeOn-time63%
DeltaCheapest$505Average$547FlexibilityNo cancel feeOn-timeN/A

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