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Midway

$97+ Cheap flights from Caribbean Islands 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
feb. 11 — feb. 181
mié. 2/11
mié. 2/18
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Midway

Keep the following information in mind while searching for Caribbean Islands to Midway flight deals. Data was last updated enero 12, 2026.

Round-trip from

$176
(Frontier)

One-way from

$97
(Priceline)
From Caribbean Islands to Chicago Midway
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One-way flight from Caribbean Islands to Chicago Midway
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Find flight deals from Caribbean Islands to Midway

Cheapest flights from Caribbean Islands to Midway
Explore the most affordable flight options available from Caribbean Islands to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 12, 2026.

This Frontier deal was found by Cheapflights users on 1/11. 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.
mar. 3/103:22 pm
SJU
-
MDW
1 stop7h 57m
Frontier
mié. 3/256:00 am
MDW
-
SJU
1 stop7h 12m
Frontier
Deal found 1/11$176
This CheapOair deal was found by Cheapflights users on 1/11. 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.
mié. 3/113:22 pm
SJU
-
MDW
1 stop7h 57m
Frontier
mar. 3/1711:19 am
MDW
-
SJU
1 stop20h 35m
Frontier
Deal found 1/11$177
This Frontier deal was found by Cheapflights users on 1/11. 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.
jue. 2/266:00 am
SJU
-
MDW
1 stop9h 56m
Frontier
lun. 3/29:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Deal found 1/11$182
This CheapOair deal was found by Cheapflights users on 1/11. 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.
jue. 2/58:00 am
SJU
-
MDW
1 stop13h 52m
Frontier
lun. 2/97:00 pm
MDW
-
SJU
1 stop15h 57m
Frontier
Deal found 1/11$183
This Booking.com deal was found by Cheapflights users on 1/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/173:22 pm
SJU
-
MDW
1 stop7h 57m
Frontier
mié. 3/256:00 am
MDW
-
SJU
1 stop7h 12m
Frontier
Deal found 1/10$187
This Booking.com deal was found by Cheapflights users on 1/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/186:39 pm
SJU
-
MDW
1 stop20h 02m
Frontier
mié. 3/256:00 am
MDW
-
SJU
1 stop7h 12m
Frontier
Deal found 1/10$192
This Booking.com deal was found by Cheapflights users on 1/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/186:39 pm
SJU
-
MDW
1 stop20h 02m
Frontier
mar. 3/244:33 pm
MDW
-
SJU
1 stop8h 30m
Frontier
Deal found 1/10$193
This Frontier deal was found by Cheapflights users on 1/11. 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.
lun. 3/91:01 pm
SJU
-
MDW
1 stop10h 18m
Frontier
mié. 3/256:00 am
MDW
-
SJU
1 stop7h 12m
Frontier
Deal found 1/11$198
This Priceline deal was found by Cheapflights users on 1/10. 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.
mié. 2/44:36 pm
SJU
-
MDW
1 stop29h 16m
Frontier
lun. 2/91:00 pm
MDW
-
SJU
1 stop21h 57m
Frontier
Deal found 1/10$203
This Expedia deal was found by Cheapflights users on 1/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 1/294:36 pm
SJU
-
MDW
1 stop29h 16m
Frontier
dom. 2/11:00 pm
MDW
-
SJU
1 stop27h 40m
Frontier
Deal found 1/10$209
This Frontier deal was found by Cheapflights users on 1/11. 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.
jue. 3/126:30 am
SJU
-
MDW
1 stop12h 14m
Frontier
mié. 3/256:00 am
MDW
-
SJU
1 stop7h 12m
Frontier
Deal found 1/11$211
This Expedia deal was found by Cheapflights users on 1/11. 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.
jue. 3/262:42 am
BQN
-
MDW
1 stop19h 11m
Frontier
sáb. 4/43:10 pm
MDW
-
BQN
1 stop9h 48m
Frontier
Deal found 1/11$271

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands 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 enero 12, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Chicago Midway Airport that are best for you.

Fly from

Caribbean Islands

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

mar. 3/17

3:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

mié. 3/25

6:00 am-2:12 pm

1 stop7h 12m

$187

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 2/5

8:00 am-7:52 pm

1 stop13h 52m

Chicago Midway

lun. 2/9

1:00 pm-12:57 pm

1 stop21h 57m

$209

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 2/26

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

dom. 3/1

6:00 am-3:40 pm

1 stop7h 40m

$209

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 4/10

6:00 am-9:58 pm

1 stop16h 58m

Chicago Midway

lun. 4/13

6:00 am-2:01 pm

1 stop7h 01m

$210

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 2/6

8:00 am-7:52 pm

1 stop13h 52m

Chicago Midway

lun. 2/9

7:00 pm-12:57 pm

1 stop15h 57m

$210

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 3/5

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

lun. 3/9

9:51 pm-9:57 am

1 stop11h 06m

$220

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 2/19

4:11 pm-10:37 pm

1 stop8h 26m

Chicago Midway

dom. 2/22

7:30 am-9:54 am

1 stop24h 24m

$236

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 2/12

4:25 pm-2:26 pm

1 stop24h 01m

Chicago Midway

dom. 2/15

7:30 am-12:54 am

1 stop15h 24m

$254

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

sáb. 2/7

4:36 pm-7:52 pm

1 stop29h 16m

Chicago Midway

sáb. 2/14

8:00 am-1:27 pm

1 stop27h 27m

$264

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 1/23

3:55 pm-10:22 pm

1 stop8h 27m

Chicago Midway

lun. 1/26

10:46 am-11:45 pm

1 stop10h 59m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

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

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

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

Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Chicago Midway Airport (average of $204). Flying from Caribbean Islands 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 EPX to MDW?

Find hourly flight availability from Caribbean Islands 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 enero 12, 2026.

When flying from Caribbean Islands to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 enero 12, 2026.
Read reviews from past customers who have flown Southwest from Caribbean Islands to Chicago Midway Airport. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

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
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

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 Islands 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 Islands to Chicago Midway Airport?

    There are many flights that can get you from Caribbean Islands to Chicago Midway Airport in 7h 57m. Fly via Frontier or Delta to get the fastest option. Airlines will cover a distance of 2057 mi. This flight may include one or multiple stops.

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

    When deciding which route to take from Caribbean Islands 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.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Chicago Midway Airport (average of $204). Flying from Caribbean Islands 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

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Alternative routes for Caribbean Islands to Midway

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

Discover the top airline that operate flights from Caribbean Islands 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 enero 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$392Average$548FlexibilityNo cancel feeOn-time63%

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