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Caribbean Islands

$89+ Cheap flights from Midway (MDW) to Caribbean Islands

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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Midway to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

Find flight deals from Midway to Caribbean Islands

Cheapest flights from Midway to Caribbean Islands
Explore the most affordable flight options available from Midway to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Trip.com deal was found by Cheapflights users on 11/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
Fri 12/206:00 amSJU - MDW
1 stop9h 06mFrontier
Deal found 11/20$174
This eDestinos deal was found by Cheapflights users on 11/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/98:15 amMDW - SJU
2 stops31h 28mMultiple Airlines
Sat 12/143:20 amSJU - MDW
2 stops45h 25mMultiple Airlines
Deal found 11/20$254
This FlightHub deal was found by Cheapflights users on 11/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/136:48 pmMDW - PUJ
1 stop14h 43mFrontier
Fri 12/201:59 pmPUJ - MDW
1 stop11h 15mFrontier
Deal found 11/20$301
This Southwest deal was found by Cheapflights users on 11/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/712:25 pmMDW - SJU
2 stops10h 05mSouthwest
Tue 12/106:10 amSJU - MDW
2 stops10h 00mSouthwest
Deal found 11/20$312
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/116:00 amMDW - SJU
1 stop9h 15mDelta
Wed 12/183:30 pmSJU - MDW
1 stop8h 36mDelta
Deal found 11/20$354
This eDestinos deal was found by Cheapflights users on 11/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/157:15 amMDW - PUJ
3 stops52h 23mMultiple Airlines
Fri 12/204:50 pmPUJ - MDW
1 stop24h 23mMultiple Airlines
Deal found 11/20$394
This Kiwi.com deal was found by Cheapflights users on 11/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/96:17 pmMDW - MBJ
1 stop17h 50mFrontier
Sun 12/1510:04 amMBJ - MDW
1 stop7h 52mFrontier
Deal found 11/21$451
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3110:08 amMDW - MBJ
1 stop9h 43mDelta
Wed 1/224:49 pmMBJ - MDW
1 stop6h 31mDelta
Deal found 11/21$469
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/137:00 amMDW - NAS
1 stop7h 25mMultiple Airlines
Mon 12/165:30 pmNAS - MDW
2 stops20h 39mMultiple Airlines
Deal found 11/20$483
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/216:00 amMDW - PUJ
1 stop8h 40mDelta
Mon 11/253:44 pmPUJ - MDW
1 stop8h 02mDelta
Deal found 11/20$493
This Kiwi.com deal was found by Cheapflights users on 11/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/97:25 amMDW - MBJ
2 stops26h 50mMultiple Airlines
Sun 12/1510:04 amMBJ - MDW
1 stop7h 52mMultiple Airlines
Deal found 11/21$512
This FlightHub deal was found by Cheapflights users on 11/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2212:58 pmMDW - SDQ
1 stop22h 07mFrontier
Tue 12/2412:02 pmSDQ - MDW
1 stop7h 52mFrontier
Deal found 11/21$533

Find flights from Midway to Caribbean Islands within your budget

Customize your flight search to find flights from Midway to Caribbean Islands 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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 2/21

12:26 pm-1:18 am

1 stop10h 52m

San Juan Luis Munoz Marin Intl

Mon 2/24

4:00 am-7:15 pm

1 stop17h 15m

$173

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/11

7:35 am-1:57 am

2 stops40h 22m

San Juan Luis Munoz Marin Intl

Wed 1/15

8:43 pm-6:26 pm

2 stops23h 43m

$241

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/15

1:20 pm-12:40 am

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Thu 1/23

2:55 pm-7:45 pm

1 stop6h 50m

$257

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 12/13

6:48 pm-11:31 am

1 stop14h 43m

Punta Cana

Fri 12/20

1:59 pm-11:14 pm

1 stop11h 15m

$301

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 1/14

6:00 am-2:22 pm

1 stop6h 22m

Punta Cana

Tue 1/28

3:47 pm-10:20 pm

1 stop8h 33m

$353

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 12/11

6:00 am-5:15 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Wed 12/18

3:30 pm-10:06 pm

1 stop8h 36m

$354

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/5

5:52 pm-3:55 pm

2 stops20h 03m

Punta Cana

Sun 1/12

1:54 pm-3:33 pm

2 stops27h 39m

$367

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 1/7

6:00 am-2:22 pm

1 stop6h 22m

Punta Cana

Tue 1/14

4:50 pm-10:20 pm

1 stop7h 30m

$418

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 12/6

6:07 pm-1:09 pm

1 stop18h 02m

Montego Bay Sangster Intl

Thu 12/12

10:04 am-5:18 pm

1 stop8h 14m

$445

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 12/23

10:04 pm-3:08 am

2 stops51h 04m

Santo Domingo Las Americas

Sat 12/28

2:55 pm-10:33 pm

1 stop9h 38m

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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.

Travel insights for flights from Midway to Caribbean Islands

Get recent, data-driven insights about flights from Midway to Caribbean Islands including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean Islands (average of $254). Flying from Chicago Midway Airport to Caribbean Islands in March is currently the most expensive (average of $335). 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 EPX?

Find hourly flight availability from Midway to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

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 Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated November 21, 2024.
Peruse reviews from past customers who have flown with Frontier, Southwest and Delta from Chicago to Caribbean Islands to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

KLM
7.8
Good
1,349 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,536 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

Find useful and relevant information for your journey from Midway to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Caribbean Islands one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $89. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago Midway Airport to Caribbean Islands for a low price.

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

    The most popular flight routes from Chicago Midway Airport to Caribbean Islands are Chicago Midway - San Juan Luis Munoz Marin Intl, Chicago Midway - Punta Cana and Chicago Midway - Montego Bay Sangster Intl.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean Islands (average of $254). Flying from Chicago Midway Airport to Caribbean Islands in March is currently the most expensive (average of $335). 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.

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Alternative routes for Midway to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Midway to Caribbean Islands

Discover the top 4 airlines that operate flights from Midway to Caribbean Islands. 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$365FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$199Average$277FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$275Average$717FlexibilityNo cancel feeOn-time63%
DeltaCheapest$365Average$686FlexibilityNo cancel feeOn-timeN/A
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