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Midway

$87+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Caribbean to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean (0CB) to Midway (MDW). 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 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 November 21, 2024.

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/61:55 pmSJU - MDW
1 stop12h 25mFrontier
Mon 12/97:25 amMDW - SJU
1 stop16h 32mFrontier
Deal found 11/20$158
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.
Fri 12/65:25 amSJU - MDW
2 stops17h 37mMultiple Airlines
Mon 12/98:15 amMDW - SJU
2 stops31h 28mMultiple Airlines
Deal found 11/20$238
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.
Thu 12/126:10 amSJU - MDW
1 stop10h 05mSouthwest
Mon 12/1611:55 amMDW - SJU
2 stops10h 50mSouthwest
Deal found 11/20$312
This eDestinos deal was found by Cheapflights users on 11/19. 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 12/223:43 amBQN - MDW
2 stops37h 28mFrontier
Thu 1/234:08 pmMDW - BQN
2 stops32h 38mFrontier
Deal found 11/19$323
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Sun 12/2212:02 pmSDQ - MDW
1 stop9h 40mFrontier
Tue 12/316:49 pmMDW - SDQ
1 stop16h 16mFrontier
Deal found 11/19$356
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/126:37 pmPUJ - MDW
2 stops24h 35mFrontier
Sun 12/1512:36 pmMDW - PUJ
1 stop20h 55mFrontier
Deal found 11/20$401
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 12/57:30 amSJU - MDW
1 stop10h 45mDelta
Tue 12/106:00 amMDW - SJU
1 stop9h 15mDelta
Deal found 11/20$404
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
Sun 12/2211:45 amSDQ - MDW
1 stop14h 33mMultiple Airlines
Sun 1/1910:58 amMDW - SDQ
1 stop23h 57mMultiple Airlines
Deal found 11/19$439
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.
Wed 12/41:45 pmMBJ - MDW
2 stops9h 35mSouthwest
Fri 12/68:35 pmMDW - MBJ
2 stops16h 30mSouthwest
Deal found 11/20$549
This Delta deal was found by Cheapflights users on 11/19. 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.
Sat 12/213:54 pmSDQ - MDW
1 stop8h 12mDelta
Sun 1/199:34 amMDW - SDQ
2 stops13h 22mDelta
Deal found 11/19$606
This Delta deal was found by Cheapflights users on 11/19. 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 12/192:51 pmNAS - MDW
1 stop8h 15mDelta
Wed 12/256:00 amMDW - NAS
1 stop5h 09mDelta
Deal found 11/19$624
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.
Fri 12/63:50 pmPUJ - MDW
1 stop8h 16mDelta
Mon 12/96:00 amMDW - PUJ
1 stop8h 24mDelta
Deal found 11/20$626

Find flights from Caribbean to Midway within your budget

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/6

1:55 pm-12:20 am

1 stop12h 25m

Chicago Midway

Mon 12/9

7:25 am-1:57 am

1 stop16h 32m

$158

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/23

4:50 pm-6:01 pm

1 stop27h 11m

Chicago Midway

Mon 1/27

6:15 am-3:19 pm

2 stops31h 04m

$200

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/12

6:10 am-2:15 pm

1 stop10h 05m

Chicago Midway

Mon 12/16

11:55 am-12:45 am

2 stops10h 50m

$312

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sun 12/22

3:43 am-3:11 pm

2 stops37h 28m

Chicago Midway

Thu 1/23

4:08 pm-2:46 am

2 stops32h 38m

$323

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/23

12:50 pm-10:20 pm

1 stop11h 30m

Chicago Midway

Mon 1/27

10:57 am-11:45 pm

1 stop10h 48m

$324

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sun 12/22

12:02 pm-7:42 pm

1 stop9h 40m

Chicago Midway

Tue 12/31

6:49 pm-1:05 pm

1 stop16h 16m

$356

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 12/12

6:37 pm-5:12 pm

2 stops24h 35m

Chicago Midway

Sun 12/15

12:36 pm-11:31 am

1 stop20h 55m

$401

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sun 12/22

11:45 am-12:18 am

1 stop14h 33m

Chicago Midway

Sun 1/19

10:58 am-12:55 pm

1 stop23h 57m

$439

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Wed 2/5

3:06 pm-10:20 pm

1 stop8h 14m

Chicago Midway

Sun 2/9

6:00 am-4:01 pm

1 stop9h 01m

$474

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 1/25

4:50 pm-10:20 pm

1 stop7h 30m

Chicago Midway

Tue 1/28

6:00 am-2:22 pm

1 stop6h 22m

$497

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 54 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.

Travel insights for flights from Caribbean to Midway

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

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 $159). Flying from Caribbean to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 November 21, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean to Chicago Midway Airport as you normally would.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 November 21, 2024.
Southwest
8.1
Very good
5,015 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

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

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,015 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

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

LATAM Airlines
7.5
Good
1,939 reviews
Southwest
8.1
Very good
5,015 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

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

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
5,015 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Boarding

8.2

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 Caribbean to Midway. 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 Caribbean to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Caribbean to Chicago Midway Airport are Frontier ($87), Southwest ($105), and Delta ($162).

  • 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 San Juan Luis Munoz Marin Intl - Chicago Midway, Santo Domingo Las Americas - Chicago Midway or Nassau Intl - Chicago Midway as they are the most popular.

  • 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 $159). Flying from Caribbean to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 Caribbean to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Newark to Midway flights
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Reagan-National to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
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John F Kennedy Intl to Midway flights
Baltimore to O'Hare Intl flights
Atlanta to Midway flights
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Baltimore to Midway flights
Hobby to Midway flights
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LaGuardia to Midway flights
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Love Field to O'Hare Intl flights
Reagan-National to Midway flights
Nashville to O'Hare Intl flights
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Boston to Midway flights

Top 3 airlines flying from Caribbean to Midway

Discover the top 3 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$253FlexibilityNo cancel feeOn-time62%
DeltaCheapest$249Average$479FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$384FlexibilityNo cancel feeOn-time63%
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