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Midway

$68+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
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 December 18, 2024.

Round-trip from

$158
(Booking.com)

One-way from

$68
(Trip.com)
From Caribbean to Chicago Midway
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One-way flight from Caribbean to Chicago Midway
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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 December 18, 2024.

This Trip.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/2410:28 amSJU - MDW
1 stop14h 05mFrontier
Thu 1/27:34 amMDW - SJU
1 stop14h 20mFrontier
Deal found 12/16$215
This eDestinos deal was found by Cheapflights users on 12/18. 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.
Tue 12/312:45 amSJU - MDW
1 stop20h 32mMultiple Airlines
Fri 1/32:35 pmMDW - SJU
1 stop9h 00mMultiple Airlines
Deal found 12/18$395
This FlightHub deal was found by Cheapflights users on 12/17. 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 12/271:59 pmPUJ - MDW
1 stop11h 15mFrontier
Thu 1/212:58 pmMDW - PUJ
1 stop25h 49mFrontier
Deal found 12/17$424
This Southwest deal was found by Cheapflights users on 12/16. 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.
Tue 12/246:10 amSJU - MDW
2 stops12h 55mSouthwest
Thu 1/210:15 amMDW - SJU
2 stops12h 25mSouthwest
Deal found 12/16$454
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 12/2612:02 pmSDQ - MDW
1 stop23h 29mMultiple Airlines
Wed 1/156:52 pmMDW - SDQ
2 stops20h 22mMultiple Airlines
Deal found 12/18$515
This Delta deal was found by Cheapflights users on 12/16. 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 12/273:54 pmSDQ - MDW
1 stop8h 12mDelta
Sat 1/116:00 amMDW - SDQ
1 stop5h 56mDelta
Deal found 12/16$572
This Frontier deal was found by Cheapflights users on 12/17. 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 12/256:00 amSDQ - MDW
2 stops17h 17mFrontier
Wed 1/16:25 amMDW - SDQ
2 stops15h 12mFrontier
Deal found 12/17$582
This Delta deal was found by Cheapflights users on 12/17. 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 12/287:30 amSJU - MDW
1 stop10h 47mDelta
Tue 1/76:00 amMDW - SJU
1 stop9h 14mDelta
Deal found 12/17$689
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/254:30 pmAUA - MDW
1 stop20h 00mMultiple Airlines
Mon 12/306:49 pmMDW - AUA
2 stops18h 51mMultiple Airlines
Deal found 12/17$831
This Delta deal was found by Cheapflights users on 12/17. 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 12/261:45 pmAUA - MDW
1 stop10h 21mDelta
Tue 12/316:00 amMDW - AUA
1 stop7h 20mDelta
Deal found 12/17$837
This Southwest deal was found by Cheapflights users on 12/17. 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 12/264:35 pmAUA - MDW
2 stops18h 40mSouthwest
Tue 12/316:00 amMDW - AUA
1 stop7h 30mSouthwest
Deal found 12/17$921
This Delta deal was found by Cheapflights users on 12/17. 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 12/203:47 pmGCM - MDW
1 stop7h 19mDelta
Sun 12/226:00 amMDW - GCM
1 stop7h 32mDelta
Deal found 12/17$1,019

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 2,558,603 searches. Data last updated December 18, 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 1/17

6:00 am-11:54 am

1 stop7h 54m

Chicago Midway

Mon 1/20

11:33 am-2:19 am

1 stop12h 46m

$168

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/17

10:09 pm-11:29 pm

2 stops27h 20m

Chicago Midway

Mon 1/20

7:45 am-1:59 am

1 stop16h 14m

$214

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/24

2:55 pm-7:45 pm

1 stop6h 50m

Chicago Midway

Tue 1/28

10:05 am-12:25 am

2 stops12h 20m

$279

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 1/31

2:32 pm-11:29 pm

2 stops34h 57m

Chicago Midway

Fri 2/7

6:40 am-11:10 am

1 stop26h 30m

$286

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 1/15

4:15 pm-10:20 pm

1 stop8h 05m

Chicago Midway

Wed 1/22

10:57 am-11:46 pm

1 stop10h 49m

$324

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 1/16

4:49 pm-10:20 pm

1 stop6h 31m

Chicago Midway

Sun 1/19

6:00 am-3:24 pm

1 stop8h 24m

$459

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 1/27

6:19 pm-4:16 pm

2 stops23h 57m

Chicago Midway

Mon 2/3

6:15 am-3:54 pm

2 stops31h 39m

$462

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-1:41 pm

1 stop6h 41m

$484

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 1/27

7:05 am-6:14 pm

2 stops13h 09m

Chicago Midway

Mon 2/3

6:00 am-1:57 pm

1 stop5h 57m

$519

OranjestadChicago

AUA - MDW

AUAMDW

Oranjestad Reina Beatrix

Tue 2/4

4:35 pm-10:20 pm

1 stop7h 45m

Chicago Midway

Tue 2/11

6:00 am-3:20 pm

1 stop7h 20m

$565

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 48 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, April is the cheapest month in which you can book a flight from Caribbean to Chicago Midway Airport (average of $160). Flying from Caribbean to Chicago Midway Airport in October is currently the most expensive (average of $232). 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 18, 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 December 18, 2024.
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

LATAM Airlines
7.5
Good
1,879 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.3
Good
2,818 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,479 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 ($68), Southwest ($162), and Delta ($204).

  • 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 Punta Cana - 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 $339, our data indicates the cheapest price to be $243. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $195.

  • 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, April is the cheapest month in which you can book a flight from Caribbean to Chicago Midway Airport (average of $160). Flying from Caribbean to Chicago Midway Airport in October is currently the most expensive (average of $232). 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 Caribbean to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 2,558,603 searches. Data last updated December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$260FlexibilityNo cancel feeOn-time62%
DeltaCheapest$249Average$676FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$384FlexibilityNo cancel feeOn-time63%
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