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$90+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
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 January 30, 2025.

Round-trip from

$136
(Mytrip)

One-way from

$90
(Priceline)

Popular in

December

Cheapest in

January

Average price

$232

Good one-way deal

$282 or less
From Caribbean to Chicago Midway
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One-way flight from Caribbean to Chicago Midway
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in January 2025
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Price to beat on a 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 January 30, 2025.

This Mytrip deal was found by Cheapflights users on 1/29. 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.
Thu 3/66:45 amSJU - MDW
1 stop14h 50mFrontier
Mon 3/1012:26 pmMDW - SJU
1 stop11h 44mFrontier
Deal found 1/29$136
This Delta deal was found by Cheapflights users on 1/29. 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 2/67:30 amSJU - MDW
1 stop10h 50mDelta
Sun 2/96:00 amMDW - SJU
1 stop6h 36mDelta
Deal found 1/29$235
This Trip.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/73:51 amBQN - MDW
2 stops21h 38mFrontier
Sun 2/910:58 amMDW - BQN
1 stop13h 48mFrontier
Deal found 1/28$300
This Southwest deal was found by Cheapflights users on 1/29. 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 2/206:05 amSJU - MDW
1 stop10h 40mSouthwest
Mon 2/241:20 pmMDW - SJU
2 stops9h 30mSouthwest
Deal found 1/29$355
This FlightHub deal was found by Cheapflights users on 1/29. 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.
Thu 5/81:50 pmSDQ - MDW
2 stops28h 38mFrontier
Mon 5/128:30 amMDW - SDQ
2 stops14h 25mFrontier
Deal found 1/29$400
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 2/207:45 amNAS - MDW
1 stop8h 28mMultiple Airlines
Sun 2/234:19 pmMDW - NAS
1 stop17h 41mMultiple Airlines
Deal found 1/29$414
This Delta deal was found by Cheapflights users on 1/29. 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 3/117:00 amMBJ - MDW
2 stops11h 02mDelta
Tue 3/189:25 amMDW - MBJ
2 stops11h 12mDelta
Deal found 1/29$426
This Delta deal was found by Cheapflights users on 1/29. 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 2/277:05 amSDQ - MDW
2 stops13h 06mDelta
Thu 3/69:33 amMDW - SDQ
2 stops13h 23mDelta
Deal found 1/29$438
This Delta deal was found by Cheapflights users on 1/29. 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 2/13:48 pmPUJ - MDW
1 stop8h 32mDelta
Tue 2/46:00 amMDW - PUJ
1 stop6h 23mDelta
Deal found 1/29$459
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 2/2610:00 amSDQ - MDW
1 stop7h 13mMultiple Airlines
Thu 2/2712:43 pmMDW - SDQ
2 stops22h 33mMultiple Airlines
Deal found 1/29$476
This Delta deal was found by Cheapflights users on 1/30. 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 7/304:50 pmNAS - MDW
1 stop5h 57mDelta
Tue 8/56:00 amMDW - NAS
1 stop6h 54mDelta
Deal found 1/30$486
This Kissandfly.com deal was found by Cheapflights users on 1/29. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/76:35 pmSXM - MDW
2 stops22h 38mFrontier
Sun 3/162:12 pmMDW - SXM
2 stops26h 03mFrontier
Deal found 1/29$540

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/6

6:45 am-7:35 pm

1 stop14h 50m

Chicago Midway

Mon 3/10

12:26 pm-1:10 am

1 stop11h 44m

$136

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 4/15

7:30 am-6:00 pm

1 stop11h 30m

Chicago Midway

Mon 4/21

6:00 am-4:29 pm

1 stop9h 29m

$293

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/27

6:05 am-2:05 pm

1 stop10h 00m

Chicago Midway

Sun 3/2

2:30 pm-1:00 am

2 stops8h 30m

$325

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 5/8

1:50 pm-5:28 pm

2 stops28h 38m

Chicago Midway

Mon 5/12

8:30 am-11:55 pm

2 stops14h 25m

$400

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Thu 2/20

7:45 am-3:13 pm

1 stop8h 28m

Chicago Midway

Sun 2/23

4:19 pm-11:00 am

1 stop17h 41m

$414

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 3/11

7:00 am-6:02 pm

2 stops11h 02m

Chicago Midway

Tue 3/18

9:25 am-8:37 pm

2 stops11h 12m

$426

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/27

7:05 am-6:11 pm

2 stops13h 06m

Chicago Midway

Thu 3/6

6:00 am-1:57 pm

1 stop5h 57m

$438

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Thu 2/13

3:56 am-7:19 pm

1 stop17h 23m

Chicago Midway

Mon 2/17

12:43 pm-3:01 am

1 stop12h 18m

$468

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 2/26

10:00 am-3:13 pm

1 stop7h 13m

Chicago Midway

Thu 2/27

12:43 pm-1:16 pm

2 stops22h 33m

$476

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Fri 5/9

2:38 pm-9:46 pm

1 stop8h 08m

Chicago Midway

Tue 5/13

6:00 am-3:25 pm

1 stop8h 25m

$536

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 53 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 November is currently the most expensive (average of $249). 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 January 30, 2025.

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 January 30, 2025.
Southwest
8.1
Very good
4,587 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
4,587 reviews
Southwest
8.1
Very good
4,587 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
8,456 reviews
Southwest
8.1
Very good
4,587 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

Air Transat
7.8
Good
381 reviews
Southwest
8.1
Very good
4,587 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
1,838 reviews
Southwest
8.1
Very good
4,587 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
7.2
Good
2,817 reviews
Southwest
8.1
Very good
4,587 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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 ($90), Delta ($147), and Southwest ($193).

  • 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 $388, our data indicates the cheapest price to be $238. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $136.

  • 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 November is currently the most expensive (average of $249). 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 Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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Reagan-National to Midway flights
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Philadelphia to Midway flights
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Boston to Midway flights
Denver to Midway flights
Hartford to O'Hare Intl flights
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Miami to O'Hare Intl flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Hobby 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 2,558,603 searches. Data last updated January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$264FlexibilityNo cancel feeOn-time62%
DeltaCheapest$249Average$509FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$384FlexibilityNo cancel feeOn-time63%
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