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Midway

$87+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Nov 10 — Nov 171
1 adult
Sun 11/10
Sun 11/17
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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 November 5, 2024.

This FlightHub deal was found by Cheapflights users on 11/4. 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 12/511:45 amSJU - MDW
1 stop25h 56mFrontier
Sun 12/87:25 amMDW - SJU
1 stop16h 32mFrontier
Deal found 11/4$172
This eDestinos deal was found by Cheapflights users on 11/4. 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.
Wed 12/116:40 pmSJU - MDW
2 stops25h 32mMultiple Airlines
Sun 12/157:25 amMDW - SJU
1 stop16h 32mMultiple Airlines
Deal found 11/4$200
This Southwest deal was found by Cheapflights users on 11/5. 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 12/51:35 pmSJU - MDW
1 stop10h 05mSouthwest
Sat 1/118:35 amMDW - SJU
1 stop6h 35mSouthwest
Deal found 11/5$374
This Priceline deal was found by Cheapflights users on 11/4. 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.
Thu 12/1912:02 pmSDQ - MDW
1 stop9h 40mFrontier
Wed 1/153:12 pmMDW - SDQ
2 stops20h 14mFrontier
Deal found 11/4$377
This Delta deal was found by Cheapflights users on 11/4. 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 12/183:50 pmPUJ - MDW
1 stop8h 16mDelta
Sun 1/56:00 amMDW - PUJ
1 stop8h 34mDelta
Deal found 11/4$403
This Booking.com deal was found by Cheapflights users on 11/4. 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 12/56:37 pmPUJ - MDW
2 stops24h 35mFrontier
Sun 12/812:36 pmMDW - PUJ
1 stop20h 55mFrontier
Deal found 11/4$445
This eDestinos deal was found by Cheapflights users on 11/4. 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.
Wed 12/256:00 amSDQ - MDW
2 stops17h 17mMultiple Airlines
Sat 1/47:00 amMDW - SDQ
3 stops48h 57mMultiple Airlines
Deal found 11/4$464
This Delta deal was found by Cheapflights users on 11/4. 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 11/98:00 amSJU - MDW
1 stop11h 24mDelta
Tue 11/1210:41 amMDW - SJU
1 stop10h 41mDelta
Deal found 11/4$494
This Delta deal was found by Cheapflights users on 11/4. 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 12/41:21 pmNAS - MDW
1 stop9h 25mDelta
Wed 12/116:00 amMDW - NAS
1 stop9h 05mDelta
Deal found 11/4$504
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/82:38 pmMBJ - MDW
2 stops24h 19mMultiple Airlines
Sun 11/106:00 amMDW - MBJ
1 stop8h 52mMultiple Airlines
Deal found 11/4$559
This Southwest deal was found by Cheapflights users on 11/4. 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 11/61:45 pmMBJ - MDW
1 stop9h 40mSouthwest
Tue 11/126:10 amMDW - MBJ
2 stops7h 55mSouthwest
Deal found 11/4$598
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sat 12/2110:00 amNAS - MDW
1 stop6h 13mMultiple Airlines
Fri 12/2710:26 amMDW - NAS
1 stop9h 24mMultiple Airlines
Deal found 11/5$621

Find flights from Caribbean Islands to Midway within your budget

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 2,554,862 searches. Data last updated November 5, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 12/15

9:32 pm-1:40 pm

1 stop18h 08m

$87

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/6

3:20 am-11:29 pm

1 stop22h 09m

$120

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 1/18

2:55 pm-6:10 pm

Nonstop5h 15m

$183

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 12/18

3:50 pm-10:06 pm

1 stop8h 16m

$193

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/21

12:17 pm-7:18 pm

1 stop9h 01m

$129

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 12/25

5:10 pm-6:39 am

2 stops15h 29m

$176

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/18

2:45 pm-6:39 am

2 stops16h 54m

$200

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 1/30

11:44 am-9:29 pm

1 stop10h 45m

$182

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 2/5

3:22 pm-10:20 pm

1 stop8h 58m

$223

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 1/20

6:50 pm-12:46 pm

2 stops18h 56m

$448

Flights are sorted by cheapest first

Deals found on 11/5

Showing 1-10 of 50 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.

Travel insights for flights from Caribbean Islands to Midway

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

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

Currently, April is the cheapest month in which you can book a flight from Caribbean Islands to Chicago Midway Airport (average of $159). Flying from Caribbean Islands 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 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 November 5, 2024.

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.

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 5, 2024.
Read through reviews of airlines operating flights from Caribbean Islands to Chicago, such as Frontier, Delta and WestJet. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,082 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,830 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

LATAM Airlines
7.5
Good
1,966 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

WestJet
7.3
Good
2,800 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

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

Frontier
6.1
Okay
3,572 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.3

Comfort

8.1

Entertainment

7.7

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 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.

  • Can I find flights from Caribbean Islands to Chicago Midway Airport for under $200 on Cheapflights?

    Yes, there are multiple flights from Caribbean Islands to Chicago Midway Airport for under $200. The cheapest flight booked recently is on Frontier for just $132, but on average you can expect to pay $602.

  • Are there last-minute flights available from Caribbean Islands to Chicago Midway Airport for under $300?

    There are currently 4+ open flights from Caribbean Islands to Chicago Midway Airport within the next 7 days for less than $300.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $87. Southwest flights start at $183 while deals on Delta start at $193 one-way.

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

  • What does SJU to MDW mean?

    San Juan Luis Munoz Marin Intl Airport is SJU and Chicago Midway Airport is MDW. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Nassau Intl Airport (NAS) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Caribbean Islands to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Caribbean Islands to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Caribbean Islands to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Caribbean Islands to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Caribbean Islands to Midway that allow pets onboard?

    Many airlines flying from Caribbean Islands to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Caribbean Islands to Midway?

    Yes, you can often find last-minute deals on Caribbean Islands to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Caribbean Islands to Chicago Midway Airport flight deals updated?

    The Caribbean Islands to Chicago Midway Airport flight deals you see on this page were last updated on 11/5.

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

    Currently, April is the cheapest month in which you can book a flight from Caribbean Islands to Chicago Midway Airport (average of $159). Flying from Caribbean Islands 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 Islands to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Caribbean Islands to Midway

Discover the top 2 airlines 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 2,554,862 searches. Data last updated November 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$249Average$562FlexibilityNo cancel feeOn-timeN/A
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