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$375+ Cheap flights from the Cayman 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MDW
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Find flight deals from Cayman Islands to Midway

One-way flights from Cayman Islands to Midway
Search for one-way flight options from Cayman Islands to Midway. Find affordable one-way fares based on user searches. Data last updated septiembre 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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.
vie. 12/51:30 pmGCM - MDW
1 stop7h 00mSouthwest
Deal found 9/15$375
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
vie. 12/511:25 amGCM - MDW
2 stops51h 11mMultiple Airlines
Deal found 9/15$378
This Delta deal was found by Cheapflights users on 9/14. 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.
dom. 9/2812:52 pmGCM - MDW
1 stop8h 44mDelta
Deal found 9/14$463
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/281:30 pmGCM - MDW
3 stops24h 37mMultiple Airlines
Deal found 9/16$495
This Delta deal was found by Cheapflights users on 9/15. 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.
vie. 11/281:50 pmGCM - MDW
1 stop10h 42mDelta
Deal found 9/15$523
This Southwest deal was found by Cheapflights users on 9/15. 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.
vie. 11/281:30 pmGCM - MDW
2 stops10h 30mSouthwest
Deal found 9/15$650
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
sáb. 11/297:00 amGCM - MDW
2 stops28h 05mMultiple Airlines
Deal found 9/15$692

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cayman 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 2,558,603 searches. Data last updated septiembre 16, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Chicago Midway Airport that are best for you.

Fly from

Cayman Islands

Fly to

Midway

Route

Depart

Return

Price

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 12/5

1:30 pm-7:30 pm

1 stop7h 00m

$375

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 12/5

11:25 am-1:36 pm

2 stops51h 11m

$378

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

dom. 9/28

12:52 pm-9:36 pm

1 stop8h 44m

$463

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 11/28

1:50 pm-11:32 pm

1 stop10h 42m

$523

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 11/28

1:30 pm-11:00 pm

2 stops10h 30m

$650

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

sáb. 11/29

7:00 am-10:05 am

2 stops28h 05m

$692

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 11/28

7:00 am-10:43 pm

3 stops16h 43m

$773

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Best time to book a flight from Cayman Islands to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Cayman 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.

Cheapflights Insights

Everything you need to know about your flight from the Cayman Islands to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Cayman 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 deals for flights from Cayman Islands to Midway that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Cayman 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.

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

    Currently, April is the cheapest month in which you can book a flight from Cayman Islands to Chicago Midway Airport (average of $160). Flying from Cayman Islands 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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