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$235+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MDW
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find flight deals from Cayman Islands to Midway

Cheapest flights from Cayman Islands to Midway
Explore the most affordable flight options available from Cayman Islands to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/13. 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 12/68:50 amGCM - MDW
1 stop14h 40mMultiple Airlines
Sat 12/132:59 pmMDW - GCM
1 stop19h 36mMultiple Airlines
Deal found 11/13$423
This Southwest deal was found by Cheapflights users on 11/13. 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.
Sat 12/61:55 pmGCM - MDW
1 stop7h 00mSouthwest
Sat 12/137:35 pmMDW - GCM
2 stops16h 00mSouthwest
Deal found 11/13$651

Cheap flight deals from Cayman Islands to Midway

Keep the following information in mind while searching for Cayman Islands to Midway flight deals. Data was last updated November 13, 2025.

Popular in

March

Cheapest in

January

Average price

$599
Highest demand for flights based on searches. 34% potential increase in price ($339 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 13, 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

Sat 12/6

8:50 am-10:30 pm

1 stop14h 40m

Chicago Midway

Sat 12/13

2:59 pm-11:35 am

1 stop19h 36m

$423

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 12/6

1:55 pm-7:55 pm

1 stop7h 00m

Chicago Midway

Sat 12/13

7:35 pm-12:35 pm

2 stops16h 00m

$651

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 1/31

2:34 pm-11:25 pm

2 stops9h 51m

$235

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 2/1

2:34 pm-11:25 pm

2 stops9h 51m

$235

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 2/2

12:40 pm-11:25 pm

2 stops11h 45m

$337

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 2/4

11:30 am-11:25 pm

3 stops36h 55m

$338

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 2/4

2:05 pm-10:26 pm

1 stop9h 21m

$393

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 2/3

2:05 pm-10:26 pm

1 stop9h 21m

$393

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 2/2

1:50 pm-9:00 pm

1 stop8h 10m

$396

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 1/31

3:25 pm-10:26 pm

1 stop8h 01m

$418

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 12 results
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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.

  • How long is the flight from Cayman Islands to Chicago Midway Airport?

    A quick flight from Cayman Islands to Chicago Midway Airport can take about 7h. Southwest provides one of the quickest options available for as low as $651. The distance from Cayman Islands to Chicago Midway Airport is about 1598 mi.

  • 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.

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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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