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$285+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MDW
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap 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 February 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/267:00 am
GCM
-
MDW
1 stop6h 41m
Multiple Airlines
Thu 4/25:11 pm
MDW
-
GCM
2 stops28h 24m
Multiple Airlines
Deal found 2/9$581
This Southwest deal was found by Cheapflights users on 2/10. 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.
Fri 2/131:50 pm
GCM
-
MDW
1 stop8h 10m
Southwest
Wed 2/185:00 am
MDW
-
GCM
1 stop6h 55m
Southwest
Deal found 2/10$617
This Delta deal was found by Cheapflights users on 2/9. 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 2/131:54 pm
GCM
-
MDW
1 stop9h 37m
Delta
Wed 2/186:00 am
MDW
-
GCM
1 stop5h 29m
Delta
Deal found 2/9$618
This Southwest deal was found by Cheapflights users on 2/9. 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 3/2612:40 pm
GCM
-
MDW
1 stop7h 35m
Southwest
Thu 4/26:00 am
MDW
-
GCM
1 stop5h 25m
Southwest
Deal found 2/9$883
This Delta deal was found by Cheapflights users on 2/10. 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 4/21:12 pm
GCM
-
MDW
1 stop9h 19m
Delta
Tue 4/76:00 am
MDW
-
GCM
1 stop5h 47m
Delta
Deal found 2/10$1,419

Find 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 February 12, 2026.

Round-trip from

$581
(Kiwi.com)

One-way from

$285
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$454
From Cayman Islands to Chicago Midway
Search Deals
One-way flight from Cayman Islands to Chicago Midway
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($231 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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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 February 12, 2026.
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

Thu 3/26

7:00 am-1:41 pm

1 stop6h 41m

Chicago Midway

Thu 4/2

5:11 pm-9:35 pm

2 stops28h 24m

$581

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 3/26

12:40 pm-8:15 pm

1 stop7h 35m

Chicago Midway

Thu 4/2

6:00 am-11:25 am

1 stop5h 25m

$883

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/2

1:12 pm-10:31 pm

1 stop9h 19m

Chicago Midway

Tue 4/7

6:00 am-11:47 am

1 stop5h 47m

$1,419

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 3/1

2:49 pm-10:29 pm

2 stops32h 40m

$285

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 6/6

1:45 pm-4:50 pm

1 stop27h 05m

$315

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 6/12

12:45 pm-9:20 pm

1 stop8h 35m

$328

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 6/13

1:45 pm-4:50 pm

1 stop27h 05m

$342

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 6/15

12:45 pm-9:20 pm

1 stop8h 35m

$346

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 6/6

11:30 am-7:25 pm

2 stops7h 55m

$396

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 6/19

12:45 pm-9:20 pm

1 stop8h 35m

$446

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 11 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 35m. Southwest provides one of the quickest options available for as low as $883. The distance from Cayman Islands to Chicago Midway Airport is about 1598 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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
Merrillville
Hammond
Porter
Benton Harbor

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