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$340+ Cheap flights from Grand Cayman 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MDW
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from Grand Cayman to Midway

Keep the following information in mind while searching for Grand Cayman to Midway flight deals. Data was last updated January 12, 2026.

Round-trip from

$465
(Southwest)

One-way from

$340
(Kiwi.com)

Popular in

March

Cheapest in

December
From Grand Cayman to Chicago Midway
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One-way flight from Grand Cayman to Chicago Midway
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Highest demand for flights based on searches. 33% potential increase in price ($331 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($39 potential savings vs. average RT price).
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Find flight deals from Grand Cayman to Midway

Cheapest flights from Grand Cayman to Midway
Explore the most affordable flight options available from Grand Cayman to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 12, 2026.

This Southwest deal was found by Cheapflights users on 1/10. 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.
Thu 4/301:05 pm
GCM
-
MDW
1 stop10h 35m
Southwest
Sun 5/35:05 am
MDW
-
GCM
1 stop6h 50m
Southwest
Deal found 1/10$465
This Delta deal was found by Cheapflights users on 1/12. 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 2/211:54 pm
GCM
-
MDW
1 stop9h 37m
Delta
Wed 2/256:00 am
MDW
-
GCM
1 stop5h 29m
Delta
Deal found 1/12$474
This Delta deal was found by Cheapflights users on 1/11. 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 2/251:54 pm
GCM
-
MDW
1 stop9h 37m
Delta
Wed 3/46:00 am
MDW
-
GCM
1 stop5h 29m
Delta
Deal found 1/11$523
This Southwest deal was found by Cheapflights users on 1/12. 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 6/1112:45 pm
GCM
-
MDW
1 stop8h 35m
Southwest
Sun 6/148:40 pm
MDW
-
GCM
2 stops15h 10m
Southwest
Deal found 1/12$602
This Southwest deal was found by Cheapflights users on 1/12. 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 2/211:25 pm
GCM
-
MDW
2 stops20h 25m
Southwest
Wed 2/255:00 am
MDW
-
GCM
1 stop6h 55m
Southwest
Deal found 1/12$785

Cheapflights Fare Finder

 
Customize your flight search to find flights from Grand Cayman 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 12, 2026.
Use the filters below to find and compare flights from Grand Cayman to Chicago Midway Airport that are best for you.

Fly from

Grand Cayman

Fly to

Midway

Route

Depart

Return

Price

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/30

1:05 pm-11:40 pm

1 stop10h 35m

Chicago Midway

Sun 5/3

5:05 am-11:55 am

1 stop6h 50m

$465

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/21

1:54 pm-10:31 pm

1 stop9h 37m

Chicago Midway

Wed 2/25

6:00 am-12:29 pm

1 stop5h 29m

$474

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 2/25

1:54 pm-10:31 pm

1 stop9h 37m

Chicago Midway

Wed 3/4

6:00 am-12:29 pm

1 stop5h 29m

$523

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 6/11

12:45 pm-9:20 pm

1 stop8h 35m

Chicago Midway

Sun 6/14

8:40 pm-11:50 am

2 stops15h 10m

$602

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/21

1:25 pm-8:50 am

2 stops20h 25m

Chicago Midway

Wed 2/25

5:00 am-12:55 pm

1 stop6h 55m

$785

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/21

8:50 am-9:29 pm

2 stops37h 39m

$340

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/21

3:40 pm-10:31 pm

1 stop7h 51m

$419

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 1/20

2:05 pm-10:22 pm

1 stop9h 17m

$864

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Best time to book a flight from Grand Cayman to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Grand Cayman 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 Grand Cayman 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 Grand Cayman 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 Grand Cayman to Chicago Midway Airport?

    Departing from Grand Cayman to Chicago Midway Airport will take you 9h 37m. Grand Cayman and Chicago Midway Airport are separated by a distance of 1598 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Grand Cayman to Midway that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Grand Cayman 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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Alternative routes for Grand Cayman to Midway

See prices for flight routes from nearby airports that may be better suited for you.
George Town to O'Hare Intl flights

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