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$311+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MDW
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Round-trip from

$648
(Southwest)

One-way from

$311
(Trip.com)
From Grand Cayman to Chicago Midway
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One-way flight from Grand Cayman to Chicago Midway
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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 September 29, 2025.

This Southwest deal was found by Cheapflights users on 9/28. 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 12/31:30 pmGCM - MDW
1 stop7h 05mSouthwest
Sat 12/209:40 pmMDW - GCM
2 stops13h 55mSouthwest
Deal found 9/28$648
This Southwest deal was found by Cheapflights users on 9/28. 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.
Mon 12/11:30 pmGCM - MDW
1 stop8h 05mSouthwest
Sat 12/209:40 pmMDW - GCM
2 stops13h 55mSouthwest
Deal found 9/28$790
This Southwest deal was found by Cheapflights users on 9/28. 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 11/292:20 pmGCM - MDW
2 stops8h 15mSouthwest
Sun 12/217:05 pmMDW - GCM
2 stops16h 30mSouthwest
Deal found 9/28$1,800
This Southwest deal was found by Cheapflights users on 9/28. 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 11/292:20 pmGCM - MDW
2 stops8h 15mSouthwest
Sat 12/207:00 pmMDW - GCM
2 stops16h 35mSouthwest
Deal found 9/28$1,950

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 September 29, 2025.
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

Wed 12/3

1:30 pm-5:05 am

2 stops16h 35m

Chicago Midway

Sat 12/20

9:40 pm-12:35 pm

2 stops13h 55m

$648

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 12/1

1:30 pm-8:35 pm

1 stop8h 05m

Chicago Midway

Sat 12/20

5:40 am-3:10 pm

1 stop8h 30m

$806

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 11/30

1:30 pm-11:35 pm

2 stops11h 05m

Chicago Midway

Sun 12/21

9:40 pm-12:35 pm

2 stops13h 55m

$1,800

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 11/29

2:20 pm-9:00 pm

1 stop7h 40m

Chicago Midway

Sun 12/21

5:45 pm-12:35 pm

2 stops17h 50m

$1,800

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 11/29

2:20 pm-9:35 pm

2 stops8h 15m

Chicago Midway

Sat 12/20

7:00 pm-12:35 pm

2 stops16h 35m

$1,950

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 10/13

4:45 pm-7:16 pm

3 stops50h 31m

$623

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 1/4

3:42 pm-10:16 pm

1 stop7h 34m

$1,193

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

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
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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 16h 35m. Grand Cayman and Chicago Midway Airport are separated by a distance of 1598 mi.

  • 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.

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

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