Flights from Chicago to Grand Cayman Island – Airlines & connecting routes
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MDW to GCM – All flight route options from Chicago Midway International, Illinois, USA to Grand Cayman, Cayman Islands. These flights are operated by Delta Air Lines & Southwest Airlines through 3 different flight connections. The shortest flight time is 5 hours and 33 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.
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Chicago to Grand Cayman Island flights
There are over 3 and approximately 14 flights every week. While flying to Grand Cayman Island from Chicago you will be doing a stopover in Atlanta, Orlando or any other of the 3 alternatives with flight connections.
Are there any non-stop flights from MDW to GCM?
There are no direct or non-stop flights from Chicago Midway International, MDW to Grand Cayman, GCM.
Chicago to Grand Cayman Island with Delta Air Lines
If you fly from Chicago with Delta Air Lines you will do a stopover in Atlanta, ATL before reaching Grand Cayman Island. This flight trip will take 5 hours and 33 minutes and you can fly every weekday with departures at 06:00 or 06:04. Delta Air Lines is a member of SkyTeam.
Distance & flight times: Midway International Airport to Grand Cayman
The shortest flight time between MDW and GCM is 5 hours and 33 minutes.
Via | Total flight time | Layover time | Distance |
---|---|---|---|
ATL Atlanta | 5h 33m | 1h 5m | 1608 miles (2587 km) |
MCO Orlando | 6h 23m | 2h 40m | 1631 miles (2624 km) |
BWI Baltimore | 8h 0m | 2h 30m | 2021 miles (3252 km) |


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From USA to Grand Cayman Island
Below is a list of other cities in USA with flights to Grand Cayman Island with either non-stop or connecting flights.
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DFW Dallas Direct
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ORD Chicago Direct
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ATL Atlanta Direct
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DEN Denver Direct
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JFK New York Direct
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MIA Miami Direct
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CLT Charlotte Direct
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LAX Los Angeles Direct
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IAH Houston Direct
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EWR New York Direct