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Flights from Grand Cayman Island to Chicago – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

GCM to ORD flights and routes map GCM to ORD – All flight route options from Grand Cayman, Cayman Islands to Chicago O Hare International, Illinois, USA. These routes are operated by 6 airlines. Fly non-stop with American Airlines or United Airlines, or choose from 7 different stopover flights. The shortest flight time is 4 hours and 10 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
Cayman Islands GCM Grand Cayman Grand Cayman Island, Cayman Islands
USA ORD Chicago O Hare , IL, USA
GCM
Grand Cayman
Cayman IslandsGrand Cayman Island, Cayman Islands
Chicago O Hare
USAChicago, IL, USA
ORD
2 direct routes found »
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11 routes with 1 stop found »
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Non-stop route options:

Duration

American Airlines
Non-stop with American Airlines. 0-1 flights per day.
Begins in 8/11

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4h 10m

Begins in 8/11
American Airlines
Non-stop with American Airlines.
4h 10m
0-1 flights per day.
Begins in 8/11
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United Airlines
Non-stop with United Airlines. 0-1 flights per day.
Only saturdays

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4h 14m

Only saturdays
United Airlines
Non-stop with United Airlines.
4h 14m
0-1 flights per day.
Only saturdays
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1 stop route options with the same airline:

Duration

Via Dulles IAD
1 stop with United Airlines. 0-1 flights per day.
Only saturdays

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7h 15m

Only saturdays
Via Dulles IAD
1 stop with United Airlines.
7h 15m
0-1 flights per day.
Only saturdays
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Via Charlotte CLT
1 stop with American Airlines. 1-2 flights per day.

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8h 05m

Via Charlotte CLT
1 stop with American Airlines.
8h 05m
1-2 flights per day.
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Via Miami MIA
1 stop with American Airlines. 2 flights per day.

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8h 14m

Via Miami MIA
1 stop with American Airlines.
8h 14m
2 flights per day.
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Via Houston IAH
1 stop with United Airlines. 1-2 flights per day.

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8h 34m

Via Houston IAH
1 stop with United Airlines.
8h 34m
1-2 flights per day.
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Via Atlanta ATL
1 stop with Delta Air Lines. 0-1 flights per day.

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8h 43m

Via Atlanta ATL
1 stop with Delta Air Lines.
8h 43m
0-1 flights per day.
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Via Orlando MCO
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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9h 20m

Only saturdays
Via Orlando MCO
1 stop with Southwest Airlines.
9h 20m
0-1 flights per day.
Only saturdays
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1 stop route options with codeshare or different airlines:

Duration

Via Atlanta ATL With Delta Air Lines & American Airlines 0-1 flights per day.

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7h 08m

Via Atlanta ATL
7h 08m
With Delta Air Lines & American Airlines 0-1 flights per day.
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Via Miami MIA With American Airlines & United Airlines 0-1 flights per day.
Begins in 2/11

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7h 10m

Begins in 2/11
Via Miami MIA
7h 10m
With American Airlines & United Airlines 0-1 flights per day.
Begins in 2/11
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Via Houston IAH With United Airlines & American Airlines

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7h 50m

Via Houston IAH
7h 50m
With United Airlines & American Airlines
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Via Charlotte CLT With American Airlines & United Airlines 0-1 flights per day.
Only saturdays

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8h 01m

Only saturdays
Via Charlotte CLT
8h 01m
With American Airlines & United Airlines 0-1 flights per day.
Only saturdays
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Via Tampa TPA With Cayman Airways & American Airlines 0-1 flights per day.

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8h 17m

Via Tampa TPA
8h 17m
With Cayman Airways & American Airlines 0-1 flights per day.
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Grand Cayman Island to Chicago flights

With over 107 flights every week and 9 different airlines you have a wide range of options. You can fly non-stop to Chicago (ORD) from Grand Cayman Island (GCM) with United Airlines or American Airlines but if a stopover option suits you better you can choose to fly via Atlanta, Dulles or any other of the 7 alternatives with connectiing airports.

Grand Cayman Island to Chicago with United Airlines

You can fly non-stop with United Airlines every Saturday at 13 or 14 in the afternoon. You can also take a connecting flight via Dulles or Houston. United Airlines is a Star Alliance member.

With American Airlines

You can fly non-stop every weekday with flights departing at 13:00 or 14:00. You can also take a connecting flight via Charlotte or Miami. American Airlines is a member of the air alliance OneWorld.

Note Non-stop flights with American Airlines will begin in Nov 2025.

Distance & flight times: Grand Cayman to Chicago O'Hare

The shortest flight time between GCM and ORD is 4 hours and 16 minutes.

ViaTotal flight timeLayover timeDistance
Direct4h 16m-1622 miles (2610 km)
ATL Atlanta7h 8m1h 39m1624 miles (2613 km)
IAD Dulles7h 15m1h 40m1975 miles (3178 km)
CLT Charlotte8h 5m1h 30m1708 miles (2748 km)
MIA Miami8h 14m3h 35m1661 miles (2673 km)
TPA Tampa8h 17m1h 53m1626 miles (2616 km)
IAH Houston8h 34m2h 17m2082 miles (3350 km)
MCO Orlando9h 20m3h 10m1646 miles (2648 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.GCM-ORD flight routesGrand Cayman Island to Chicago flight routes illustrated on a map.
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Grand Cayman Island - Chicago route map and flight paths
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From Grand Cayman Island to USA

Below is a list of other destinations to USA from Grand Cayman with either direct flights or 1 stop connections.

From Cayman Islands to Chicago

Below is a list of other cities in Cayman Islands with flights to Chicago with either non-stop or connecting flights.

You can fly non-stop from Grand Cayman Island (GCM) to Chicago (ORD) with United Airlines or American Airlines. The flight takes approximately 4 hours and 16 minutes. If you travel with a connecting flight instead, for example via Atlanta, the total flight time will be 7 hours and 8 minutes.

If you're interested in direct flights, United Airlines or American Airlines is available. For flights with stopovers, Delta Air Lines, American Airlines, United Airlines, Cayman Airways or Southwest Airlines is also an option.

The flight time between Grand Cayman (GCM) and Chicago O Hare International (ORD) is approximately 4 hours and 16 minutes. The distance between the two airports is 1661 miles (or 2673 kilometers).

Yes, you can fly non-stop to ORD from GCM with United Airlines or American Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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