There are 4 ways to get from Cayman Islands to Chicago by plane or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Chicago O'Hare International Airport
best- Fly from Georgetown Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD)plane GCM - ORD
7h 32m$118–520Fly to Chicago Midway International Airport
- Fly from Georgetown Owen Roberts International Airport (GCM) to Chicago Midway International Airport (MDW)plane GCM - MDW
8h 58m$167–738Fly to South Bend, train
- Fly from Georgetown Owen Roberts International Airport (GCM) to South Bend (SBN)plane GCM - SBN
- Take the train from South Bend Airport to Van Buren St.train
11h 43m$162–675Fly to General Mitchell International Airport, train
- Fly from Georgetown Owen Roberts International Airport (GCM) to General Mitchell International Airport (MKE)plane GCM - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
11h 37m$272–1,076
Georgetown Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) flights
Comparing Your Travel Options
The cheapest way to get from Cayman Islands to Chicago is to fly which costs $110 - $550 and takes 7h 32m.
The fastest way to get from Cayman Islands to Chicago is to fly which takes 7h 32m and costs $110 - $550.
The distance between Cayman Islands and Chicago is 1643 miles.
It takes approximately 7h 32m to get from Cayman Islands to Chicago, including transfers.
Chicago is 1h behind Cayman Islands. It is currently 10:14 PM in Cayman Islands and 9:14 PM in Chicago.
There are 1315+ hotels available in Chicago.
What companies run services between Cayman Islands and Chicago, IL, USA?
American Airlines, United Airlines, and Delta fly from Georgetown Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) 4 times a day.
- Website
- aa.com
Flights from Georgetown Owen Roberts International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 40m
- When
- Saturday
- Estimated price
- $110–550
Flights from Georgetown Owen Roberts International Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 7h 27m
- When
- Saturday
- Estimated price
- $120–550
Flights from Georgetown Owen Roberts International Airport to Chicago O'Hare International Airport via Miami
- Ave. Duration
- 7h 15m
- When
- Every day
- Estimated price
- $110–550
Flights from Georgetown Owen Roberts International Airport to South Bend via Charlotte
- Ave. Duration
- 10h 2m
- When
- Every day
- Estimated price
- $150–700
Flights from Georgetown Owen Roberts International Airport to General Mitchell International Airport via Charlotte
- Ave. Duration
- 7h 52m
- When
- Every day
- Estimated price
- $230–1,100
Flights from Georgetown Owen Roberts International Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 7h 12m
- When
- Saturday
- Estimated price
- $220–1,000
Flights from Georgetown Owen Roberts International Airport to General Mitchell International Airport via Miami
- Ave. Duration
- 7h 48m
- When
- Saturday
- Estimated price
- $220–1,000
- Website
- delta.com
Flights from Georgetown Owen Roberts International Airport to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 6h 25m
- When
- Every day
- Estimated price
- $110–550
Flights from Georgetown Owen Roberts International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 8h 22m
- When
- Saturday
- Estimated price
- $120–550
Flights from Georgetown Owen Roberts International Airport to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 10h 14m
- When
- Every day
- Estimated price
- $160–750
Flights from Georgetown Owen Roberts International Airport to South Bend via Detroit
- Ave. Duration
- 7h 55m
- When
- Saturday
- Estimated price
- $150–700
Flights from Georgetown Owen Roberts International Airport to South Bend via Atlanta
- Ave. Duration
- 8h 16m
- When
- Every day
- Estimated price
- $140–700
Flights from Georgetown Owen Roberts International Airport to General Mitchell International Airport via Detroit
- Ave. Duration
- 8h 20m
- When
- Saturday
- Estimated price
- $230–1,100
Flights from Georgetown Owen Roberts International Airport to General Mitchell International Airport via Atlanta
- Ave. Duration
- 8h 21m
- When
- Every day
- Estimated price
- $220–1,000
- Website
- southwest.com
Flights from Georgetown Owen Roberts International Airport to Chicago Midway International Airport via Orlando
- Ave. Duration
- 6h 25m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $160–750
Flights from Georgetown Owen Roberts International Airport to Chicago Midway International Airport via Charlotte
- Ave. Duration
- 5h 50m
- When
- Saturday
- Estimated price
- $170–750
Flights from Georgetown Owen Roberts International Airport to Chicago Midway International Airport via Tampa
- Ave. Duration
- 6h 45m
- When
- Monday, Thursday, Sunday, and Saturday
- Estimated price
- $160–750
Flights from Georgetown Owen Roberts International Airport to Chicago Midway International Airport via Miami
- Ave. Duration
- 8h 26m
- When
- Monday, Tuesday, Wednesday, Thursday, and Saturday
- Estimated price
- $160–750
Flights from Georgetown Owen Roberts International Airport to General Mitchell International Airport via Orlando
- Ave. Duration
- 6h 40m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $220–1,000
- Website
- united.com
Flights from Georgetown Owen Roberts International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 18m
- When
- Saturday
- Estimated price
- $110–550
Flights from Georgetown Owen Roberts International Airport to South Bend via Chicago O'Hare International Airport
- Ave. Duration
- 7h 45m
- When
- Saturday
- Estimated price
- $150–700
Flights from Georgetown Owen Roberts International Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 6h 55m
- When
- Saturday
- Estimated price
- $220–1,000
- Website
- flybreeze.com
Flights from Georgetown Owen Roberts International Airport to South Bend via Orlando
- Ave. Duration
- 6h 36m
- When
- Thursday and Sunday
- Estimated price
- $220–1,100
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Hourly
- Estimated price
- $14–17
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $14–17
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Every 4 hours
- Estimated price
- $4–16
- Schedules at
- Northern Indiana Commuter Transportation District
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $45–75
- Website
- Amtrak
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