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There are 4 ways to get from Chicago to George Town 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.

Recommended option

Fly from Chicago O'Hare  •  6h 29m

  1. Fly from Chicago O'Hare (ORD) to Grand Cayman (GCM) ORD - GCM

$132 - $755

3 alternative options

Fly from Chicago Midway  •  6h 54m

  1. Fly from Chicago Midway (MDW) to Grand Cayman (GCM) MDW - GCM

$162 - $955

Train to South Bend, fly  •  10h 20m

  1. Take the train from Van Buren St. to South Bend Airport
  2. Fly from South Bend (SBN) to Grand Cayman (GCM) SBN - GCM

$203 - $1,115

Train to Milwaukee, fly  •  9h 47m

  1. Take the train from Chicago Union Station to Milwaukee Intermodal Station
  2. Fly from Milwaukee (MKE) to Grand Cayman (GCM) MKE - GCM

$210 - $1,041

Coronavirus (COVID-19) in Cayman Islands

There is widespread community transmission globally.
We have received no reports of travel restrictions in Cayman Islands. For the latest travel status, please check the official page for Cayman Islands.

For travel planning advice, please refer to our Rome2rio Coronavirus information page .

Coronavirus (COVID-19) Travel Advice

Currently, we are unable to provide international travel restriction information for Cayman Islands relating to Coronavirus (COVID-19). For the latest travel status in Cayman Islands, please check government recommendations.

Currently, we are unable to provide domestic travel restriction information for travelling within Cayman Islands. For the latest Coronavirus (COVID-19) travel status within Cayman Islands, please check government recommendations.

Currently, we are unable to provide travel restriction information for leaving United States. For the latest Coronavirus (COVID-19) travel status in United States, please check government recommendations.

Official Coronavirus (COVID-19) Information for United States

Last updated: December 2 | Data sourced from: ACAPS, OXFORD

Questions & Answers

The cheapest way to get from Chicago to George Town is to fly which costs $130 - $800 and takes 6h 29m.

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The quickest way to get from Chicago to George Town is to fly which costs $130 - $800 and takes 6h 29m.

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The distance between Chicago and George Town is 2580 km.

It takes approximately 6h 29m to get from Chicago to George Town, including transfers.

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The quickest flight from Chicago O'Hare Airport to Grand Cayman Airport is the direct flight which takes 3h 47m.

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George Town is 1h ahead of Chicago. It is currently 12:59 AM in Chicago and 1:59 AM in George Town.

Delta, JetBlue Airways, United Airlines and American Airlines offer flights from Chicago O'Hare Airport to Grand Cayman Airport.

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There are 358+ hotels available in George Town. Prices start at $100 USD per night.

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The best way to get from Chicago to Chicago O'Hare Airport is to subway which takes 42 min and costs $2 - $5.

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Map of how to get from Chicago to George Town.
Launch map view
  • Distance: 2580.3 km
  • Duration: 6h 29m

What companies run services between Chicago, IL, USA and George Town, Cayman Islands?

American Airlines, United Airlines and two other airlines fly from Chicago to George Town every 4 hours.

Airlines
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Grand Cayman
Ave. Duration
3h 47m
When
Saturday
Estimated price
$210 - $1,100
Flights from Chicago O'Hare to Grand Cayman via Miami
Ave. Duration
5h 37m
When
Every day
Estimated price
$210 - $1,100
Flights from Chicago O'Hare to Grand Cayman via Charlotte
Ave. Duration
6h 4m
When
Every day
Estimated price
$220 - $1,100
Flights from Chicago O'Hare to Grand Cayman via Dallas/Ft.Worth
Ave. Duration
6h 56m
When
Saturday and Sunday
Estimated price
$250 - $1,200
Flights from South Bend to Grand Cayman via Charlotte
Ave. Duration
5h 58m
When
Every day
Estimated price
$330 - $1,600
Flights from South Bend to Grand Cayman via Dallas/Ft.Worth
Ave. Duration
7h 56m
When
Saturday and Sunday
Estimated price
$380 - $1,900
Flights from South Bend to Grand Cayman via Chicago O'Hare
Ave. Duration
6h 17m
When
Saturday
Estimated price
$330 - $1,700
Flights from Milwaukee to Grand Cayman via Miami
Ave. Duration
5h 37m
When
Saturday
Estimated price
$290 - $1,400
Flights from Milwaukee to Grand Cayman via Charlotte
Ave. Duration
6h 8m
When
Every day
Estimated price
$290 - $1,500
Flights from Milwaukee to Grand Cayman via Dallas/Ft.Worth
Ave. Duration
6h 56m
When
Saturday and Sunday
Estimated price
$330 - $1,600
United Airlines
Website
united.com
Flights from Chicago O'Hare to Grand Cayman
Ave. Duration
3h 58m
When
Saturday
Estimated price
$260 - $850
Flights from Chicago O'Hare to Grand Cayman via Houston
Ave. Duration
6h 50m
When
Saturday and Sunday
Estimated price
$290 - $950
Flights from South Bend to Grand Cayman via Chicago O'Hare
Ave. Duration
5h 55m
When
Saturday
Estimated price
$400 - $1,400
Flights from South Bend to Grand Cayman via Chicago O'Hare, Houston
Ave. Duration
8h 59m
When
Sunday
Estimated price
$460 - $1,500
Flights from Milwaukee to Grand Cayman via Chicago O'Hare
Ave. Duration
5h 45m
When
Saturday
Estimated price
$340 - $1,200
Flights from Milwaukee to Grand Cayman via Houston
Ave. Duration
6h 49m
When
Sunday
Estimated price
$400 - $1,300
Delta
Website
delta.com
Flights from Chicago O'Hare to Grand Cayman via Atlanta
Ave. Duration
5h 50m
When
Monday to Saturday
Estimated price
$130 - $750
Flights from Chicago Midway to Grand Cayman via Atlanta
Ave. Duration
5h 43m
When
Every day
Estimated price
$160 - $950
Flights from South Bend to Grand Cayman via Atlanta
Ave. Duration
6h 50m
When
Every day
Estimated price
$190 - $1,100
Flights from Milwaukee to Grand Cayman via Atlanta
Ave. Duration
5h 50m
When
Wednesday, Thursday, Friday, Saturday and Sunday
Estimated price
$180 - $1,000
Cayman Airways
Website
caymanairways.com
Flights from Chicago Midway to Grand Cayman via Tampa
Ave. Duration
4h 25m
When
Monday, Thursday, Friday and Sunday
Estimated price
$280 - $800
Flights from Milwaukee to Grand Cayman via Tampa
Ave. Duration
5h 55m
When
Monday, Thursday, Friday and Sunday
Estimated price
$340 - $1,200
JetBlue Airways
Website
jetblue.com
Flights from Chicago O'Hare to Grand Cayman via Fort Lauderdale-Hollywood International
Ave. Duration
6h 42m
When
Thursday and Saturday
Estimated price
$250 - $1,100
Train operators
South Shore Line
Phone
+1 219-926-5744
Website
mysouthshoreline.com
Train from Van Buren St. to South Bend Airport
Ave. Duration
2h 25m
Frequency
5 times a day
Estimated price
$13 - $15
Schedules at
mysouthshoreline.com
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Chicago Union Station to Milwaukee Intermodal Station
Ave. Duration
1h 29m
Frequency
Every 4 hours
Estimated price
$27 - $40
Schedules at
amtrak.com
Coach Seat
$27 - $40
Premium
$180 - $260
Flexi Coach Seat
$40 - $60
Business Seat
$35 - $55

Want to know more about travelling around Cayman Islands

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