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Fares from $220 One Way, $575 Round Trip from Grand Cayman to Chicago

Prices starting at $575 for return flights and $220 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from Grand Cayman

Flights from Grand Cayman to Chicago - Frequently Asked Questions

Are there non-stop flights from Grand Cayman to Chicago?

United Airlines will fly you directly from George Town Airport (GCM-Owen Roberts Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.), which means you won't have to worry about switching planes or missing your connecting flight on this route.

What is the shortest flight from Grand Cayman to Chicago?

Jetting from George Town Airport (GCM-Owen Roberts Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.) takes at least 4 hours and 5 minutes. Savor a wine and read a few magazines — it's a golden opportunity to sit back and relax.

Route Information for Flights from Grand Cayman to Chicago

Origin Airport IATA CodeGCM
Destination Airport IATA CodeCHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Flights Review

Mar 9, 2018

Fabulous airline.

Find Cheap Flights from Grand Cayman to Chicago

Owen Roberts International Airport

Low-cost flights from Grand Cayman Island are within your reach when you book with Orbitz.com. The Owen Roberts International Airport is the largest airport in the Cayman Islands. It is also the base of operations for Cayman Airways. The main terminal is just a couple of miles from the capital city of George Town. Cayman Airways Express operates flights between the various islands, while Delta, United Airlines, US Airways and British Airways also handle international flights. Owen Roberts International Airport also welcomes private aircraft to use their facilities.

Parking at the Airport

Both short-term and long-term parking are available at Owen Roberts International Airport. Short-term parking costs CI$2.00 per hour, while long-term rates are CI$7.00 per day. Entry to the lots is managed by computerized access systems, as are the payment terminals.

Transportation to the Airport

Several bus companies do business on Grand Cayman Island and provide transport to the airport, including an airport bus service that runs into George Town. Taxi service is available as well, and more than a dozen rental car agencies have offices in or near the airport. If you rent a car during your visit, then it's a simple matter of dropping the vehicle off and walking into the terminal when you're ready to leave.

Restaurants at Owen Roberts International Airport

The Hungry Horse Restaurant is located on the second floor of the terminal and features an open-air patio. You can also grab a snack or a cocktail at the Runaway Bar in the departure lounge. When you plan your departure with Orbitz.com, you are sure to get the premium fares for flights from Grand Cayman Island.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.