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Fares from $161 One Way, $402 Round Trip from Chicago to Grand Cayman

Prices starting at $402 for return flights and $161 for one-way flights to Grand Cayman were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

More About Flying To Grand Cayman from Chicago

Flights from Chicago to Grand Cayman - Frequently Asked Questions

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

Yes, you'll be happy to hear that you can jet straight from Chicago, IL (ORD-O'Hare Intl.) to George Town (GCM-Owen Roberts Intl.). Nonstop flights can be booked with United Airlines and American Airlines.

What is the shortest flight from Chicago to Grand Cayman?

Traveling from Chicago, IL (ORD-O'Hare Intl.) to George Town (GCM-Owen Roberts Intl.) will take a minimum of 3 hours and 15 minutes. Enjoy a wine and watch a movie or two — here's your chance to just relax.

What airlines have the most flights from Chicago to Grand Cayman?

Consider booking a ticket with United Airlines (UA), which frequently services this route. This airline operates 5 flights every month between Chicago, IL (ORD-O'Hare Intl.) and George Town (GCM-Owen Roberts Intl.). Also explore the deals available with American Airlines (AA). Offering 3 flights every month between Chicago and Grand Cayman, they'll make sure your journey is just as good as the destination.

Route Information for Flights from Chicago to Grand Cayman

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

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Plan Your Trip from Chicago to Grand Cayman

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

Owen Roberts International Airport

If you're looking for a bargain on flights to Grand Cayman Island, Orbitz.com can help you. The website searches flights from numerous airlines so that you can choose tickets that fit your budget. The Owen Roberts International Airport is the main international airport for the Cayman Islands. It's located on Grand Cayman Island-the largest of the three islands-on Roberts Drive, approximately one mile from the center of George Town. Eleven airlines service the airport, including United Airlines, Delta Air Lines, Cayman Airways and American Airlines.

Transportation From the Airport

Taxicabs are available at the airport on a first-come, first-served basis. Cab fare ranges from $12 to $70, depending on what part of Grand Cayman Island you're visiting. Cab fare into George Town averages between $15 and $18. Limousines and buses also transport passengers from the airport, but they require reservations. If you want access to your own vehicle, you can purchase a vacation package that includes car rental and flight from Orbtiz.com.

Grand Cayman Island Climate

Even though the temperatures in the Grand Cayman Islands range from the low 70s to the low 90s all year long, the weather determines the peak travel season. The off-peak travel season runs from May to November, because the islands have more rainfall during this time. If you use Orbitz.com to book your trip during the off-peak season, you'll save money on your travel expenses.

Highlights and Attractions

The Cayman Motor Museum, Dolphin Cove, Kittiwake Shipwreck & Artificial Reef and Seven Mile Beach are some of the top tourist attractions on Grand Cayman Island. In addition to finding flights to Grand Cayman Island, Orbitz.com can help you purchase tickets to local attractions and arrange guided 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.