Cheap flights from Chicago to Grand Cayman from $138

Travelers frequently search for route combinations, such as Chicago and Mexico City, Guadalajara, Morelia, New York, León, Orlando, Las Vegas, Dallas, Houston, Tampa, Los Angeles, Miami, Phoenix, Denver, Monterrey, Cancún, Istanbul, Puerto Vallarta, Atlanta, Calgary.

Travelers frequently search for route combinations, such as Grand Cayman and Miami, Houston, Denver, Philadelphia, Washington, D.C., Minneapolis, Toronto, Mexico City, Panama, Guadalajara, Bucharest, Manila, Saint Lucia, Key West, Fort Myers, San Juan, Fort Lauderdale, Little Rock, Norfolk, Medford.

Chicago is mainly served by O Hare International. But there are other airports nearby, including Chicago Midway International, Chicago Rockford International.

The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, South Bend International, Dane County Regional, General Mitchell International, General Wayne A. Downing Peoria International, Fort Wayne International, Quad City International, Central Illinois Regional, Muskegon County, University of Illinois Willard.

The main airport in Grand Cayman is Owen Roberts International. It is also served by Owen Roberts International.

Currently, you can fly between Chicago and Grand Cayman with Cayman Airways, Frontier Airlines, Spirit Airlines, JetBlue Airways, United Airlines.

If you don’t have specific dates for your trip between Chicago and Grand Cayman, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

Traveling between Chicago and Grand Cayman, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What’s more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

There are a number of airports in and around Chicago. The main one is O Hare International and other nearby airports include Gerald R. Ford International, South Bend International, Dane County Regional, General Mitchell International, General Wayne A. Downing Peoria International, Fort Wayne International, Quad City International, Central Illinois Regional, Muskegon County, University of Illinois Willard