Cheap flights from Chicago to Anguilla from $338

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 Anguilla and Phoenix, Los Angeles, Honolulu, Atlanta, Cleveland, Washington, D.C., Fort Lauderdale, Antigua, Boston, Philadelphia, Seattle, Orlando, Miami, New York, Tampa, Cincinnati, Lower Prince's Quarter, Dallas, San Juan, Houston.

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, General Mitchell International, South Bend International, Dane County Regional, General Wayne A. Downing Peoria International, Fort Wayne International, Quad City International, Muskegon County, Central Illinois Regional, University of Illinois Willard.

The main airport in Anguilla is Clayton J. Lloyd International. It is also served by Clayton J. Lloyd International.

Currently, you can fly between Chicago and Anguilla with Anguilla Air Services, Spirit Airlines, JetBlue Airways, Frontier Airlines, Tradewind Aviation.

If you don’t have specific dates for your trip between Chicago and Anguilla, 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 Anguilla, 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, General Mitchell International, South Bend International, Dane County Regional, General Wayne A. Downing Peoria International, Fort Wayne International, Quad City International, Muskegon County, Central Illinois Regional, University of Illinois Willard