Cheap flights from Kailua to Chicago from $226

Traveling between Kailua and Chicago, 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 Kailua. The main one is Kona International and other nearby airports include Kona International, Hilo International, Waimea-Kohala

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

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Kailua, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Kailua, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.