Cheap flights from Madison to Chicago from $249

Traveling between Madison 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 Madison. The main one is Dane County Regional and other nearby airports include O Hare International, Chicago Midway International, Appleton International, Chicago Rockford International, The Eastern Iowa, Dane County Regional, La Crosse Regional, General Mitchell International, Quad City International, Green Bay–Austin Straubel International

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