Cheap flights from Boston to Chicago from $82

Traveling between Boston 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 Boston. The main one is Logan International and other nearby airports include Logan International, Bradley International, Rhode Island T. F. Green Int'l Airport, Albany International, Portland International Jetport, Tweed New Haven, Manchester–Boston Regional, Portsmouth International Airport at Pease, Lebanon Municipal, Knox County Regional

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, Fort Wayne International, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, Kalamazoo/Battle Creek International, Muskegon County.

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 Boston, 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 Boston, 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.