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Cheap Flights from Chicago to Massachusetts

Popular Flights from Chicago to Massachusetts

Did You Know?

  • The earliest flight from Chicago, IL leaves at 1:00 am.
  • There are 74 connecting cities from Chicago, IL to Massachusetts.
  • There are 431 direct flights from Chicago to Massachusetts.
  • The most popular destination from Chicago, IL is La Guardia.
  • New York, NY is the most popular connecting city from Chicago, IL to Massachusetts.
  • There are 30 carriers flying into Massachusetts.
  • The longest flight from Chicago, IL to Massachusetts is 864 miles.
  • The shortest flight from Chicago, IL to Massachusetts is 864 miles.

Cheap Domestic Flights from Chicago - CHI

Flights
Airline
Lowest Price
US Airways, Delta, United, Alaska, Spirit, JetBlue, AirTran, American
$168
Cheap Flights from Chicago to Massachusetts - from $168 Round trip from CHI to MA