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Cheap Flights From Chicago To Massachusetts Last modified: Jul 1, 2016 6:33 PM

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Boston American, Alaska, JetBlue, Spirit, United $81
Chicago to Martha's Vineyard American, JetBlue, United $359
Chicago to Nantucket American, JetBlue, United $272
Chicago to Hyannis American, JetBlue, United $359

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Sao Luiz American, Azul, TAM, United $1,449

Cheap Domestic Flights to Massachusetts - MA

FlightsAirlineLowest Price
Indianapolis to Boston American, Alaska, United $177
Milwaukee to Boston American, Alaska, United $162
Madison to Boston American, Alaska, United $325
Green Bay to Boston American, United $372
Moline to Boston American, Alaska, United $250
Lansing to Boston American, Alaska, United $234
Appleton to Boston United $372
Grand Rapids to Boston American, Alaska, United $214
Kalamazoo to Boston American, United $315
Peoria to Boston American, United $250
Bloomington - Normal to Boston American $244
South Bend to Boston United $393
Champaign to Boston American $360
Ft Wayne to Boston American, Alaska, United $369
Dubuque to Boston American $385
Springfield to Boston American, United $250
Toledo to Boston American $184
Indianapolis to Nantucket American, United $499
Indianapolis to Martha's Vineyard American, United $429
Milwaukee to Nantucket American, United Check Dates
Milwaukee to Martha's Vineyard American, United Check Dates
Grand Rapids to Nantucket American, United Check Dates
Milwaukee to HyannisCheck Dates
Cheap Flights from Chicago to Massachusetts - for Round trips from CHI to MA