Flights
Hotels
From
To
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.
Flights
Hotels
Round-trip
One-way
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.

Cheap Flights From Chicago To Massachusetts Last modified: Jul 29, 2016 12:50 AM

Cheap flights from Chicago (CHI) to popular destinations in Massachusetts (MA)

Boston
Carrier Departure Date Return Date Lowest Price
United Oct 29, 2016 Nov 2, 2016 $77
United Sep 10, 2016 Sep 20, 2016 $77
United Sep 13, 2016 Sep 17, 2016 $77
United Sep 20, 2016 Sep 24, 2016 $77
United Oct 18, 2016 Oct 26, 2016 $77
United Oct 26, 2016 Oct 29, 2016 $78
United Oct 25, 2016 Nov 8, 2016 $83
United Sep 14, 2016 Sep 21, 2016 $83
United Sep 21, 2016 Sep 24, 2016 $83
United Oct 25, 2016 Oct 29, 2016 $83
Hyannis
Carrier Departure Date Return Date Lowest Price
American Aug 19, 2016 Aug 28, 2016 $418
American Aug 19, 2016 Aug 22, 2016 $457
United Aug 19, 2016 Aug 22, 2016 $475
United Aug 19, 2016 Aug 28, 2016 $482
United Aug 25, 2016 Aug 28, 2016 $515
American Sep 23, 2016 Oct 2, 2016 $532
United Sep 16, 2016 Sep 25, 2016 $538
American Aug 25, 2016 Aug 28, 2016 $549
United Sep 17, 2016 Sep 25, 2016 $571
United Oct 12, 2016 Oct 16, 2016 $580
Martha's Vineyard
Carrier Departure Date Return Date Lowest Price
American Aug 19, 2016 Aug 28, 2016 $311
American Aug 18, 2016 Aug 27, 2016 $418
American Sep 11, 2016 Sep 17, 2016 $557
United Sep 11, 2016 Sep 17, 2016 $575
United Aug 18, 2016 Aug 27, 2016 $580
JetBlue Aug 18, 2016 Aug 27, 2016 $598
United Aug 7, 2016 Aug 9, 2016 $610
Nantucket
Carrier Departure Date Return Date Lowest Price
American Aug 7, 2016 Aug 13, 2016 $272
American Aug 27, 2016 Sep 3, 2016 $272
United Aug 7, 2016 Aug 13, 2016 $344
United Aug 27, 2016 Sep 3, 2016 $359
JetBlue Aug 28, 2016 Aug 31, 2016 $395
United Aug 28, 2016 Aug 31, 2016 $398
American Aug 28, 2016 Aug 31, 2016 $405
United Aug 11, 2016 Aug 18, 2016 $421

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Chicago to Massachusetts

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Chicago to Massachusetts.

DestinationDepartingReturningPrice
Boston 8/26/16 8/30/16 $157

Flight Schedule Summaries Number of flights searched: 259Last modified: Jul 29, 2016 12:50 AM

Chicago to Nantucket
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American DCA X X
JetBlue JFK X X X X X X X
Chicago to Boston
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X X
American DCA X
JetBlue - X X X X X X X
JetBlue JFK X X X X X X X
Delta ATL X X X X X X X
Spirit - X X X X X X X
United - X X X X X X X
United IAD X X X X X X X
Southwest - X X X X X X X
Southwest CMH X X X X X X X
Chicago to Martha's Vineyard
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American LGA X X
American PHL / DCA X X
JetBlue BOS X X X X X X X
Delta JFK X X X X X X X
Delta CVG / JFK X X X X

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Boston American, Alaska, JetBlue, Spirit, United $77
Chicago to Martha's Vineyard American, JetBlue, United $311
Chicago to Nantucket American, JetBlue, United $272
Chicago to Hyannis American, JetBlue, United $418

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Sao Luiz American, Azul, Latam Airlines Brasil, United Check Dates

Cheap Domestic Flights to Massachusetts - MA

FlightsAirlineLowest Price
Indianapolis to Boston American, Alaska, United $177
Milwaukee to Boston American, Alaska, United $164
Madison to Boston American, Alaska, United $325
Green Bay to Boston American, Alaska, United $372
Moline to Boston American, United $250
Lansing to Boston American, Alaska, United $254
Appleton to Boston United $372
Grand Rapids to Boston American, Alaska, United $210
Kalamazoo to Boston American, United $260
Peoria to Boston American, United $250
Bloomington - Normal to Boston American $244
South Bend to Boston United $364
Champaign to Boston American $330
Ft Wayne to Boston American, Alaska, United $336
Dubuque to Boston American $299
Springfield to Boston American, United $250
Toledo to Boston American $254
Indianapolis to Nantucket American, United Check Dates
Indianapolis to Martha's Vineyard American, United Check Dates
Milwaukee to Nantucket American, United $555
Milwaukee to Martha's Vineyard American, United $824
Grand Rapids to Nantucket American, United Check Dates
Milwaukee to HyannisCheck Dates
Cheap Flights from Chicago to Massachusetts - from $77 Round trip from CHI to MA