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Cheap Flights From Chicago To Massachusetts

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

Boston
Carrier Departure Date Return Date Lowest Price
United May 7, 2016 May 10, 2016 $81
United May 14, 2016 May 21, 2016 $81
JetBlue Apr 13, 2016 Apr 26, 2016 $81
United May 7, 2016 May 14, 2016 $81
JetBlue Mar 1, 2016 Mar 9, 2016 $89
United Apr 2, 2016 Apr 5, 2016 $98
United Mar 10, 2016 Mar 19, 2016 $103
United Mar 15, 2016 Mar 16, 2016 $103
United Mar 9, 2016 Mar 15, 2016 $103
United Mar 1, 2016 Mar 2, 2016 $103
Hyannis
Carrier Departure Date Return Date Lowest Price
United Jun 14, 2016 Jun 20, 2016 $492
United Jun 14, 2016 Jun 18, 2016 $492
American Jun 14, 2016 Jun 18, 2016 $492
American Jun 14, 2016 Jun 20, 2016 $492
American Jun 14, 2016 Jun 18, 2016 $506
American Jun 14, 2016 Jun 20, 2016 $506
United Jun 14, 2016 Jun 18, 2016 $526
United Jun 11, 2016 Jun 19, 2016 $536
United Jun 14, 2016 Jun 20, 2016 $536
American May 21, 2016 May 28, 2016 $552
Martha's Vineyard
Carrier Departure Date Return Date Lowest Price
JetBlue Jun 24, 2016 Jun 26, 2016 $377
JetBlue Jun 23, 2016 Jun 26, 2016 $419
JetBlue Aug 6, 2016 Aug 13, 2016 $447
JetBlue Aug 6, 2016 Aug 13, 2016 $454
JetBlue Jun 24, 2016 Jun 26, 2016 $487
JetBlue Jun 23, 2016 Jun 26, 2016 $499
American Jun 21, 2016 Jun 25, 2016 $505
American Jun 21, 2016 Jun 25, 2016 $558
American May 21, 2016 May 28, 2016 $587
American May 21, 2016 May 28, 2016 $590
Nantucket
Carrier Departure Date Return Date Lowest Price
United Jul 8, 2016 Jul 12, 2016 $529
United Feb 17, 2016 Feb 24, 2016 $570
United Feb 17, 2016 Feb 24, 2016 $574
United Jul 8, 2016 Jul 12, 2016 $582
American Feb 17, 2016 Feb 24, 2016 $618
United May 16, 2016 May 20, 2016 $641
American Aug 7, 2016 Aug 14, 2016 $659
American Aug 7, 2016 Aug 14, 2016 $707
American Jul 8, 2016 Jul 12, 2016 $712
American Jul 8, 2016 Jul 12, 2016 $758

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 Fri, Mar 4 Sun, Mar 6 $105

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Boston American, JetBlue, Spirit, United $81
Chicago to Martha's Vineyard American, JetBlue, United $587
Chicago to Nantucket American, JetBlue, United $487
Chicago to Hyannis American, United $407

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Sao Luiz American, Azul, TAM, United Check Dates

Cheap Domestic Flights to Massachusetts - MA

Flight Schedule Summaries

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 LGA X X X X X X X
United - X X X X X X X
United EWR X X X X X X X
Southwest - X X X X X X X
Southwest BWI X X X X X X X
Cheap Flights from Chicago to Massachusetts - from $81 Round trip from CHI to MA