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: Aug 31, 2016 12:31 AM

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

Boston
Carrier Departure Date Return Date Lowest Price
American Nov 1, 2016 Nov 9, 2016 $77
American Oct 29, 2016 Nov 5, 2016 $77
American Nov 2, 2016 Nov 5, 2016 $77
American Oct 29, 2016 Nov 8, 2016 $77
American Oct 27, 2016 Nov 1, 2016 $77
American Nov 3, 2016 Nov 5, 2016 $77
American Oct 29, 2016 Nov 1, 2016 $77
American Nov 1, 2016 Nov 5, 2016 $77
American Oct 29, 2016 Nov 2, 2016 $77
American Oct 26, 2016 Nov 1, 2016 $77
Martha's Vineyard
Carrier Departure Date Return Date Lowest Price
JetBlue Oct 9, 2016 Oct 16, 2016 $487
American Sep 23, 2016 Sep 25, 2016 $595
American Sep 29, 2016 Oct 3, 2016 $807
JetBlue Nov 18, 2016 Nov 25, 2016 $823
American Oct 14, 2016 Oct 16, 2016 $835
American Nov 18, 2016 Nov 25, 2016 $855
American May 25, 2017 May 29, 2017 $868
American Oct 7, 2016 Oct 9, 2016 $887
Nantucket
Carrier Departure Date Return Date Lowest Price
JetBlue Sep 9, 2016 Sep 13, 2016 $431
American Sep 30, 2016 Oct 2, 2016 $543
JetBlue Sep 30, 2016 Oct 2, 2016 $546
American Sep 27, 2016 Sep 30, 2016 $555
American Sep 9, 2016 Sep 13, 2016 $563
JetBlue Oct 7, 2016 Oct 10, 2016 $589
American Oct 14, 2016 Oct 17, 2016 $594
American Nov 1, 2016 Nov 6, 2016 $635
American Oct 21, 2016 Oct 23, 2016 $646
American Oct 7, 2016 Oct 10, 2016 $655

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 9/22/16 9/27/16 $77

Flight Schedule Summaries Number of flights searched: 222Last modified: Aug 31, 2016 12:31 AM

Chicago to Nantucket
Airline Connections Mon Tue Wed Thu Fri Sat Sun
JetBlue JFK 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 PHL X
JetBlue - X X X X X X X
JetBlue JFK X X X X X X X
Delta DTW X X X X X X X
Spirit - 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 CMH X X X X X X X
Chicago to Martha's Vineyard
Airline Connections Mon Tue Wed Thu Fri Sat Sun
JetBlue BOS X X X X

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Boston American, JetBlue, Delta, Spirit, United $77
Chicago to Martha's Vineyard American, JetBlue, Delta $487
Chicago to Nantucket American, JetBlue, Delta $431
Chicago to HyannisCheck Dates

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Sao Luiz Latam Airlines Brasil $2,724

Cheap Domestic Flights to Massachusetts - MA

FlightsAirlineLowest Price
Indianapolis to Boston American, Alaska, Delta, United $177
Milwaukee to Boston American, Delta, United $281
Madison to Boston American, Alaska, Delta, United $322
Green Bay to Boston American, Delta, United $331
Moline to Boston American, Alaska, Delta, United $256
Lansing to Boston American, Delta, United $248
Appleton to Boston Delta, United $331
Grand Rapids to Boston American, Delta, United $214
Kalamazoo to Boston American, Delta, United $290
Peoria to Boston American, Delta, United $256
Bloomington - Normal to Boston American, Delta $244
South Bend to Boston Delta, United $264
Champaign to Boston American $271
Ft Wayne to Boston American, Delta, United $321
Dubuque to Boston American $321
Springfield to Boston American, United $256
Toledo to Boston American $252
Indianapolis to Nantucket American, Delta Check Dates
Indianapolis to Martha's Vineyard Delta Check Dates
Milwaukee to Nantucket Delta Check Dates
Milwaukee to Martha's Vineyard Delta Check Dates
Grand Rapids to Nantucket American $658
Milwaukee to HyannisCheck Dates
Cheap Flights from Chicago to Massachusetts - from $77 Round trip from CHI to MA