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Cheap Flights from Boston to Chicago - BOS to CHI (reverse)

Popular Flights from Boston to Chicago

  • Airfare from Boston to Chicago on Spirit from $158 round trip
  • Airfare from Boston to Chicago on American from $186 round trip
  • Airfare from Boston to Chicago on JetBlue from $186 round trip
  • Airfare from Boston to Chicago on United from $186 round trip
  • Airfare from Boston to Chicago on US Airways from $208 round trip

Did You Know?

  • 14 airlines operate between Boston, MA and Chicago, IL
  • Continental has the most nonstop flights between Boston, MA and Chicago, IL.
  • The shortest flight between Boston, MA and Chicago, IL on Virgin America is 4,344 miles.
  • 168,107 seats are available per day to fly out of Boston, MA connecting to Chicago, IL
  • New York, NY is the most popular connection for one stop flights between Boston, MA and Chicago, IL.
  • The largest aircraft operated by WestJet flying between Boston, MA and Chicago, IL is a ERJ with 37 seats.
  • The smallest aircraft operated by Copa flying between Boston, MA and Chicago, IL is a 737 with 114 seats.
  • All Nippon has 3 nonstop flights between Boston, MA and Chicago, IL.

Advance Purchase Prices from Boston to Chicago

  • Carrier
    0 Days
    1 Day
    3 Days
    7 Days
    10 Days
    14 Days
    21 Days
  • AirTran
    $533
    $533
    $371
    $209
    $209
    $213
    $213
  • Alaska
    $2996
    $2996
    $2996
    $2996
    $2996
    $2996
    $2996
  • American
    $176
    $176
    $342
    $180
    $180
    $184
    $184
  • Continental
    $176
    $176
    $432
    $180
    $180
    $184
    $184
  • Delta
    $381
    $381
    $453
    $393
    $393
    $205
    $205
  • JetBlue
    $176
    $176
    $342
    $180
    $180
    $184
    $184
  • Spirit
    $124
    $124
    $124
    $86
    $86
    $86
    $86
  • US Airways
    $270
    $270
    $432
    $180
    $180
    $184
    $184
  • United
    $176
    $176
    $342
    $180
    $180
    $184
    $184

Daily Non-stop Flight Schedules from Logan International to Chicago Midway

  • Airline
    Mon
    Tue
    Wed
    Thu
    Fri
    Sat
    Sun
    Earliest Flight
    Latest Flight
  • Southwest
    3
    3
    3
    3
    3
    2
    2
    6:00 AM
    4:25 PM

Daily Non-stop Flight Schedules from Logan International to O Hare

  • Airline
    Mon
    Tue
    Wed
    Thu
    Fri
    Sat
    Sun
    Earliest Flight
    Latest Flight
  • American
    8
    8
    8
    8
    8
    6
    7
    6:10 AM
    7:25 PM
  • JetBlue
    3
    3
    3
    3
    3
    1
    3
    8:10 AM
    4:04 PM
  • United
    7
    6
    6
    7
    7
    6
    7
    6:45 AM
    5:31 PM

Cheap Domestic Flights from Boston - BOS

Flights
Airline
Lowest Price
Alaska, American, US Airways, Sun Ctry, Spirit, Hawaiian, JetBlue, Virgin America, AirTran, Delta, United
$256
United, American, Delta, AirTran, JetBlue, US Airways
$118
Sun Ctry, US Airways, American, Hawaiian, Delta, JetBlue, Virgin America, Alaska, United, AirTran
$231
AirTran, JetBlue, Delta, Virgin America, Spirit, United, Sun Ctry, US Airways, American, Alaska
$226
American, Delta, United, US Airways, Spirit, JetBlue, AirTran
$218
Delta, US Airways, United, American
$225
American, Spirit, AirTran, US Airways, Delta, United
$150
United, US Airways, American, JetBlue, Alaska
$150
United, US Airways, American, Spirit, JetBlue, AirTran, Delta
$148
JetBlue, Sun Ctry, American, US Airways, United, Delta, Spirit
$148
AirTran, JetBlue, Spirit, US Airways, American, Delta, United
$171
US Airways, United, Delta, JetBlue
$110
United, AirTran, Spirit, JetBlue, US Airways, American, Delta
$156
US Airways, American, Alaska, United, Delta, Spirit, AirTran, JetBlue
$218
JetBlue, United, US Airways, American, AirTran, Delta
$98
US Airways, United, Delta, JetBlue, AirTran, American
$197
Delta, United, Spirit, American, JetBlue, Virgin America, AirTran, US Airways, Sun Ctry, Alaska
$270
United, AirTran, Virgin America, JetBlue, Sun Ctry, American, US Airways, Alaska, Delta
$222
American, JetBlue, AirTran, US Airways, United, Delta
$208
Alaska, AirTran, United, Delta, US Airways, American, Sun Ctry, JetBlue
$219
United, American, AirTran, JetBlue, Delta, US Airways
$198
Spirit, US Airways, Delta, United
$88
United, US Airways, JetBlue
$148
AirTran, US Airways, JetBlue, American, Delta, United
$148
American, United, US Airways, AirTran, Sun Ctry, Spirit, Delta
$243
Delta, American, US Airways, Spirit, JetBlue, AirTran, United
$188
AirTran, Alaska, United, Delta, US Airways, American, JetBlue
$178
United, Delta, US Airways, JetBlue, AirTran
$118
American, AirTran, United, Delta, US Airways, Spirit, JetBlue
$333
AirTran, United, Delta, American, US Airways, JetBlue
$127
JetBlue, Delta, AirTran, United, US Airways
$130
Delta, Alaska, United, AirTran, Virgin America, JetBlue, US Airways, American
$226
Spirit, US Airways, Alaska, United, Delta, American, JetBlue, Virgin America, AirTran
$244
Delta, US Airways, United, Hawaiian, American, Alaska
$688
AirTran, JetBlue, United, Delta, US Airways, American
$194
American, US Airways, Delta, United, Spirit, JetBlue, AirTran
$141
United, Delta, JetBlue, US Airways
$220
JetBlue, US Airways, United, American, Delta, Spirit
$256
AirTran, American, US Airways, Delta, United
$361
United, US Airways, AirTran, JetBlue, American, Delta
$170
Delta, US Airways, JetBlue, AirTran, United
$144
Cheap Flights from Boston to Chicago, from $158 Round trip from BOS to CHI