Travel options for:
Chicago to Massachusetts
  • Fly Chicago Midway to Boston

    $94 - $388
    1. Chicago

      23 min - every 15 minutes

      $2 - $4

    2. Chicago Midway (MDW)

      2 h 10 min - non-stop

      $90 - $380

    3. Boston (BOS)

      8 min - every 15 minutes

      $0

    4. Airport - Inbound

      5 min - every 10 minutes

      $2 - $4

  • Fly Chicago O'Hare to Boston

    $79 - $269
    1. Chicago

      43 min - every 10 minutes

      $2 - $5

    2. Chicago O'Hare (ORD)

      2 h 8 min - non-stop

      $75 - $260

    3. Boston (BOS)

      8 min - every 15 minutes

      $0

    4. Airport - Inbound

      5 min - every 10 minutes

      $2 - $4

  • Fly Chicago Midway to Hartford

    $183 - $445
    1. Chicago

      23 min - every 15 minutes

      $2 - $4

    2. Chicago Midway (MDW)

      1 h 55 min - non-stop

      $170 - $410

    3. Hartford (BDL)

      34 min - hourly - line 30

      $1 - $4

    4. Harford, CT - Union Station

      35 min - every 2 hours

      $10 - $27

  • Fly Chicago O'Hare to Hartford

    $173 - $386
    1. Chicago

      43 min - every 10 minutes

      $2 - $5

    2. Chicago O'Hare (ORD)

      2 h 2 min - non-stop

      $160 - $350

    3. Hartford (BDL)

      34 min - hourly - line 30

      $1 - $4

    4. Harford, CT - Union Station

      35 min - every 2 hours

      $10 - $27

  • Fly Chicago Midway to Providence

    $115 - $351
    1. Chicago

      23 min - every 15 minutes

      $2 - $4

    2. Chicago Midway (MDW)

      2 h - non-stop

      $100 - $330

    3. Providence (PVD)

      34 min - hourly - line 20

      $2

    4. Kennedy Plaza

      6 min - 1883 feet

    5. Providence, RI

      25 min - every 4 hours

      $11 - $15

  • Bus

    $102 - $204
    1. Chicago, IL

      14 h 30 min - every 4 hours

      $75 - $180

    2. New York

      4 h 30 min - hourly

      $25

  • Train

    $130 - $390
    1. Chicago Union Station Amtrak

      21 h 31 min - once daily

      $130 - $390

  • Drive

    $95 - $150
    1. Chicago

      16 h 31 min - 996.8 miles

      $95 - $150

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From Adams/Wabash subway to Chicago Midway airport, fly to Boston airport, bus to Airport - Inbound, then subway to Boston. 3 h 52 min $166. From Jackson-Blue subway to Chicago O'Hare airport, fly to Boston airport, bus to Airport - Inbound, then subway to Boston. 4 h 10 min $147. From Adams/Wabash subway to Chicago Midway airport, fly to Hartford airport, line 30 bus to Harford, CT - Union Station, then bus to Springfield. 5 h 20 min $249. From Jackson-Blue subway to Chicago O'Hare airport, fly to Hartford airport, line 30 bus to Harford, CT - Union Station, then bus to Springfield. 5 h 47 min $230. From Adams/Wabash subway to Chicago Midway airport, fly to Providence airport, line 20 bus to Kennedy Plaza, walk to Providence, RI, then bus to Fall River. 5 h 47 min $200. From Chicago, IL bus to New York then bus to Boston, MA. 19 h 51 min $115. From Chicago Union Station Amtrak train to Boston South Station Amtrak. 21 h 31 min $281. From Chicago drive to Boston. 16 h 31 min $119.

 
 

Train, bus or fly from Chicago to Massachusetts?

Southwest Airlines, Porter Airlines and Delta fly from Chicago to Boston hourly. Alternatively, Greyhound USA operates a bus from Chicago to Boston every 4 hours. Tickets cost $75 - $180 and the journey takes 14 h 30 min. 2 other operators also service this route.