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

    $95 - $406
    1. Boston

      15 min - every 15 minutes

      $2 - $23

    2. Boston (BOS)

      2 h 50 min - non-stop

      $90 - $380

    3. Chicago Midway (MDW)

      24 min - every 15 minutes

      $2 - $4

  • Fly Boston to Chicago O'Hare

    $80 - $287
    1. Boston

      15 min - every 15 minutes

      $2 - $23

    2. Boston (BOS)

      2 h 47 min - non-stop

      $75 - $260

    3. Chicago O'Hare (ORD)

      42 min - every 10 minutes

      $2 - $5

  • Bus to Manchester, fly to Chicago Midway

    $124 - $455
    1. Boston

      1 h 14 min - once daily

      $12 - $35

    2. Manchester (MHT)

      2 h 35 min - non-stop

      $110 - $420

    3. Chicago Midway (MDW)

      24 min - every 15 minutes

      $2 - $4

  • Train to Providence, fly to Chicago Midway

    $165 - $494
    1. Boston

      33 min - 4 times a day

      $60 - $160

    2. Providence Amtrak

      7 min - 2066 feet

    3. Kennedy Plaza

      34 min - hourly - line 20

      $2

    4. Providence (PVD)

      2 h 40 min - non-stop

      $100 - $330

    5. Chicago Midway (MDW)

      24 min - every 15 minutes

      $2 - $4

  • Bus to Hartford, fly to Chicago Midway

    $189 - $460
    1. Boston

      1 h 55 min - every 5 minutes

      $15 - $45

    2. Union Pl and Church St

      35 min - every 2 hours - line 30

      $1 - $4

    3. Hartford (BDL)

      2 h 30 min - non-stop

      $170 - $410

    4. Chicago Midway (MDW)

      24 min - every 15 minutes

      $2 - $4

  • Train to Providence, fly to Chicago O'Hare

    $165 - $645
    1. Boston

      33 min - 4 times a day

      $60 - $160

    2. Providence Amtrak

      7 min - 2066 feet

    3. Kennedy Plaza

      34 min - hourly - line 20

      $2

    4. Providence (PVD)

      2 h 50 min - non-stop

      $100 - $480

    5. Chicago O'Hare (ORD)

      42 min - every 10 minutes

      $2 - $5

  • Bus

    $100 - $205
    1. Boston, MA

      4 h 30 min - hourly

      $25

    2. New York

      14 h 30 min - every 4 hours

      $75 - $180

  • Train

    $130 - $390
    1. Boston South Station Amtrak

      21 h 55 min - once daily

      $130 - $390

  • Drive

    $95 - $140
    1. Boston

      16 h 34 min - 987.4 miles

      $95 - $140

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From South Station Silver Line - Outbound bus to Boston airport, fly to Chicago Midway airport, then subway to Chicago. 4 h 34 min $176. From South Station Silver Line - Outbound bus to Boston airport, fly to Chicago O'Hare airport, then subway to Chicago. 4 h 48 min $157. From Boston, MA bus to Manchester airport, fly to Chicago Midway airport, then subway to Chicago. 5 h 18 min $246. From Boston South Station Amtrak train to Providence Amtrak, walk to Kennedy Plaza, line 20 bus to Providence airport, fly to Chicago Midway airport, then subway to Chicago. 5 h 42 min $323. From Boston, MA - South Station bus to Union Pl and Church St, line 30 bus to Hartford airport, fly to Chicago Midway airport, then subway to Chicago. 6 h 49 min $266. From Boston South Station Amtrak train to Providence Amtrak, walk to Kennedy Plaza, line 20 bus to Providence airport, fly to Chicago O'Hare airport, then subway to Chicago. 6 h 9 min $324. From Boston, MA bus to New York then bus to Chicago, IL. 20 h $115. From Boston South Station Amtrak train to Chicago Union Station Amtrak. 21 h 55 min $281. From Boston drive to Chicago. 16 h 34 min $118.