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

    $91 - $261
    1. Philadelphia

      22 min - every 30 minutes

      $8

    2. Philadelphia (PHL)

      2 h 5 min - non-stop

      $80 - $250

    3. Chicago Midway (MDW)

      24 min - every 15 minutes

      $3

      • Chicago
  • Fly Philadelphia to Chicago O'Hare

    $41 - $211
    1. Philadelphia

      22 min - every 30 minutes

      $8

    2. Philadelphia (PHL)

      2 h 2 min - non-stop

      $30 - $200

    3. Chicago O'Hare (ORD)

      42 min - every 10 minutes

      $3

      • Chicago
  • Train to Baltimore, fly to Chicago Midway

    $148 - $324
    1. Philadelphia

      1 h 14 min - 4 times a day

      $65 - $100

    2. BWI Amtrak/MARC Station

      6 min - every 10 minutes

      $0 - $2

    3. Baltimore (BWI)

      2 h - non-stop

      $80 - $220

    4. Chicago Midway (MDW)

      24 min - every 15 minutes

      $3

      • Chicago
  • Train to Newark, fly to Chicago Midway

    $160 - $556
    1. Philadelphia

      1 h 7 min - once daily

      $26 - $65

    2. Newark (EWR)

      2 h 10 min - non-stop

      $130 - $490

    3. Chicago Midway (MDW)

      24 min - every 15 minutes

      $3

      • Chicago
  • Bus Goto Bus

    $90 - $153
    1. Philadelphia, PA

      2 h - hourly

      $12 - $40

    2. New York

      14 h 30 min - twice daily

      $75 - $110

    3. Cermak-Chinatown

      4 min - every 10 minutes

      $3

      • Harrison
  • Train via Washington Union Station Amtrak

    $173 - $258
    1. Philadelphia 30th Street

      1 h 43 min - 4 times a day

      $80 - $120

    2. Washington Union Station

      17 h 40 min - once daily

      $90 - $140

      • Chicago Union Station Amtrak
  • Bus Greyhound USA

    $95 - $218
    1. Philadelphia, PA

      14 h 52 min - once daily

      $70 - $160

    2. Indianapolis, IN

      5 h 11 min - 4 times a day

      $24 - $60

      • Chicago, IL
  • Train

    $110 - $180
    1. Philadelphia 30th Street

      26 h 45 min - 3 times a week

      $110 - $180

      • Chicago Union Station Amtrak
  • Drive

    $75 - $110
    1. Philadelphia

      12 h 27 min - 764.1 miles

      $75 - $110

      • Chicago
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From Suburban Station train to Philadelphia airport, fly to Chicago Midway airport, then subway to Chicago. 3 h 56 min $151. From Suburban Station train to Philadelphia airport, fly to Chicago O'Hare airport, then subway to Chicago. 4 h 10 min $76. From Philadelphia 30th Street Station Amtrak train to BWI Amtrak/MARC Station, bus to Baltimore airport, fly to Chicago Midway airport, then subway to Chicago. 4 h 52 min $223. From Philadelphia 30th Street Station Amtrak train to Newark airport, fly to Chicago Midway airport, then subway to Chicago. 4 h 46 min $223. From Philadelphia, PA bus to New York, bus to Cermak-Chinatown, then subway to Harrison. 17 h 37 min $112. From Philadelphia 30th Street Station Amtrak train to Washington Union Station Amtrak then train to Chicago Union Station Amtrak. 20 h 23 min $258. From Philadelphia, PA bus to Indianapolis, IN then bus to Chicago, IL. 21 h 3 min $154. From Philadelphia 30th Street Station Amtrak train to Chicago Union Station Amtrak. 26 h 45 min $170. From Philadelphia drive to Chicago. 12 h 27 min $91.