Travel options for:
Windsor to Chicago
  • Bus

    $29 - $75
    1. Windsor, ON

      5 h 49 min - once daily

      $29 - $75

  • Train

    $52 - $132
    1. Jefferson & Randolph

      20 min - every 20 minutes - line 053

      $2

    2. Detroit Amtrak

      5 h 18 min - once daily

      $50 - $130

  • Drive

    $35 - $55
    1. Windsor

      4 h 44 min - 286.1 miles

      $35 - $55

  • Fly Detroit to Chicago Midway

    $126 - $268
    1. Windsor

      25 min - hourly

      $1 - $2

    2. Outer Dr & Edsel

      45 min - every 2 hours - line 125

      $2

    3. Detroit (DTW)

      1 h 10 min - non-stop

      $120 - $260

    4. Chicago Midway (MDW)

      24 min - every 15 minutes

      $2 - $4

  • Fly Detroit to Chicago O'Hare

    $116 - $319
    1. Windsor

      25 min - hourly

      $1 - $2

    2. Outer Dr & Edsel

      45 min - every 2 hours - line 125

      $2

    3. Detroit (DTW)

      1 h 16 min - non-stop

      $110 - $310

    4. Chicago O'Hare (ORD)

      42 min - every 10 minutes

      $2 - $5

  • Fly Detroit to South Bend, train

    $214 - $1,219
    1. Windsor

      25 min - hourly

      $1 - $2

    2. Outer Dr & Edsel

      45 min - every 2 hours - line 125

      $2

    3. Detroit (DTW)

      1 h 3 min - non-stop

      $200 - $1,200

    4. South Bend (SBN)

      2 h 26 min - hourly

      $11 - $15

  • Bus to Toledo, fly to Chicago O'Hare

    $130 - $378
    1. Windsor

      1 h 17 min - twice daily

      $13 - $35

    2. Toledo

      21 min - 20.2 miles

      $35 - $50

    3. Toledo (TOL)

      1 h 9 min - non-stop

      $80 - $290

    4. Chicago O'Hare (ORD)

      42 min - every 10 minutes

      $2 - $5

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From Windsor, ON bus to Chicago, IL. 5 h 49 min $64. From Jefferson & Randolph line 053 bus to Detroit Amtrak then train to Chicago Union Station Amtrak. 6 h 38 min $122. From Windsor drive to Chicago. 4 h 44 min $58. From Fort & 6Th bus to Outer Dr & Edsel, line 125 bus to Detroit airport, fly to Chicago Midway airport, then subway to Chicago. 4 h 11 min $263. From Fort & 6Th bus to Outer Dr & Edsel, line 125 bus to Detroit airport, fly to Chicago O'Hare airport, then subway to Chicago. 4 h 34 min $227. From Fort & 6Th bus to Outer Dr & Edsel, line 125 bus to Detroit airport, fly to South Bend airport, then train to Chicago. 6 h 17 min $782. From Detroit, MI bus to Toledo, taxi to Toledo airport, fly to Chicago O'Hare airport, then subway to Chicago. 4 h 34 min $411.