Travel options for:
Chicago to Winnipeg
  • Fly from Chicago O'Hare

    $205 - $488
    1. Chicago

      43 min - every 10 minutes

      $2 - $5

    2. Chicago O'Hare (ORD)

      2 h 24 min - non-stop

      $200 - $480

    3. Winnipeg (YWG)

      21 min - hourly - line 15

      $3

  • Fly from Chicago Midway

    $215 - $477
    1. Chicago

      23 min - every 15 minutes

      $2 - $4

    2. Chicago Midway (MDW)

      4 h 2 min - 1 stopover

      $210 - $470

    3. Winnipeg (YWG)

      21 min - hourly - line 15

      $3

  • Bus, Amtrak Thruway

    1. Chicago, IL

      3 h 1 min - once daily

      $35 - $65

    2. Grand Rapids

      22 min - once daily - line 81

      $2 - $5

    3. Rockford, MI

      7 h 53 min - once daily

    4. Sault Ste. Marie, MI

      12 min - 9.3 miles

      $1 - $2

    5. Sault Ste Marie, ON

      21 h 21 min - once daily

      $75 - $180

    6. Southbound Wellington at

      32 min - hourly - line 20

      $3

  • Bus

    $160 - $389
    1. Chicago, IL

      12 h 41 min - once daily

      $55 - $130

    2. Yorkdale, ON

      30 h 38 min - once daily

      $100 - $260

    3. Southbound Wellington at

      21 min - hourly - line 15

      $3

  • Train via Detroit Amtrak

    $302 - $485
    1. Chicago Union Station Amtrak

      5 h 21 min - once daily

      $50 - $130

    2. Detroit Amtrak

      10 min - 7.5 miles

      $1 - $2

    3. Windsor

      4 h 6 min - every 3 hours

      $50 - $75

    4. Toronto, ON

      35 h 39 min - 3 times a week

      $200 - $280

  • Train

    $314 - $550
    1. Chicago Union Station Amtrak

      10 h 16 min - once daily

      $75 - $220

    2. Buffalo

      4 h 31 min - every 3 hours

      $35 - $55

    3. Toronto, ON

      37 h 54 min - 3 times a week

      $200 - $280

  • Drive

    $110 - $170
    1. Chicago

      14 h 37 min - 867.7 miles

      $110 - $170

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From Jackson-Blue subway to Chicago O'Hare airport, fly to Winnipeg airport, then line 15 bus to Winnipeg. 5 h 38 min $267. From Adams/Wabash subway to Chicago Midway airport, fly to Winnipeg airport, then line 15 bus to Winnipeg. 6 h 56 min $266. From Chicago, IL bus to Grand Rapids, line 81 bus to Rockford, MI, Amtrak Thruway to Sault Ste. Marie, MI, drive to Sault Ste Marie, ON, bus to Southbound Wellington at Greyhound Terminal, then line 20 bus to Eastbound Broadway at Osborne. 36 h 30 min. From Chicago, IL bus to Yorkdale, ON, bus to Southbound Wellington at Greyhound Terminal, then line 15 bus to Southbound Vaughan at Portage North. 44 h 50 min $274. From Chicago Union Station Amtrak train to Detroit Amtrak, drive to Windsor, train to Toronto, ON, then train to Winnipeg. 46 h 40 min $398. From Chicago Union Station Amtrak train to Buffalo, train to Toronto, ON, then train to Winnipeg. 2 days 6 h $441. From Chicago drive to Winnipeg. 14 h 37 min $140.