Hi misty: Not sure about Winnipeg but I can tell you that it is about 21 hours from Detroit. We live about 45 minutes from Detroit and drive straight through with 2 drivers. We have found that it is best for us to come home from work, sleep until 1 or 2 am then get up and drive then we are there that evening. We have teens and they stay up to get us up, then sleep in the car until 10:00 am or so, making the drive much shorter for them. We have also left around noon, but then of course arrived around 10:00 am the next day and were unable to check into our hotel until late afternoon.