Truck to Winnipeg
If it were us, we would ship it LTL on either a stepdeck, double drop, or RGN.
Rate to Winnipeg from TO would be somewhere around $1,700 - $2,000.00 range (as long as its not wide), depending on who you use.
Let me know if you need help and I'll put you in touch with some o9f the guys that run that lane.