Dad:
Mississauga to Chicago is about 500 miles. If you will be loaded both ways, you'll travel 2000 miles each week for $3000 or $1.50 per loaded mile. factor in any deadhead and if it's not excessive, you should do well...IF the promised freight is available EVERY week that you can work. If you are loaded to chicago but empty back to Canada, not counting other deadhead, you will be in the very small minority earning $3.00 a loaded mile. Not a chance unless you are hauling specialty cargo.
Before you enter into an agreement with Kennedy Transport, or any other carrier, do yourself a favor and read the information in the following link:
http://www.ooida.com/Swimming_sharks...owner_ops.html
Come back and visit us if you have any questions with which many of us can help with answers or references to answers.