How could i hitchhike from Connecticut(close to NYC) to Illinois?

Well I've always wanted to go on hitchhiking to a place that is decently far, but before I head to Cali haha I thought visiting a friend up in Chicago might be a great experience. I haven't done much research yet, but I am genuinely interested in doing it. Somebody told me that it was illegal to hitchhike nowadays or that truck companies had policies against it, but I'm willing to walk a good amount of the way if necessary. So my main question is what is the best way to snag a ride heading to Chicago, as I would think there would be trucks heading to a big city as Chicago is. But What would you guys recommend? What should I take on my trip? I plan on making it to my destination in a minimum of 2days - and max of 6 days, if I'm not close or halfway by 3 days i'm heading back home. Would rest spots be a good place to look for a ride to hitch or is that sketchy? Any recommendations or suggestions are very much appreciated. Please no trolling, unless if its completely hysterical. Thank you