RV will be very costly, you will probably be given only 200km a day, then $0.50 a km afterwards, not to mention the cost of gas for an RV.....
I don't know of any company that will let you pick up an RV in Tornoto and drop it off in Chicago. One-Way rentals are difficult enough to find.... let alone a one-way rental between 2 countries.
Several years ago, I took an RV trip (my own vehicle though) from Ottawa to Winnipeg... and stayed in downtown Chicago for a couple of days at a hotel. I'd called beforehand to ensure there was surface RV parking nearby and didn't have any problem driving into the city and parking for 2 nights.
I wouldn't want to get lost in a city in an RV, but with a little planning ahead it's quite doable.
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