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I have an aunt and uncle in San Francisco (more precisely Mountain View), and I currently am in Toronto, planning a road trip starting mid-August to drive down to San Francisco.
Basically, I will spend the first night in Chicago for sure, but I don't know of any cities along the way after Chicago which I should stop. I am just hoping to stop for two nights (one in Chicago and the other night somewhere else) before making it to San Francisco.
Is that possible?
No - It's not possible.
Toronto to Chicago is very feasable. Its a fairly pleasant 500 miles. I've made the drive myself more than a few times, and its a long day on the road, but still comfortable.
Chicago to San Francisco is more than 2100 miles. There simply is no way you can safely drive this distance in two days. You'd be looking at driving 19 hours a day for two days in a row.
Even over 3 full days on the road from Chicago to SF, you'd be pushing the extremes of physical limitations for a solo traveler, and would require more driving than we'd recommend.
Either give yourself more time for this trip or look at getting an airline ticket.