Chicago: Just The Facts

Cost to get there by car: $110 for gas.
Filled up 3 times.
Total distance: 1710 km
Approx. drive time: 8.5 hours.
We stayed at the Howard Johnson's, right downtown for $100 a night and parked the car at the hotel when we got there and didn't get back in until the trip home. Parking alone was worth the price of the room, But the room was clean and even had free wireless access.
All attractions are either within walking distance or easily accessible by public transit. Taxis were cheap and plentiful and the city felt very safe. People were friendly and helpful. Prices were the same or less than Toronto.
Although, the population of Toronto and Chicago are similar, Toronto is only about a quarter of the size of Chicago. It is the birth place of the skyscraper, and they are everywhere. The architecture is out of this world. Restaurants of all sizes and tastes are everywhere, and the night life is alive with lots to do.
Everything we did from directions to Chicago from Toronto and back again, finding a hotel to stay at, getting around in the city was all accomplished by only using my iPhone, which was an intentional experiment that worked out way better then we expected. (New York City and Boston, our number two and three choices by the way, are also both less than 8 hours drive time as well, according to iPhone. And if iPhone says so, you better believe it will be pretty close).
I highly recommend it to anyone thinking about it. You will not be disappointed.
I give this road trip two thumbs up!