Closest I ever got to Chicago was landing at the airport, when I had to go to Lombard for some computer training.
I landed at O'Hare, and tried like crazy to finds a cab. I was checking with every cab company about the cost to take me to my hotel, and got back everything from $150 and up.
Then this guy walks in, with this thick NY type accent, yelling out "Hey, who needs a limo?" He looks at me and asks if I need a limo, and just for grins I asked him how much to Lombard. He said "$75". Before he could take a step, I said "sold!".
He drove like a maniac, and I legitimately feared for my life as he cut in, out, and all around traffic, but he got me to my hotel in one piece.
Anyway, I stayed at the LaQuinta in Lombard, and since my meals were paid for, I went to this steakhouse that was a few blocks from the hotel. It was pricey .... but I wasn't paying .... and the steak was so delicious I went back again the next day. (on the company tab, of course)
I wish I could remember the name of the restaurant, but it's been a couple of decades, and the memory isn't what it once was.