People still weren't responding. They totally ignored me after they read my sign. The only verbal “no” I got was from a very good-looking French couple. I decided to switch locations. As I walked down the sidewalk, a gentleman who was on his cell phone held up a finger at me, an indication that he was interested.
He finished his call and asked me what the deal was. I gave him my pitch and asked him where he was from. He had just moved here from Dallas, and wanted to go on the tour so he could learn more about Chicago. “A perfect candidate,” I thought to myself, as I tried to sell the tour as best as I could. Then he asked how it would be conducted.
“Oh, in my Jeep. Top down of course,” I replied cleverly.
This is when I lost the guy. He looked at me funny, wished me luck, and he was gone. I guess he didn't feel comfortable riding around a new city in a car with a total stranger.
A few minutes later, I was approached by a lady from Argentina.
“When do the boat tours start?” she asked.
“Umm … this isn't a boat tour. I'm not affiliated with them,” I answered, “Yet.”
“Oh. Well, do you know when they start, because I really want to take one of those.”
I told her that I didn't know, and then since I had her attention, I gave her my pitch. I told her about the Cook County Tour Guide test, and then explained my theory on visiting anywhere new.
It was all going fine, and she was an incredibly sweet lady until I said that the tours were conducted from my vehicle. She looked at me like I had just shot her horse. Denied again.
What was the deal here? Why weren't people willing to take a little risk? Yes, I am a stranger, but it's not like I'm kidnapping them. Even if I was, they probably had cell phones that they could use to alert the proper authorities. These people were visiting Chicago and missing out on some of the best-kept secrets that only locals know about.
When I came up with this idea, I decided that the tour was going to be the route I drive when I need to think, which I take very often: south on Lakeshore, over to Michigan Avenue, up to Chicago, up Rush to Division, over to Wells, up to Lincoln, over on Armitage to Sheffield, up to Wrigley, then back south on Clark street, past Lincoln Park and the zoo and finally ending up where I started.
No, they wouldn't get to see every part of the city, but there are a million and one sights along that route. What they would see is my Chicago. They would be visiting places and hearing anecdotes about memorable things that happened to me, or learning why I like to go to a certain spot, or seeing places where I think the view of the city is breathtaking. They probably wouldn't even care that this was all being conducted by a stranger from his jalopy of a car.
Think about it: if you were visiting New York , wouldn't it be much more fun and interesting to get a tour from a local? I would much rather do that then pay $25 for a tour of places everybody already knows about.
Frustrated and about to give up, I was approached by a guy who asked me what the catch was. “No catch,” I told him. I gave him my pitch to no avail. He was a local who just wanted to know why a kid was on the street with a homemade sign, trying to give a homemade tour.
“You're just trying to pick up girls,” he chuckled. He got me, because I started to laugh out loud. I denied it, but then he told me that he liked my approach and would try it sometime. Then he went on his way.
At the end of the day, I had given absolutely no Free Chicago Architecture tours. I was kind of disappointed; not so much that nobody was willing to get in my car with me, but because all of these visitors were missing out on a fun and informative, yet very different view of the city.
Hopefully the next time I'm visiting a place I don't know much about, I will see a crazy young man tapping his Free Tour of the City sign. I think that's a tour I'd love to take. 
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