My advice would be, go for it! The Chicago Greeter Program is free and has a strict non-tipping policy. Through this and other feedback cycles, the organizers can make sure that all volunteer greeters do this out of genuine enjoyment. Through some questions, they try to pair you up with a volunteer who matches your interests and plans. My experience was very positive. Bernhard Schmitz took me on a general and architectural walking tour through the city center. I found him extremely knowledgeable. He made me see things I would not notice and also took me into many buildings I would not normally just enter as a tourist. I took his knowledge with me throughout the rest of my stay in Chicago, but also on my subsequent trip to New York.
I would therefore recommend anyone to book a greeter early in your stay. It is a wonderful experience and their wisdom will also make the rest of your trip more worthwhile.
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