^mominva, my mind first went to your idea ! Chicago is a great place to enjoy architecture. This book looks good.
For comedy, try tickets to Second City, which birthed the original Saturday Night Live cast from Chicago, long ago. If you can give 2 tickets to a show, he can invite someone, which is nice when new to town.
Depending on his interests, there are comedy shows to attend, improv workshops to try one-time (and meet people) on Sundays, or training for business people in their improvisation skills.
Click around their website for Chicago, as they now also have venues in other cities.
The Second City - 50 Years of Funny