awe, come on, you've been around long enough to know that it's not typical for T/S to be in major cities, though I've seen a lot of requests for Chicago over the years.
ORD is a different hotel market than downtown Chicago, though both are popular in their own ways. I've had business overnights at both, along with seminars near ORD, and put up by the airline, too.
Downtown Chicago is a popular with both families and couples. Theatre, fine dining, museums, baseball, loads to do! It's more accessible and walkable than NYC. A very popular Midwest destination. So, yes! very much a tourist destination. I've run into foreign travelers there to see Frank Lloyd Wright's home, and families from my neighborhood on school breaks - same as Orlando. Yeah, you might think fall break would be a good time to run up there and then you realize everyone else decided to do that, too.