On average, probably often. Shimer College is a small school--there are only 112 undergraduates total, and most students live off-campus.
You might be interested in reading some reviews of this school by current and former students. There are a few online review sites which gather information on student experiences; here are a few reviews which may help paint a picture of what going to this school is like.
"Shimer isn't for everybody...but then again, they don't try to be. No football team, no cheerleaders, no lectures, no memorization, no multiple choice tests, no textbooks, and not many students. But if you want an education that challenges you as you have never been before-and probably never will again--this is the place. And there are no misfits here; or perhaps more accurately, most of us would be misfits at schools with 35,000 students, where athletes are worshipped. Where else do you have dinner, and occasionally class, at your professor's house?" (Read more reviews on Studentsreview.com.)
"The best thing about Shimer are the conversations. Shimer is a very small community, and it can be claustrophobic at times. Fortunately, in the new setting in Chicago, this is less of a concern." (Read more information about this school on Unigo.com.)