Take heart! Here's an article from the Chicago Maroon, which indicated that U/C expects to accept students from the wait list. Unfortunately it doesn't answer your questions about when you will hear. But hopefully this will help!
Chicago Maroon | U of C acceptance rate hits record low
"With mounting competition for limited admissions spots both at the U of C and other schools, the question of this year’s class yield—how many accepted students will decide to come to the University—is a particular concern for admissions officers.
'Because the group we admitted is so strong, I’d imagine they have lots of attractive offers, particularly from the Ivies,' [Michael] Behnke [Vice President and Dean of Enrollment] said. 'Harvard and Yale were even more generous to upper-income families than the Odyssey Program' which eliminates the family tuition contributions for students from families earning less than $60,000 per year.
Due to the uncertain yield, there is a relatively large waitlist of 1,200 students, compared to 800 students last year. The unusually large list stems from a pervasive caution in admissions offices in highly selective institutions.
'When you have such a selective institution and you’re looking at students that are going to get offers from other places, you have to be cautious,' Behnke said. 'I’d be shocked if we didn’t take students [from the waitlist] this year.'"