Go to the school. Visit it. Talk to the administration. Meet with a professor. Talk to the students. Compare the fields of law you're interested in, and see how many of their grads go into those fields...you can find this info by looking up stats, talking to alum, talking to the career services office, etc.
Do this, and you'll know if you're "comfortable" with that school.
I have done all of this. The faculty seem more engaging at Cinci, the students are happier at DePaul, the aesthetics of the law school are better at DePaul, the employment at graduation is better at DePaul, the overall employment is better at Cinci, the IP prospects are better at DePaul, the likelihood of IP employment is better at Cinci, career services is about the same at both, and the collaborative nature is better at Cinci. While DePaul would have more networking opportunities, I likely would not have enough time to utilize all of them - so the the nuber of networking events I could attend are likely to be similar (based on what IP students at both schools tell me). The edge in quality of event might go to DePaul, but there will be more IP students from the other schools there too. It seems that the strengths/weaknesses for each balance the other out and I ought to just flip a coin!
The one thing that is consistent is that alumni from each school, hiring partners at firms, and practicing IP attys not associated with either school all say to put more emphasis on where you want to work - okay, but how to decide that? I have been to both cities several times, and either would be fine. I would be less happy with the quality of apartment in the city of Chicago, but would enjoy the quick commute to school. I would enjoy the quality of apartment in the suburbs of Chicago, but would have a costly (time and money) commute. There is an apartment complex in Cinci that is sufficient and has a free bus to school. UC law school is located at the edge of campus which is not a good neighborhood, but DePaul is in downtown Chicago which is not much better.