I can give my two cents on this...
My situation may be slightly different from others as I am only looking for part-time work, but within the city limits all I can say is good luck. I've mainly been looking for hospital positions, and unless you have a strong connection or previous pharmacist experience/residency, you're fighting a hugely uphill battle. I interned at a major hospital throughout school and was a hospital tech through most of undergrad, but it's not really doing me any good. It truly is about who you know, and as I put almost all of my networking effort into my main career route which is non-traditional, my connections for the hospital staffing route are somewhat weaker. As for retail, there are a handful from my class that interned at major chains throughout school (and some before) that ended up getting hired on in the city, with the majority of the rest being hired on as floaters around the burbs. That's not necessarily so terrible, except that some of the floaters have to travel ridiculous distances. I know of one guy who is basically covering the entirety of northern Illinois.
That being said, people are having a little bit better luck out in the far suburbs, so if you don't mind being an hour out from the city it may still be possible to find something.
I'm doing a research fellowship full-time, so I haven't looked for work quite as aggressively as those who are looking for full-time pharmacist positions, but so far I've applied to around a dozen or so places and have had one interview. I followed up about three weeks after the interview (which went very well), but they said they were still interviewing and had "many, many applicants", so I'm not holding my breath.
I'm far from a doom and gloomer, but if you're still in school and looking in the Chicago area, I would say to be realistic and plan on moving.
This applies to new grads only though. I'm seeing a ton of openings for DOP positions if you qualify for that.
