Ah, I thought Phase II was out of business, but that's only the Eastside shop. It looks like they're still open in Tosa. They were my go-to for nearly a decade when I lived on the Eastside/Riverwest.
Jamie Thomas was the only person to ever cool-guy me at Uprise. They do have more of a boutique vibe, but they've always gone out of their way to help me get stuff. I first ordered some AWS boards from them in 2010 and they were worried about scuffs, so shipped me a box straight from DNA. I have a ton of stories of them looking out for me.
I'm a more recent FA customer, but they've been really helpful, friendly, and patient with my dumb requests.
I know absolutely nothing about Prosper. Yeah went under about 1-2 years ago. I think those are the only Chicago shops.