Matt: Do you have a soft top now, or just a hardtop? If you have soft top hardware already, then you have some extra options (Sailcloth Replace-A-top, that Shiny mentions). But you can't use that unless you already have hardware.
The Pavement Ends top uses the same hardware design as the Supertop, so it's exactly the same for ease of use. Think of Pavement Ends as a Supertop that has cut some corners: it's made in China from less expensive fabric, it has thinner window glass. I think it's still a quality product, ESPECIALLY when you are comparing it to other budget soft tops.
The Sunrider top is very much like a Supertop with an extra hinge. It allows the front part to flip back. It adds some complexity, but otherwise uses the same concepts and technology of a Supertop. Pavement Ends also offers a budget version of this top.
Standing up to Chicago weather?
I agree with Brent, that you need to keep your expectations in check. But any of the tops should work fine, especially a new one with new hardware. Adjusted properly, they will shed snow and water with no troubles. Seal the seams, keep it tight, and you'll be fine.
I'd recommend the Bestop Supertop. But then, I would, wouldn't I?