I lived in Chicago and paid $1500/mo for a 1500 sq/ft loft in River North, AC, dishwasher, in-unit laundry. The rents here are insane compared to other places.
This was 7 years ago. It was also on the top floor of a building with no elevator, so there were contributing factors to the $/foot. Everywhere I lived in Chicago got much more "bang for the buck" than Seattle though. Better summers and winters (I enjoy snow), and much better food as well. The difference in the homeless situation was shocking as well. The only thing Seattle has going for it, imo, is the nearby nature, but I honestly haven't taken advantage of it to warrant the cost of living increases on everything else.
You can still get $1500/mo for a 2br on the north side. Just be on the brown line instead of the blue line.
The trendy neighborhoods can be just as expensive as SF SOMA, but there's so much inventory, so the non-trendy but nice neighborhoods are much, much cheaper.
For a smaller place (900sqft for a 2 or 3 bedroom) they're asking $3200 in logan square.
Right arround the corner (western/armitage) they're asking $1800 for a studio.