You won't get actual users by having TC write about how "you're a cool website." That's not what you want. Why? Because there's no real value there. The real value is to be found in stories where The Windy Citizen's name is attached. Let me explain. If I was someone interested in Chicago news and was reading a blog post or an article in the newspaper and read "Windycitizen.com broke the story about the government scandal," I would either consciously or subconsciously realize that Windycitizen.com is something of value. They broke the story that I read. The traffic you'll get from this sort of marketing will be slower and more gradual, sure, but it'll be REAL traffic, not a traffic spike from TC because they said you were cool. Also, a site like Digg got its initial traffic because of Kevin Rose's celebrity. You don't have that, so don't look at Digg, if you are, as a metric since you two seem to be user generated social news sites.

As to actual marketing tactics, you need to create a story. Support a cause that stirs up lots of emotions. 'Support Protest Against Blah - Upvote!' Be known as the site that rallied individuals for a specific cause. If you can generate enough buzz about that, local blogs and even national outlets will write about you, not as a cool site, but as the site that helped facilitate a specific situation. Create a specific story.

Also, I'm not quite sure why you're after press from TC, or national/global press in general. It would seem that the traffic you'd get from them would be of no worth as someone like me in southern California wouldn't be at all interested in Chicago news.