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.
These are all good points. I never said I want TC coverage, just that I'm in a space where there is no TC, i.e. a relevant site that can send me lots of relevant traffic and that isn't afraid to link to me. People like to gripe about TC all the time, but it's done a lot of people a lot of good.
Your points about having a story are well-taken, too.
The reason why I'd like some coverage is because I spend my days calling up local businesses to talk about sponsoring us. None of them have heard of us. They don't care how many readers I have or don't have. If they haven't heard of me, it's not something they're interested in. Getting a write-up in the press would give me something to point to in that regard.
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.