We started hosting the Monday Jelly Chicago meetups this week and had a packed house. Next monday following Jelly some of the people here are starting a Startup Evanston meetup http://www.meetup.com/Startup-Evanston/ One of the members here also hosts the well-attended monthly Chicago Web Pros meetup in Evanston http://www.meetup.com/chicago-web-pros/
The startup I'm with is technically based in San Francisco, but I'm actively looking to find another developer in Chicago. If you are a Chicago-area Ruby developer, my email is in my profile.
I'm writing a book on design http://designforhackers.com
Based on blog posts at http://kadavy.net
I live in Lincoln Park at Clark & Fullerton, which I think is a perfect place for a one man startup. Very walkable.
I meet with other entrepreneurs every wednesday to cowork at a cafe http://jellychicago.com
I moved here from SF, entirely by my own volition. Yes, for real.
Launching a community for parent entrepreneurs called http://www.NaptimeEntrepreneurs.com at the beginning of May.
People, including 'pg, like to point out that "startups" scale and small businesses are structured to take steady income. But those lifestyle "small businesses" can flip a switch at any time and plow investments into any product idea to shoot for the hockey stick curve. They can even do it more than once.
To answer your question more objectively: we are ~4 years older and substantially larger than most of the companies discussed on HN as "startups". But our product team is roughly the same size as (I think) most of the YC'W11's.
The culture in Chicago seems totally different, would there even be a demand for that sort of thing?
noble tree is a coffee shop and chicago jelly meets there, but it is not a space where you can expect to go meet random hackers
pumpingstationone is nice but last i checked it didn't appear to have a strong technology startup type vibe.
i understand that curating the "vibe" of a "hackerspace" (whatever that means) isn't an easy thing to do, but i've been INCREDIBLY IMPRESSED by general assembly and hacker dojo. pumping station one is a great space, its just not quite the same. I'd consider:
nycresistor:generalassembly::pumpingstationone:"what i'm asking for" -- basically "general hacker types" (macguyver, picking locks and being generally crafty) vs "programmer hacker mindset" (hey, i wrote a really cool thing in node.js which i learned over the last 48 redbull fueled hours).
Chicago is an amazing town and there are tons of great people for it: birthplace of RoR, cofoudners of django live there, plenty of YC startups, groupon, beyond the pedway (woot, @timjahn, calling you out -- attended your "Entrepreneurs Unpluggd" event in Feb and I think that may be the best event I've attended in Chi), grubwhub, grubwithus, i think restaurant.com, etc.
However, the tech community isn't quite as unified and its a lot harder to get in touch with likeminded folk. At hacker dojo, you could turn to almost anyone to get feedback on a web app or ask for javascript advice, which I am not aware exists in Chicago.
That being said, in my eyes, things have come a long way in the past 2 years. Excited to see what the next 2 years bring.
Perhaps we need a meetup in Chicago that is similar to 106 Miles...
Every Wednesday from 12-4 we're there. Usually on the 3rd floor it seems.
Founded in 2009, raised a seed round in 2009, raising an A round right now, closing in May.
CEO - Dan Kuthy COO - Nick Yecke
Our inaugural event was Feb 8, next even is April 26, then late July after that. We really hope to create an evening for entrepreneurs to network, learn, and strengthen the ecosystem.
BTW, who is going to the hackathon, todady, http://www.nuhackathon.com/
Would love to get a meetup together soon.
inkling markets (first YC class i believe)
though i don't consider my company a startup, just a plain old small business.