I actually had a hard time(it's normal) starting in Chicago. Just ask the guys in the Chicago thread in Hook up...
Previous to Chicago, I was a prop. trader in Los Angeles, trading using discretion, for about 7 years. I taught myself to program in Tradestation and WealthLab to get into system trading because my goal was to become a hedge fund manager.
I moved to Chicago to work for a hedge fund so that I can learn and build my skills as a trading system developer. But I couldn't get a job initially due to my educational background, 2 years of college, which I dropped out of to start trading. So for 3 years, I paid my bills as a chef in a restaurant, which I became fairly good at.
During that time, I built my experience, skills, resume and most importantly networks. I was working small projects for little to no pay, developing systems and programming different applications for trading. Obviously, I had to teach myself to program in C++ (C#) and learn about technical order dynamics, computer networks, quantitative math, and whole lotta other stuff.
Seriously, it wasn't easy being where I'm at. I'm in Sydney, Australia right now working on a project from a Chicago trader's recommendation. Then I'm going to Japan, for another position. I had to go through 3 years of shit, even when I was a profitable trader and a better developer than most of the guys out there.
Especially in Chicago, 1/2 of your success comes from who you know. And of course, the other 1/2 being what you can do. Networks can get you inside the door fast. But you need skills to stay inside and trust me, firms cut people fast, unless you're cousins with the owner or know someone large....
My recommendation is:
1. Be really friendly but also very business. Work hard on building relations. Even if you suck, if the people in the firm likes you they will keep you around and "try" to teach you to be profitable.
2. Be smart. You have to show the firm, the potential of becoming profitable. They'll give you a few chances here and there.
3. Work hard. Even if you befriend everyone, I'll give the guy... 2-3 months to breakeven. (2 weeks for a regular Joe to be fired)
4. Learn a lot about sports like Football, Baseball and Basketball(Pro and college). Out of trading, this is all they talk about. (ahhh... also woman, sex, drugs, nightlife stuff) It's good to have a good knowledge on these to break some of the ice, with other traders....
Good luck...