I recently made the decision to begin freelancing, so I put together some profiles on oDesk, Elance, etc and started looking for clients. I was relatively lucky to land a client a few days after starting to look at a reasonable rate (was a fixed price, at the end of the project >$20/hr)editing a premium one page WordPress theme for a small business in Australia. I then made some simple web advertisements and a simple personal page for a friend of mine.
After finishing that first project (a bit later than I wanted, but the client was happy), I went back to those same sites to continue my search for clients. After researching on my own and spending time on these types of websites, I quickly realized that I was not going to get a steady flow of work at reasonable rates. I turned my attention to friends and acquaintances who either owned businesses or need things done that they didn't have time for themselves; those resources were quickly exhausted.
Currently, I have a very minimal portfolio hosted at http://kylechalmers.me, this is the second iteration and was my minimum viable product.
I am getting my clients (very) slowly through freelancing sites. I have started to make business to business calls to local businesses who either have a poor web presence, or none at all, however, as expected, I am not getting many clients through this method.
I've ordered a stack of business cards to leave around at local bulletin boards (grocery stores, restaurants, etc), and have begun to think about going to small business meetups and similar events to start networking.
My question is, as a freelancer looking to expand my business with the intent of moving into more technical projects later on, how do I go about most effectively growing my business and network? And more specifically, how do I start getting a steady flow of client coming to me, rather than me searching them out (which I still expect to have to do, at this point atleast)?
Avoid passive, low-value channels like putting cards on bulletin boards. You need to go into an active sales process for securing high-value clients.
Looking at your site, I'm thinking the kind of clients you're going after probably don't care about the technologies you use. Instead, organize the content more around the business problems that you solve for your clients.
See if you can find a particular type of business/client is undeserved. Get one of them as a client, and write up a good case study or white paper. Then book appointments with as many of those types of businesses as you can, tell them the story of how you helped the first client, and how you can do the same for them. If they don't sign up with you on the first meeting, follow up consistently.
With an approach like this, you're coming in as an expert and you have much more altitude in the transaction than if you're being hired as a "Wordpress theme integrator" or somesuch.
You're in Chicago, you're not going to run out of leads. You need to start booking as many sales appointments as you possibly can. Put a lot of practice into how you tell your story. Practice answering common questions. Video yourself doing this, review including your voice, tempo, etc. Consider getting sales and/or speaking coaching.
Call design and communications agencies in your area to let them know you're available. Some agencies often bring in freelancers to supplement their teams when demand is high. (For these folks, your technology lists might be slightly more interesting.)
Invest continuously in building your own network, including people who are not your potential clients. Make sure they understand what you do well enough to recommend you within their network when appropriate. Consider offering a referral percentage to people with good networks who refer clients to you.