"Lobbyist Online" is a website set up by Cook County Clerk David Orr to track the lobbying that goes on in county government. It's a handy site. You can easily browse and search a list of all the firms and individuals registered to lobby county public officials and staffers. Conversely, you can click through a run-down of elected officials and top county staffers to see who they've been talking to. There's even a way to get a sense of what officials and lobbyists are discussing. Check out, for example, what comes up when you select "Contracts and Bonds" under the "What Are They Lobbying About?" section for all of 2010. That's a long list of meetings, phone calls, and emails about excess insurance coverage, health care contracts, red light cameras, bond ratings, "deal closing" with Morgan Stanley, and much more.
The City of Chicago requires less information from lobbying firms and individuals. A PDF file (the latest one is here) shows who is registered as a lobbyist, who employs them, and who their clients are. You don't get to see which elected officials and city staff they've been chatting with, and what those conversations have covered.
The mayoral challengers in Chicago have made lost of noise about bringing transparency to city government during the current campaign. They'd do well to look to Orr's office for ways to shine more sunlight on City Hall lobbyists.