Well, I'm subscribed to a few podcast and they generally have web sites to go along with them, but I almost never go to their sites, eve when they ask me to in the podcast. And honestly there isn't much they could do to make me more interested. I don't have a ton of spare time so I need a real reason to visit a site.
That's the key. Why should people be visiting the site? Try to get an understanding of what people are looking for when they come to your site. This can be achieved by using site statistics software, which can tell you what search terms a person used to arrive at your site, and also you can setup a survey for visitors to fill out. This'll give you a better feel for what people want, are looking for, and maybe what will keep them coming back.
As can be expected a site needs dynamic content for people to have a reason to come back (except for reference type information). You seem to have some of that going on with the podcast, but if they're subscribed, they don't have to visit the site to get that podcast. (I'm not suggesting forcing people to visit the site to acquire the podcast. That would definitely backfire.)
Another point I'll make is advertise. Find ways to get the message out that the site exist. Only people in Chicago or going to be visiting Chicago will care about the site, and that works against you since you have less people to take interest (in comparison to a more globally relevant type of site).
Looking at the code. You use Chicago repeatedly in your keyword list. Once is all it takes and using it more times can be penalized by some search engines, believing you are using "corrupt" tactics.
Design-wise I would rework the left and right hand sides at least color-wise. It feels very boxy and cramped. On pages like Bars and Restaurants supply a list of those being talked about on the page at the top to act as a navigation. It's hard to tell how many Bars or restaurants are listed on the page without scrolling the whole page. People may think you only talk about the first one listed and never make it down the page.
You seem to have a lot of good information on the site. I'd still try to add more details to areas to give it more text. This'll help search engines pick up more information about the site and increase the chances of your site showing up higher in a search result. Just don't over do it with too much information since people also don't like to read too much.
OK, I'll shut up now. Hopefully something here can help you. This is a very complex area and entire books have been written on the subject.
