Welcome to SRP!

As already mentioned, no need to fear a used razor. More often than not they are of superior quality (grade of steel anyway) than modern razors--with the exceptions of the Dovo's and Bokers being produced currently which I have read good things about here on SRP (though I have no first hand experience). A quick application of a disinfectant such as alcohol will make double sure the blade is sterile.

The vendors mentioned so far are great, but I'd add whippeddog.com into the mix as another vendor who sells razors that are honed; specifically so that new straight users get a good first experience, and they're about the cheapest razors you'll find outside of the classifieds here.

So far as users in Chicago. There is a member map you can check out if you click on "Community" in the bar at the top of the page. There's also a members list that you can search for Chicago/Illinois. However, you'll only get results for guys that have filled in their location in their User Control Panel/Profile. The Member Map also only shows those members who have taken the time to place their marker.

Best of luck on your journey into straight razor shaving!