Sirnanigans, you are in Chicago. There is a large contingent of straight razor shavers in the busy metropolis of my former home. Go to the link below and scroll down to Illinois. There you will find TwistedOak listed as a honing/help resource. You only joined this month and have a long, enjoyable road ahead of you. Read the Library, or at least the FAQs. A lot to be garnered there. Start your trip with a properly honed razor, you won't regret it.
Local Help - Straight Razor Place Library
There are a few meets here and there in Chicago, take advantage of them and meet fellow shavers. For all you know, there may be one living right next door to you.