...and would be more than happy to assist you in learning the ins and outs.

take a look.  The session you're looking for isn't listed, but I can cater a session to your needs, most definitely

The term that you are probably looking for is "mentor", not coach, depending on your needs.  I'm not sure what the big pansexual BDSM club is in Chicago, but they must have one.  Maybe Chicago Leather Club (CLC)?  Go to munches, network with other kinksters, join clubs, take classes.  Go on FetLife and seek out Groups specific to Chicago.

Failing that, since you are in the city that hosts the Leather Archives, you might poke around there to see if they have any suggestions for where to learn your craft.  If nothing else, a trip there will earn you some major street cred in the lifestyle community for knowing the recent history of BDSM in American culture (hint: it started with cheap military motorcycles being sold to ex-soldiers after WW II, and the beginning of bike club culture).

Yes, you can also pay just about any professional dominant to "coach you up" if you want to do all of this in private.  Most of them see couples, so you can just add the instructional element to your session.