I was looking to get into BDSM but I feel a bit lost with the whole scene.  
Wondering are there any teachers in Chicago looking to pass some knowledge  
I'm always approached with sessions, but I rather learn a bit more before stepping into a situation with my head cut off  

 
Even if it's a guy who has plenty of experience in the field ! I'm willing to learn haha

Fetlife has a number of forums for prodommes including help on getting started.

http://kinkykollege.com/
http://www.thecontinuumchicagoonline.com/continuing-education/
https://discoverycenter.cc/bondage-class-intro-to-domination-s-m

I also second FetLife as a source of additional info/local events.