There is a few girls I've been looking @ but havent pulled the trigger to make contact yet:
Penelope, Samantha, KitanaRose, Sissi and TS Desirre are the ones I've narrowed it down to. Can you help me squeeze the list further? I'm interested in topping first and then if the mood is right, getting topped. I've been with a few different female providers here in Chicago and also in Vegas and have always wanted a girl with "a lil somethin different." I've read all the reviews on them (that I could find anyways) and I want to take the next step. I considered hitting ElGato Negro but I do not wish this part of my life to "go public" and perhaps get back to my SO. Thanks for any help or advice you can give!

Just book an appointment with one of them.  She will take it from there.  Enjoy.

Why go to a bar and take a chance?  Just hire one of the pretty ladies from your list and you will have a sure thing and be happy.

Most definitely Penelope, by far the best of the girls you listed.

Quite a bevy of beef up there in Chicago Eros! KitanaRose gets my vote. However, Maizza is one of my ATF. Check out her reviews before you scratch this S.A. hottie off your list!

I've seen Kitana (very hot looking, mostly a bottom I think, not a kisser), Sissi (hot, goes both ways, fun, good for a first timer) and Desirre (hot hot hot - only a bottom with me, very feminine and was my first).  I think Desirre may be out of town so I would try Sissi.  I think Alexa is great as well.  When you really want to get topped - go with Eva or Alexa!

Good luck and enjoy.