Especially with respect to "getting it," that is, being respectful of the client's time, courteous and literate in responding, but also because of the massage and the overall experience I'd recommend:
1. David
http://www.masseurfinder.com/members/massagefixchi.shtml
Legit masseur with a wide repertoire of techniques, soft-spoken, articulate, mixes his own organic creams, does this as serious business and is kept pretty busy by regular clients. The sensual part comes at the end and includes some scented hot towels, which, as much as it is creative & nice, probably isn't a good match for those who like more "interactivity" throughout the session. I never negotiate this part upfront as I like things to be spontaneous and based on both parties being up for it, but am always pleasantly surprised by how smooth/enjoyable this part is and how gorgeous this man is. He does incalls in South Loop, close to the Roosevelt stop of the red line.
2. Jake
http://www.masseurfinder.com/members/musclejake1.shtml
He is more interactive and does outcalls. Super smart, engaging, fun and playful. He is also super-strong and can give you as much pressure as you like or can take, maybe not as educated as a masseur as David but the dude is smart and able to listen, so you get the pressure you desire. On a side note, I find it really frustrating that so many hair stylists give you the same haircut no matter what you tell them and similar goes for masseurs. Not here, and I also LOVE when he stretches me, I am 6'4" and 200 lbs. but the dude is so strong and lifts me like I am half the size :-).
Both are on the upper bound of pricing ($150-$160) for Chicago, but well worth it. While there are some decent guys who charge around $100, I invariably find them lacking in some respect, like being routinely late (even over an hour, wtf?!), having a weird hangup, not being into it, etc. So I have pretty much given up looking in this price range, but the worst is when such far-from-perfect guys, and there are MANY of those, think that they can charge $150-160, And then there are total basket cases for which you wonder why they even put an ad out there.
PS I saw this guy only once, he seems to have his act together and does an interesting combo of water/hot tub + regular massage. Super interactive but a little too young and wild for my taste so I never went back, but I suspect many here would enjoy:
http://www.masseurfinder.com/members/mikephelps.shtml
PPS My favorite masseur actually lives/works in Indy:
http://www.masseurfinder.com/members/luke462.shtml
OK, I won't say anything here, other than I absolutely adore him and his work and that by now it feels like visiting a close buddy :-)