Damn, dude. I'm also in Chicago. Nowhere near that level of success, though. Most first dates I've gone on in a week is 3. Scheduling gets way, way too hard beyond that. How old are you? How many months/years-long relationships have you been in? Are most of these internet dating, or people you meet through your social life? How long have you lived in Chicago
With internet dates, I tend to go only for ~hour long coffees, etc. I'm kind of a mellow guy, and there's often not a huge amount of chemistry; dates are nice, but kind of neutral. I'm also kind of new to the city, so I don't have anything resembling a regular repertoire of date ideas and locations in all of the possible neighborhoods I may end up.
Not everybody is cut out to dating that much with so many different people. I never thought I'd be able to get dates at that kind of rate, and it can actually kind of suck. It takes a whole lot of commitment to not only schedule the dates, but also keep up with the texting. When I try to schedule more than 2~3 first dates per week, I end up dropping the ball and do a poor job texting, leading to an increase in my fizzle rate.