For me it depends on circumstances that keep changing. It looks like this week I can get away one day after a morning meeting -- sometimes early Saturdays are good but I'm often not in town for a weekend rendezvous. I love business travel because I can arrange an outcall but unfortunately I haven't had the opportunity for that kind of travel for a while.
I would think it depends a lot on the hobbyist's employment and marital status.
Is it easier to get away on the weekdays, or do you find extra time on the weekend? I know in some cities girls do not work on weekends, this being the reason for my question.
I was also interested in getting more information on incall areas in Chicago. I was thinking in the Magnificent Mile area, but not sure about parking for guests.
thank you 
For me weekdays are easier to do. I work in the loop and can sign out of the office for two hours or so with out being missed.
Weekends have so many things scheduled that getting out is tough.
The weekday slots are most easy to find an excuse for absence.
However I've thought that with football season here that has a great window to play away from home that will not get scrutinized.
You will also discover that there are two audiences - those who can make downtown connections easily ( like comment above) or those where Ohare is so much more convenient. I'm the latter. Though I have made a few trips in. Yes, parking is a problem.
Thank you both for your input. Its nice to have opposing views! I'm not sure what the loop is, but I'm definitely going to find out because I've seen mentionings of the area on a few posts during my pre-post research.
Thanks guys!
Xoxo,
Allison 48J
The loop is the central city business district. It gets it's nickname from the elevated subway tracks that form a "loop" around part of the business district.
In reality it is the area bounded by the lake on the east, the Eisenhower/Congress expressway on the south, the Chicago river on the west and north side. Some would extend it out a bit more.
Thanks guys!
Xoxo,
Allison 48J
Cool. I actually found a few hotels in that area I am interested in. Finalizing and booking before I close my eyes tonight. Thanks hun!
Xoxo,
Allison 48J
Finding parking downtown is easy; you just have to be willing to pay for it. Hopefully, it won't cost more than your date.
For me it depends on circumstances that keep changing. It looks like this week I can get away one day after a morning meeting -- sometimes early Saturdays are good but I'm often not in town for a weekend rendezvous. I love business travel because I can arrange an outcall but unfortunately I haven't had the opportunity for that kind of travel for a while.
I would think it depends a lot on the hobbyist's employment and marital status.
Great point! Although your response makes me want to ask another question ... that I am not touching with a hundred foot pole! I think I may be a bit too new here for that, and I have seen the way some guys can get on these boards. Thank you for your insight. I can sometimes forget the work you guys have to put into discretely scheduling your appointments, so I try to be as accommodating as possible.
It's nice to see your attitude of respect. It 's very attractive to me. You can PM me if you have another question and I should be able to retrieve your message in a few days after I've had some play time and got my VIP status back 
Well thank you. A little respect goes a long way, especially in our little taboo world! I don't have VIP myself, for some reason my card doesn't work with this site. Are you a p411 member?
I've always stayed downtown and I stay on State Street not too far from the Mile. This trip I've decided to stay for a few days in Schaumberg too as I know it's not easy getting around this great city!!