1. Can I get away with not advertising on RoomService? I was thinking of a "Verification Only" account.  Yeah you can get away with it, but a LOT of people use room service here and I think it will more than pay for itself.  I would recommend it.

2. I am constantly told to come to Oakbrook. Your thoughts? Anything I should know about Oakbrook? LE, areas not to stay in, etc.
Oakbrook is a good locatioin.  Lots of restaurants, shopping, and business locations in the area.  Just be sure to properly screen and not advertise on backpage.

3. Downtown - My usually haunt, but it's been awhile. Any activity or hotel info that might be relevant?
I have used several different hotels downtown but of course its just parking is a bitch!  lol..

4. How important is outcall? I was thinking of a rental car for the possibility of outcall, but to be honest since I am not from Chicago and don't know the area that well, outcall kind of not high on my list.
This just depends on a few things.  Like if you stay downtown, then I would not worry about it.  It may be more of a headache than its worth because at the hotels you have to pay for parking daily.  And sometimes everytime you leave and re-enter you have to pay again for parking.  So it may not be worth it.

If you stay in Oakbrook or any other area and you want to do some site seeing too, then rent a car.  You can always mapquest directions and stuff so just because you do not know your way around dont let that stop you.  Just depends on what you want to do.  If you would only rent a car to do outcalls, then I probably would not rent a car.

I hope that helps you girl but I am sure others will have some answers or suggestions too.  Either way if you are coming, have fun here and be safe.