Many of the the gents closer to downtown will say downtown.

Many of the the gents closer to the burbs will say the burbs.

I am not a fan of parking my car on the street, but I must say the parking meter deal our previous mayor entered into opened up spaces for the quick hit and run in general.  But your point is taken about parking if you are downtown longer than that. I also don't care for the congestion.

As far as the burbs, a little more spread out and in general the parking is free.  Oakbrook and Lombard are my favorites.

This is the first time I've stayed at O'Hare and offered OutCall to the burbs, and it's a whole different ballgame.  After 4-5 No shows and last minute cancellations last week Downtown, I find the burbs more relaxing and the guys more reliable.  Not that I don't love Downtown Chicago, but the extreme costs and the hectic pace (hence the unreliablity) made for bad business.
My 2 cents!

Clair

I have to admit that I come from the burbs, but getting downtown is just a pain. Traffic, parking, etc. I would much rather visit in Lombard, Oakbrook, O'Hare (though disk like always having to pay for parking at O'Hare).

.......see girls downtown.  if i still worked down there, that would be my playground.  but i am in the burbs and will never head downtown for a lady.  traffic hassles and parking are too much.

from your safety standpoint, the city is crazy anal to bust girls.  has been for at least ten years.  chgo leo puts manpower into calling and setting up girls to bust.  they want to keep the nice mich ave hotels safe for us civilians i guess.

ohare and schaumburg are pretty safe.  very rarely do the suburban cops waste their time.  only exception is if the woman is stupid and running a turnstlye at the hall door or if by random chance the county if running a mass sting, which only happens once a year or so.  when that does go down it seems they are picking ont he bp or cl advert.

good luck

randolph

I think Randolph1 and ChiAndrea's postings are worth reading.  I live downtown and have ventured out to the NW suburbs on occasion, but only in search of something seemingly unavailable elsewhere.  I travel by public transportation.

It's worth keeping in mind, as the other writers have implied, that not all suburban locations are equal in terms of safety.  The majority of law enforcement situations one reads about seem to occur out in Naperville, and you never read anything about the O'Hare / Rosemont / Schaumburg areas.

As for downtown Chicago hotels, I'm unaware of any problems there.  My hunch is that they're simply too big and busy to be bothered with the occasional lady who enjoys entertaining gentlemen.  Obviously, a little discretion never hurts, no matter where.  Issues like parking are only going to matter with people who travel long distances to visit and who are unaware of the many downtown options.

I wouldn't want the hassle of having to get into a car and having to drive to the burbs.  On a nice summer/fall/spring day, there's something lovely about approaching the destination on foot, and there's something nice about just hopping on the EL afterwards and dealing with that blissed-out feeling without having to be in charge of a motor vehicle.

Welcome Betty B,
I have ladies in several locales, D.T., near north, Gold coast, LP, Lakeview , oak brook, Lombard, Rosemont, AH, Schaumburg, and on..
Many visiting Ladies split time between botique and 4-5 star hotels in DT a few days, then Oak Brook, or Schaumburg for a few more days,  they get to see their clientele in both areas.
Personally traveling is Chicago is a pain, but one gets used to it.  
As a tradesman, I work the entire city.
I live in the near west suburbs so I'm well centered.  Be Flexible, have Fun, and enjoy everything the entire city has to offer.

...downtown or suburbs, via major roadways. Discreet, clean, AND there is always free street parking

If you live and/or work near downtown Chicago, you prefer to see providers in downtown Chicago. One truth about Chicago area traffic is that after 3:30 pm on a weekday, if you are trying to get anywhere via an expressway, you're in for rough time. By 5:30, a trip from downtown to O'Hare, Oak Brook, Naperville  or any northwestern suburb would be at least one hour of creeping along at less than 20 miles per hour.

The flip side of that is a large number of people live and/or work in the suburbs

I live and work in the city.  If a girl is in the burbs she's not even a consideration, I simply won't bother.

So this is just another way of saying what everyone else is saying.  City guys likely won't go to the burbs, and burbs guys won't come downtown.

Search the board too, this topic has been debated a thousand times over.  The only way to cater to both audiences is to split your time between DT and a burbs location.

Thank you for all the opinions/comments!