I don't have much input on the burbs but I've been in the city always in an area within ten mins of the Loop and easy street parking.  The area has enough people that anyone coming and going blends in easy as I don't want to draw any attention to myself or clients.   There's also a good amount of providers who have in calls  in the burbs for a long time, I'd guess this has worked out well for them too.  I think the consistency is key, my gentleman always know where I am so if they have a cancellation in their schedule it's relatively easy to book with me if we've seen each other.  
My best advice is just start checking out places get a feel for what's comfortable to you.  There's no shortage of men in the hobby in the burbs or the city.

Good luck,
Alyssa

Working strategy, maybe

I live in the city and don't have a set incall yet. So I'm thinking about being in the suburbs for a couple days each week and in the city the others but ugh. It's so much to think about. Lol

Chicagoland can be kind of broken up into two main areas. Most men from the north and west of diverse and Ashland won't come into the city, and those that are within that area won't go out. Best is to have a more stable incall in the city, and just hotel it in the burbs.

I agree, it's about the same - I've noticed it's most effective to pick a place and stick around a while.

For me, it took about three months for things to "click" that I was in the west burbs/Oak Brook etc etc etc... but once it did, I was able to add locations and spread out after a year. So I'll go downtown or Oak Brook-ish upon request. (That was difficult - I had to make it a little more clear that I book incall based on request, I do not sit at my incall.)

I'm learning location has more to do with convenience in knowing they're going to know where to find you the next time if they like you.

I'm learning, clients tend to need to scope out the areas they can fuck in without running into the wife, husband, boss, secretary, (unless they pre-arrange that).

So a lot is planned ahead.

Probably way TMI, but there are clients everywhere... I imagine some have their "locations" planned out to fit in with their lives without cross contaminating...

xoxo

Good luck!

Honestly, I get around a bit, so I'm fine with seeing providers both in the city and the suburbs, as well as a bit beyond into Milwaukee, Rockford, Madison, down state, and sometimes North-West Indiana and even beyond on occasion.

My own thoughts? The city seems more central and tends to have better options. Parking can be a bitch. I prefer to drive rather than take public transport so that's just me. The suburbs... well it can be a bit more conspicuous. I honestly don't mind if people think I'm going some place to have sex with a woman, in fact, it's kind of hot knowing that people know I'm having sex with someone. But, as a provider it probably puts you at higher risk from uncle LEO. The city offers anonymity.

I'd also point out that most people in the city itself aren't likely to travel to the suburbs, while most suburbanites (or at least the ones you are likely targeting) can at least commute to the city. Sure, some suburban types never go into Chicago proper, but those same people don't strike me as the type to visit a provider anyway so forget about them.

As a business man that travels weekly, I prefer the burbs. Going into the city is a pain in the axx. Traffic, parking and finding your way around is way too time consuming. The Schaumburg area is closer to the interstate and easy to navigate and parking is much easier.
Besides the Hotel Sofitel is about the only place ladies stay. You can go into the lounge on any given night and find MANY providers checking out the scene. If it's the easy for me to detect, how about the employees?
Anyway, just my opinion, but the burbs are less stressful. Rates don't matter much, but paying an additional $50 just to park downtown isn't worth it to me.

It's much easier for those of us who live outside the Chicago area.

Parking is a nightmare in the City, and ridiculously expensive. If that were it, I wouldn't be swayed, but the traffic to get to the city is ridiculous as well, it could be 40 minutes or 2 hours.

All things considered, the aggravation of getting downtown, I'll gladly book with a lady in the burbs before I'll book with a lady DT. I'm not a downtown kind of guy though, so I'm way more comfortable in the burbs.

My $.02 worth.