Chicago's traffic (plus possible snow now that we're into Winter...Brrr) means that if you stay in the burbs the majority of your business is going to come from clients staying there, and vice versa if you are in the City (Loop/Downtown), due to the exorbitant amount of time it takes to get across town. Downtown can be congested and parking is not cheap, but many providers like the City for the excitement and hustle and bustle. You are steps from the best restaurants and nightlife which is great for extended/overnight dates.
During the weekends, upscale hotels are filled with women dressed to the Nines so if you like dressing up and meeting your clients at the bar, you'll blend right in and no one will be the wiser (unless you're too obvious). Suburban hotels are more casual and things are more spread out. This is purely based on my own opinion. For me, I live in the City and hardly ever venture out into the 'burbs.
No matter what, people will complain no matter where you are or what you do. And others will praise.
Many people from the burbs don't go to the city,and many people from the city don't go to the burbs. But there are people in both places. I've done well in all areas out here. Loop, not so much unless it was for outcalls. Tons of outcalls in the Loop. There are some areas in the burbs that have lower hotel rates, free parking, and great clients (very convenient off the highway). Just be ready to go into the city for outcalls if you choose the burbs. Guys are pretty understanding of travel fees for you to come to them.
It turns the whole trip around. So you have your early evening 7-8pm booking, then turn the phone back on! Stay in a nice place with a cool lounge scene and get them to hop a cab and come to you. Stay btw the Loop Mag Mile and the Gold Coast-and use RS2K. They are golden. Good luck!
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