Downtown is a pain because of traffic, parking.  Stick with the suburbs.

I try to avoid downtown because of no or limited parking available.

Personally, I don't go downtown.  I'm happy with O'Hare/Naperville/Schaumburg/Downers (popular spots surrounding Chi).  Naperville is probably my favorite.

Too much LE watch. Unless you're staying at an upscale hotel and can get around the issue of people at the front desk keeping an eye out.

Which is why downtown is better.  Or Oakbrook.

Gents who would have to travel the Ike (290) will not come to Oakbrook/Lombard.  Those on the North Side would use the Kennedy (90) to the Tri-State (294).

when you are happy, the chances that we are happy is higher.

You will find potential clients either downtown or in any of the sites mentioned. If you are actually taking an unscientific poll, I prefer Oak Brook and parts west along I-88. I will go downtown if the urge is great or I happen to be spending the night. I'm from out of town 150 miles west and regularly drive in and out on a day trip.

While downtown is difficult for burb dwellers, it can be a greater strain for some downtowners to get out to the burbs.

You will find it more difficult to get around in the burbs without renting a car. It’s easier to get a cab around O’Hare than other places, but still not as easy as the city, unless it’s raining of course.

You can usually find hotel deals unless it’s a major event week/weekend, but burb hotels are a little cheaper and many are just as nice as downtown. Your dining choices will be greater downtown, but there are still many nice places elsewhere. I suggest you spend a couple of days downtown and then move further out for a period. You’ll end up with a shorter trip to the airport home and you will have a chance to make EVERYONE happy


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I prefer the suburbs, Oak Brook, Schaumburg, and O'Hare are some of the places I have met ladies. With I-290 being under repair, it will be more difficult to get downtown, so I will probably stay out in the suburbs for my hobbying.

Downtown without a doubt.

If a girl is staying anywhere except downtown, it means zero chance that I'll patronize her services.

Just search the Chicago board, this question has been asked and answered a thousand times over.

No matter where you stay you will make some people happy and will eliminate others from possibly seeing you.  The city guys won't trek to the suburbs and vice versa.

The best answer is to divide your stay and spend half of it downtown and the other half in the burbs.