(Marmalade's Badlands Guide hehehe)I've had an excellent time in Chicago but some of it is not for the faint hearted or those inexperienced at staying safe.
Chicago is divided into the nice respectable regions, including the city centre (which is a beautiful place to stay, especially overlooking the park and the lake) and many suburbs including the university area, and the 'no-go' areas of the outer suburbs. Most respectable Chicago white city dwellers have no knowledge of such places other than to avoid them and to feel shocked when scenes of them appear on TV screens.
Naturally, the best action at the best prices is in the no-go areas. As you head south, modern civilisation slowly disappears and is replaced by a sort of post-apocalyptic vista of concrete, buildings daubed with grafitti, disused factories and abondoned buildings and cars. It is rare to see white people in these areas. While all this recommends caution, it is not a black-vs-white issue (unless you are stupid) -- gang rivalries are between different black ethnic groups (eg certain African immigrants, of which there are several groups, and naturalised, born-in-the-U.S. Afro-Americans).
If you drive, you will ask security to keep an eye on your car (a tip might be an idea). Alternatively, find a literate, decent black taxi driver downtown and get him to take you there. It provides a sort of intro to the door staff who will then be more accepting (rather thna thinking you wandered down there cos you were lost).
The main entertainment is 'Gentlemen's Clubs' that are strip clubs with lap dances and usually blow jobs and sex in cubicles. You will get a lot more for you buck here than in any downtown U.S. strip bar (in fact they're quite cheap). If you are cool, you may get a free mini lapdance and grind from a girl as she walks round. When it comes to a private dance you need to negotiate hard and well (be aware of the local going rate -- ask one of the punters there if you are not sure -- and show you are not a foreign 'chump'. The payment for sex or blow job is called a 'tip.' If you can't get a taxi to pick you up afterwards to go home, ask the doorman.
Some of the clubs (a few may have changed or gione out of business, this is an old list I used) are
Polekatz Chicago Gentlemen's Club
Club 390
Arnie's Idle Hour (one of my favourites, but you will be searched for weapons before going in)
Club O
Industrial Strip
Atlantis Gentleman's Club
These are all to the south of the city and quite a decent drive. Negotiate taxi fares and factor that in (although the sex is cheap, the taxi costs add up if you go every night). There's one not so far and to the west of the city called Scores, but I've not visited it.
Find the by searching google, easy peasy. Check by phoning or with your cab driver to make sure they are still open.
This routine works for a large number of American cities, some better some worse.
There are other scenes of course... Escorts (often overpriced and very varied) and also massage parlours (known mostly in the U.S. as "AMPs" = Asian Massage Parlour). See rubmaps.com for info for the area you are visiting. (Note that not all AMPs offer extras).
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