Prostitution, Prostitutes, Escorts, World Sex Guide

Chicago Page 1

6/1/01 --- Chicago Streets Update

Well folks, it's been a few years since I sent you an update. This was due to the demise of the site. (it was up, but no one maintained it.) Now that Action Jackson ( is running the site, I'll be sending you regular updates from my travels.

Well, Mayor Richard Daley's plan to become the pope is one track. He has successfully closed down several strip clups, and put strangle holds on those that are still open. The girls at the Crazy Horse Too can't even touch you casually - I mean they can't even touch their leg to your leg when doing a "private dance".

If you are looking for awesome gentlemen's clubs, go to Las Vegas, Dallas or Tampa. Stay away from Chicago!

As for Chicago street walking - it's WAY down from the glory days. Over the past few years, I've seen maybe 20 different hookers - total. You keep seeing the old ones over and over again. The crack head aids carrying hookers...

I stopped doing the whole cruise up to Lincoln and Jersey (by the Stars motel). I haven't seen anything up there in years, and although I occasionally hear of someone seeing a girl up there, it's not worth the 30 minutes drive up there from downtown Chicago.

I also gave up on Cicero avenue, although I know there are girls still there. They don't hang out much on the cicero side anymore, your best bet is to look north of the Eisenhower (290) on Cicero avenue. The area is totally black - so if you see a white girl she is probably a hooker. (YEAH YEAH YEAH, DON'T SEND ME STUPID EMAILS ABOUT RACISM AND GENERALIZATION. STEREOTYPES EXIST FOR A REASON, AND WHAT I SAID WAS NOT RACIST. It's only an observation from my own personal experience.)

Armitage still has a few girls, but way ugly.

North Avenue (& Wabansia) is mostly dead, but occasionally you can find some fresh young talent. These girls come into town hearing that "North Avenue is the place to make money." The cops have been really beating on them hard, especially in Wicker Park / Bucktown. The area is undergoing a gentriciation, and the residents call the cops the minute they spot a girl. After the girls get arrested a few times, they usually flee to kinder terroritory.

Occasionally you will see a girl (black girl usually) in front of the home depot and few and far between you will see a girl as far east as Halsted and North.

More to come later...


Date: 21 Sep 1994

The most obvious area is on West Madison around the site of the Stadium (and the new United Center). Unfortunately, the reason they're so obvious is that they're so desperate. This is one of the most depressed areas in the city, and you can sometimes hear gunshots if you're still on Madison west of Western avenue (in Chicago, North Avenue runs east/west, and Western Avenue runs north/south).

Not only would I NEVER consider giving these ladies any business, I wouldn't even want to shake hands without wearing surgical gloves. Even if you didn't contract AIDS, you'd stand a good chance of pleurisy or hepatitis, I'd think.

For people in this area of Chicago, its awfully hard to make it through life.

Date: Wed, 24 Aug 94

North ave between the xway and clybourn after 10pm. I wouldn't touch any of them with a 10 foot pole (or my pole).

Date: Thu, 4 May 1995

Wanted to share with the readers where I've seen streetwalker action in Chicago. If you take it for granted that scuzzy women that walk up and down the street looking into cars and waving for them to stop are hookers, then you will have good luck in Chicago.

Most of the directions can be found on a good map of Chicago. Some of these places are in bad 'hoods, so be careful. Try to take a major highway or street to the general area.

Blowjobs are $20, and a half & half (blowjob/fuck) is not much more. You should probably insist that they use a condom, even for head. Try to find them in groups. An undercover cop is pretty unpopular with the professionals. Also, news reports indicate that cops will impound your car if they catch you picking up a hooker, even if she isn't a undercover cop. This could cost over $400!

Either pick em up quick with you car, or better yet, park the car a block or two away someplace safe (ha!) and walk right by 'em. Make significant eye contact and they will follow you around the corner for a discussion. If a cop sees you, you can always say you were walking along, minding you own business when this hooker started bothering you. This scam is less effective if you are caught with your dick in her mouth.

Areas of Prostitution Noted

Where: Vicinity of Armitage and Campbell, about 1 block west of the intersection of Armitage and Western. When: 9 pm - 11 pm and beyond. What: Bedraggled Hispanic, Black, and White drug addicts. Hints: They are usually standing on the south side of the Armitage any where from Milwaukee Ave. to the east to California Ave. to the west. If you don't see anything, go around the block clockwise starting at Armitage and Campbell. Sometimes they are hiding around back. I've only seen two that looked attractive, but I don't get very close. Last Noted: April 1995.

Where: Vicinity of North and Elston, about 2 blocks east of the Kennedy Expressway, North Avenue exit. When: After 11 pm. What: Mostly black women in classic hooker garb. Hints: They are usually standing on the north side of North Avenue anywhere from the Chicago River Bridge to the east to the Elston Avenue in the west. They sometimes congregate near a used office furniture store. On weekend nights you might even see a gay guy hustler (who isn't dressed up like a woman). Last Noted: April 1995

Where: North Avenue, west of Ashland and east of Damen, on the north side of the street. When: After 10pm. What: Mixed bag, both in looks and clothes. I once even saw a cute white woman, but she may have been a Wicker Park resident going home from a late night out. But why was she waving at me?!? Hints: They are well scattered along this long stretch. But they seem to be the same women all the time, so it's likely that they are genuine (not cops). Last Noted: April 1995.

Where: Armitage, east of Pulaski and west of Lawndale. When: Very rare, but almost any time. What: Tired white women looking kinda dirty. Hints: There's a bench at the corner of Armitage and Springfield where this one woman hangs around. It looks like a woman at a bus stop, except there's no bus stop there. Also she's giving every car the once over. I've also seen other people in that area, but none which look obviously like a hooker. Last Noted: January 1995.

Where: Cicero Avenue, south of Belmont Avenue, on the west side of the street. When: Believe it or not, around rush hour! What: Bedraggled-looking white chicks, probably goofed up on gop. Hints: If there's a druggy looking white chick looking around nervous-like and smiling and waving at you, that's a hooker. Last Noted: April 1995.

Where: Cicero Avenue, north of Cermak (22nd Street) in Cicero, just north of the Subway tracks. This is in Cicero, a suburb west of Chicago. When: Most evenings. What: Drug-addicted hispanic and white women. Hints: There are two bars and a hotel on Cicero Avenue that basically allow prostitutes to hang around: The Cove Hotel, the adjacent Cypress Lounge, and a package store about a block north and across the street. If they aren't on the streets, drop into one of the bars. When a woman drops by, even if she's with a 'boyfriend', start up a conversation. The words you need to hear are "Are you dating?" There are only two types of female attendees to the Cypress Lounge, the old alky regulars, and the working girls. Last Noted: May 1995.

That's all for now. Feel free to add you own comments, new places.

Subject: Filling in a few gaps in the large posting about Chicago Date: Wed, 24 May 1995 15:39:36 UTC

The last post you have about Chicago is pretty impressive. There are a few gaps.

Where: Diversey, Clybourn between Leavitt and Damen (Lathrop Homes)

Types: White and Black drug addicts. Mostly coke fiends. They are proud of the fact that they don't shoot up.

When: Whenever there are people around. Between 6:00 PM and 6:00 AM.

Note: Most of these women are pretty scary looking. They also will be agreeable to whatever you want to do. Be careful, when people talk about high-risk groups, these are them.

Where: Wilson Ave. Between Clark and Broadway.

Types: All types. Mostly drug users or alcoholics. Some look young, but not when they get up close.

Most of the women are black, Native American Indians, or hispanic. There are on occasion whites, but usually not until their checks run out.

When: This is interesting. The neighborhood is changing, so it is harder to find them early in the evening. Later is better. So about 3:00 AM, you might see a lot out there.

Also, some of the more brave are out in the early morning. If you see someone that doesn't look like a jogger at 5:00 AM - 7:00 AM, see if they will make eye contact.

Note: The neighborhood is changing. There are a lot more cops on patrol than there used to be. I've never seen an undercover cop pose as a prostitute, but I've seen plenty of guys pulled over by plainclothesmen. Cars impounded, the whole shot.

Where: North Ave. between Damen Ave and Elston Ave.

Types: Blacks and Hispanics (light and dark skinned) There have been some white girls, but they are few and far between.

When: During the week (Monday - Thursday) After 11:30. During the weekend. 6:00 PM - 8:00 PM or early in the morning.

Note: The neighborhood is changing. This brings more police around, but generally speaking, they only pick up the white girls and leave the black girls alone.

There are several bars with 4:00 and 5:00 licenses. Because of this, there are a lot of young people milling around Damen, North and Milwaukee most of Thursday, Friday and Saturday nights. For this reason, no prostitutes are around after 10 during the weekends. Of course, there are a few die-hards, but they are very scary looking, and they are unquestionably pros.

If you see anyone passable, and white during the weekend evening and nighttime hours, she just came out of the bars. The cops have been known to bust guys who drive slowly down North Ave if they honk their horns at anyone. I've noticed that if they are from the suburbs, they don't impound the cars, but they do take them in for the night, and if they are from the city, they let you go, but take your car.

Subject: Chicago street action (circa 1/96) Date: 16 Jan 1996 22:39:24 GMT

Well, the group is over-due for an update, so here's the results of a few recent cruises I've taken on the streets of Chi-town.

North Avenue, Kennedy Xpy to Milwaukee: Dead, nobody out at all.

Armitage, Milwaukee to Cicero: A couple of really un-attractive black girls that had 'junkie' written all over them cruising from Central Park on east. Not standing or doing anything flashy, and they kept moving, so I expect the heat is on in the hood there. (Probably the ONLY heat in that 'hood <G>)

Saw a girl twice, standing in a doorway just east of Cicero on Armitage (north side of street), young hispanic, reasonably cute...but each time I came around for another look, she was gone and what appeared to be the SAME 2 uniformed cops were rousting a guy in a car 1 block north (near auto dealerships)!!!

Looks like some of the entrepenour-ship that the city of Big Shoulders is famous for, folks....AVOID! (unless buying off cops is your idea of a good time)

Cicero Avenue, North Av to Archer: Very little happening the times I went through the black area (North to Roosevelt), may have been the weather, usually not a great area anyway (unless you're LOOKING for black junkies who will gladly rob you)

The Cicero strip (Roosevelt to Cermak) is DEADSVILLE! Too much recent heat, although you will occasionally find something really used looking hanging just west of Cicero Av on 14th street. 14th street is hard-core junkies and LOADS of gang-bangers (if you don't catch a disease, you may catch a bullet) NOT RECOMMENDED

Some recent action near the corner of 31st and Cicero, mostly older girls, but experienced and good value, if not much to look at. Cheap and sleazy motels (4 of them) are close at hand. Had bad times in that hood about a year ago, when some chick was posing as a hooker, and when picked up and parked, her boyfriends came in pointing guns and robbed a few guys. Don't think the coppers caught 'em, but they seem to have moved on, anyway. Neighborhood is now getting very gang-y, RECOMMENDED, but use caution.

The area around Archer Av. is getting good again!!! Around 4am saw several fairly cute, white girls out. HIGHLY RECOMMENDED, but be wary of the coppers, it's only a moderately busy district, and they may find time for YOU.

Met up with a girl who called herself 'Suzie', but when I asked for a number later, wrote down 'Julie' (and when I dated her last, she called herself 'candy'). Polite, careful, and gives a good blow-job for 20. Last time I ran into her, she said she only does blow-jobs, didn't ask this time (just enjoyed her company <G>) Will CERTAINLY repeat with her!!! HIGHLY RECOMMENDED.

In other news: Judging from the recent ads in the sports section of the Chicago Sun-times, the massage parlors are changing hands again. Moving and changing their names/owners of record. This usually means the heat is on <sigh> and the girls will be cagy, unless they know you. Can't be 100% sure about that last prediction, as I don't patronize the massage parlors anymore (reversal of fortune <G>).

Date: 20 Jan 1996

North Avenue, Kennedy Xpy to Milwaukee: Dead, nobody out at all..

Update as of yesterday (1-19-96). Fulton Street between Ogden and Ashland. 3 good looking black girls. I finally picked one who gave a great blow job for 25 bucks. Had a mouth like a vacuum cleaner. I also agree about North Ave all the yuppies must have chased them away.

Subject: Chicago - scene Date: Sat, 30 Dec 1995 04:50:55 UTC

Your Chicago streetwalking section is impressive. I'll add one area that has not been mentioned, but it's not for the faint of heart. Essentially all of Cicero Ave. south of Armitage, extending as far south as the suburb of Cicero (south of Roosevelt) teems with streetwalkers, particularly when warm. The scene dies when it gets cold outside. The women range from butt-ugly to some that are quite attractive, so long as black ladies strike your fancy. Most are probably drug-users and the area immediately south of Cicero/Chicago intersection is particularly drug-infested. Therefore one has to be extremely careful. Nonetheless, I've found some great "nuggets" over the years. It comes down to gut-feel and luck. You can get ANYTHING for no more than $40. Needless to say, you have to be an extreme moron not to wear a rubber, better yet - bring some yourself. Many of the women are "casual" pros, I guess that's why they're referred to as "hoes". (by casual I mean they hook on the side to help support family, drug habit, etc.) Anyway, they're thrilled to get a white customer 'cause it means you'll pay to play. If a particular girl thrills you, you can probably easily make some other arrangements w/ her (like getting her #).

One part of the area I would NOT reccommend is the Madison Ave area, just east of Cicero. When they say "high risk", this is it. The talent further north is not as desolate/desperate. Best stretch is Cicero b/w North and Chicago .

Good Luck.......and be careful.......

Date: Wed, 17 Jan 1996 23:14:23 UTC

Chicago Streetwalker Scene -

As of 1/16/96 I could sum it up for you in 2 words: "It Stinks".

North Avenue - all the way from Damen to Clyborn is very dead. A new complex being built (I think Home Depot) has caused the cops to really sweep heavy - and I mean HEAVY. Needless to say, the working girls are not around there anymore (2 a.m. used to be the best time). Also, please be careful if you see a woman on the street that looks "too good to be true" because you may get busted by the lasted Cook County Sheriff operation called "Operation Angel" which is out to bust the JOHNS AND the WALKERS! If you get busted, you'll be bummed out - especially if you're married and dumb enough to have the car in both of your names because the police will impound your car (especially if you are a suburbanite) and it will cost over $500.00 to get the car back!

Now let me be honest - I have seen very good looking girls on North Avenue in days past (and even then it was very, very seldom and far between) what I usually did was watch the girl and see how she acts - watch her get in a car - then see if that car ever comes back to drop her off; if not, then it's a good chance that she was a sting and the guy is now bummed out. In any case, North Ave. has been predominantly dead for some time.

The same dead action goes for the Broadway Street area between Belmont and Diversey Aves., as well as Armitage between Milawukee and Pulaski, and Lincoln Ave. near the Lincoln Village Theaters.

All in all, action can not be found - if anyone knows of anything good - please post it! What you'll have to do is resort to getting less and because you'll have to rent a hotel room and pay more - $250 - $600 per hour is about average.

Good Luck!

Subject: Chicago scene Date: Mon, 08 Apr 1996 15:39:56 GMT

Was recently in the Chicago area and checked out the Cicero Ave scene (north of I-55) - didn't see any along Cicero until Roosevelt Ave (this was around 1pm on Friday the 5th. Had heard they'd done some cleaning up around there, but was approached by a curly-haired babe with a killer body. She wanted 25 for oral but I could've probably talked her down to 15. Didn't have the time or the money though.

Subject: Chicago:Warning, the heat is on. Date: 23 Jun 1996 19:51:01 GMT

Well, the already oppressive Chicago sex scene looks to be getting even worse. The city really seems to have it in for any street-level action. This week in the Chicago Tribune, officials announced a new penalty for people busted soliciting hookers. Not only will your car get impounded, a $600 fee just to get it out, but your name will be released to the papers. And don't think that you'll get off just if your out of town. Officials gleefully spoke of a recent man from Nebraska whose hometown paper was notified by the police department.

The area they specifically mentioned targeting was the portion of Lincoln Ave where it intersects Peterson. Looks like another area drying up. The North Ave strip is dead, Armitage west of Milwaukee has been dead the last couple times I've been by: lots of new, bright street lights and cops everywhere. The Wilson/Broadway area seems fairly active still, but I think it's only a matter of time before it falls. Cicero is dead, or swarming with police.

So Chicago area guys, where does that leave us? What towns surrounding Chicago are still relatively open? I know Chicago Heights is cracking down too. At this point I don't know of any good spots for streetwalkers in Chicago, much less outside of it. If anyone does, please post/email me.

Date: 1996/10/12

Street: Tried Fulton & Racine, no luck.

I did have luck on North Ave last week, weekday about 10p. There were some black chicks (I don't do them) and one white one. Yes, these girls won't win points for charm and beauty, but for $20, ya can't beat it.

Date: Fri, 10 Jan 1997 11:54:10 -0500 (EST) Subject: Chicagoland area


Street walkers at Roosevelt and Cicero: Prior to the following experience I had never been to a hooker. I often find myself driving down Roosevelt Rd. to avoid traffic on 290. There are usually hookers hanging out about 2 blocks east of Cicero Ave. on Roosevelt. One day I left work very early, about noon, and found myself where the hookers hang out. There were about six to choose from. Most very ugly, but one had a body that was perfect. Long legs, tight ass, every thing was working for this girl. She was about 28 years old and you could tell she lived a rough life. I pulled up to her and she came up to the passanger window. She asked if I wanted to have a "date". I said maybe. She then said it is $20 for a suck or $40 for a fuck. Since I had never before been to a hooker, this sounded real cheap. I told her to get in and I then followed her directions to a dark alley that was very scary. This was a noon, I would hate to be there at midnight. She then asked me for the money. I gave her $20, and then put my wallet in my pocket. She then unzipped me and made me put my pants down around my ankles. She then got a rubber put it on me and then began to suck me. She made me hold her tit with one hand and her ass with the other. She gave a great BJ. and I forgot all about life and safty. When I was done, she made me drop her off somewhere around 16th and Kostner. Another very scary nieghborhood. I pulled up to a corner and dropped her off. Her last words were, "Thanks, Your a gentleman and a scholar." It wasn't until I got home when I check my wallet, she had taken every last dime. 150 dollars in all. I learned my lesson.

Date: Sat, 01 Mar 1997 21:12:07 +0000 Subject: 3/1/96 Chicago info

Chicago is probably the WORST city for strip joints and prostitution, as the mayor here thinks he's the moral conscience of the world.

BUT, every large metro area with drugs will have prostituion.

Since the Chicago page isn't updated much, here is some updated info.

1) Wilson between Clark and Broadway (and the side streets) - there is action there...and mostly white girls..but this has become a major drug area and the cops are starting to crack down. Eye contact is key, as a working girl will always try to let you know that she's available. If she misses you, go around the block or something. After a couple passes, go on to the next girl.

2) Close to there...try broadway between irving (watch out for the Transvestite hookers (unless you want them) and all the way up to Wilson. Same deal as before...

3) Just north of Wrigley Field, by Irving and Sheridan, there is a dumpy hotel called the Carlos. Most of the girls who work this area live in this motel. It's cheap, and they sell Short Time. Recently, I heard that they are kicking the girls out, but you may want to go in there and see if any girls are just hanging around.

The above 3 listings area are all in the same area. Look on a map and try a route. You may want to try going up Sheridan from Irving to Broadway too. The uptown area of Chicago is getting a little tough, but contrary to other places in the city, at least 1/2 the girls working are white. I'm not a preacher, but please DO wear condoms as 10 minutes of pleasure is not worth getting Herpes or AIDS. Take in mind, that most of these girls get butt fucked by their slimey pimps 3x's a day, so wear protection! (Not to mention, almost 100% of the time, they are on heroin or worse.) If you are getting a blow job (bj - around 20-25, promise a tip and you'll get better service...afterwards..give them 5 or 10..and you'll be their hero! Fucks in the car are 30-50..but you can negotiate anything. No idea about Anal.) don't leave your wallet in your back pocket. Take the money you want to spend and put it in your ash tray or in your pocket. Hide your wallet in the trunk or somewhere where she won't find it. Some of these girls are master pickpockets. (This goes for anywhere, actually) Having been robbed myself, trust me.

In general, I don't pick up black girls. Not because I'm racist, but these girls have had the shit beat out of them all of their lives...they won't take any crap from you...and could probably kick your ass.

Do not go with a girl to her hotel room or house, etc. They may have a special surprise for you...and you may end up in a coffin. Yes, some of the girls are geniunely nice girls, but don't take any chances until you know them extremely well. These girls want to believe they don't work the streets, and will tell you they don't do drugs, don't have pimps, have real jobs, etc. If you believe them, you are very gullible. Always use caution. Don't give a girl your address, and certainly don't take her to your house. (at least not the first time.) If you do, keep your eyes on her the entire time. You may find something missing in the next few days!

Watch out for Operation Angel, the Chicago police initiative to wipe out prostitution. Contrary to what you may hear, the cops rarely cut the john's loose anymore, especially if the see you in the act. If your car is registered to your name, they will tow it and throw you in the local lockup and then transfer you to the main lockup at 11th and State for at least 5 hours. On Friday or Saturday night, you'll be there until the next morning. They have to "process" your ID and your fingerprints. (probably only takes 10 minutes, but believe me, they want to punish you as best as they can.) They've heard every sob story in the book. Then you'll have to go to the tow lot and pay 600 dollars to get your car out. It's a city ordinance that if you use your vehicle for prostitution, you have to pay a hefty fine. The way it works- it's not worth fighting it later. You have to pay now- to get your car + 22 bucks a day storage charge. You also have to goto court, of which time you may have to plead guilty in exchange for a fine and supervision, or they may just throw it out. They want you not to show they can issue a warrant for your arrest, etc. I know all this, because it happened to me. I'm not trying to scare you all, I'm just letting you know what the real deal is.

There are 2 ways they can bust you...1) You try to pick up a undercover...they stopped using girls that are "too good to be true" and often pose regular hispanic officers out on the street. Always keep a lookout for people just sitting around in cars, and especially in Chevy Caprices. They also don't have to have "M" license plates (Illinois), they figured out too many people recognized them by that.) The undercover will bait you until asking for what you want, i.e. blow job, sex, etc. Most likely they are tape recording. As soon as your bite, she signals the cops (waves her hands or something) and your car is surrounded. Your name will probably go into the newspaper too. An undercover will 1) never get into your car, since they don't want to risk her health or safety. 2) Will never (almost) initiate anything..she'll let you pull up to her, on the corner and she'll look in and ask you what's up...3) Will never show you anything like her tit, etc. (goes to say...)

The second way they can bust you is if they see you in the act. This is MUCH worse than just picking up a prostitute. Solicitation is just a ticket...not even a misdemeanor (although they will throw you in jail)..but prostitution...if they see you... is bad. Be careful.

Remember, that most girls need a quick fix of they'll tell you to park anywhere..on the street, etc. They just want to do their business and go get some crack. They don't want your love, stories, etc. They've heard that pretty woman story a million times..Don't let a prostitute sleep over unless you can watch her the entire time and take in mind, she may get up while your sleeping.

The best places to park tend to be in public parking lots, between cars... where alot of cars are. Turn off your engine, and make sure no one followed you. It's best to know where you are going to go before you pick a girl up. Most girls don't like if you drive around for an hour looking for a good place. Sometimes parking lots behind building can be ok, later at night (after 11 PM) ...before then, people are arriving home, and may see you...or you may be in their space. Whatever happens, make sure you can get out of where you are...and you can't get trapped in or something. keep all your doors locked. Sometimes the girls will ask you to drive them somewhere after you pick them up. I find the best thing to do is to give them a few bucks after your finish, and send them back in a taxi. I had one girl try to buy crack from inside my car (with the window rolled down) Trust me, you'll lose your car and be in much worse trouble. Don't let a girl leave and then come back at a stop...she's surely buying drugs.

If you do get caught driving a prostitute somewhere afterwards..or on the way... NEVER admit that you committed the act of prostitution. The cops know how to rouse the girls...since they probably know all of them...WELL. The girls know they are getting taken in...and the cop may work out a deal to get them out quickly or something. They will have no problem giving you up. (despite what they say). They will have you standing outside, and the girl inside the car...(a common police tactic) and get stories. Have a story and STICK to it. i.e. "I was eating at the hot dog place and so was she...she made small converstaion with me and later she asked me for a ride home... I agreed... (DO tell them where you were dropping her off, it will make you look credible.) I had NO idea she was a prostitute, and never did she solicit me for money or sex. I was just being a nice guy." They will say "she just told us that you took her home and got a blow job and sex"...and she knows where you live (which is why you shouldn't take a girl to your house.) Stick by your story...she may not have given you up..or even if she did... if you have a credible story and you STICK to it..not changing it... they will have to let you go. Although, they may take your name and license plate down...just so if they see you with another girl...they won't give you nearly as much play. If you admit to it...because you think that's what they want to hear..they just got the probably cause to search your car... and arrest you for at least solicitation and maybe prostitution. Don't expect to sue them for not reading you your rights... because they won't..and don't care. You can cry in the back seat, and they will probably only smirk at you. Chicago police aren't the most ethical...I'm not saying they are corrupt...but you can't trust them to keep a deal in general. If they do rouse you... they are at least somewhat honest, because they are looking for probably cause. If they are slime, they will just cuff you and the whore together and tow your car away.

Getting a cheap hotel room may be a good idea, but I recommend against getting one in areas frequented by prostitutes. The police know about these hotels, and if they see you pulling into the lot, you're caught. Spend a little extra money and go somewhere else. If the girl complains about time, tell her you'll take good care of her, and give her an extra 10-20 bucks.. that usually shut's them up.

Do not carry drugs with you, thinking you will entice the girl.. if are risking getting caught with a prostitute and drugs..and it's not worth me.

As I said before, use condoms..and keep plenty of napkins or kleenex in your car. Wipe yourself off afterwards, and the girl will appreciate that too. (she can wipe off her mouth, etc.) Better yet, go to your local pharmacy, and get some handy wipes.. (preferably, anti-bacterial) and really clean yourself off. Take your car keys out and piss outside your car. You can get herpes from casual contact...and although rarely- you can get HIV. If you use a condom, you cut down your chances of HIV to just about 0%. That girl may have given 10 blow jobs that night carrying a small bottle of listerine and asking her to rinse before may be good...if she'll do it.

I'm not condoning or encouraging the use of prostitutes...but if you're going to do it in Chicago, you have just about all the information you need. Here is some other information about other Chicago areas.

North Avenue... east and west of the Kennedy... the black girls are back around the bridge (that crosses the Chicago river)...this area has been well built up...and well lit. You know what I think about picking up black girls... and they are obvious...classic hooker garb.

West of the Kennedy, on North Avenue.. there is everything from black girls to mexican to white. Mostly black. This area (Wicker Park/bucktown) is artsy... and there are some cool bars around North/Damen. you'll see alot of gorgeous white girls walking in groups, etc. 99.9% of the time, they won't be hookers. I wouldn't waste your time..but you may get lucky. The side streets to the North of North Avenue...are places where girls often get off the highly visible North Avenue. If you make eye contact with a girl on North Avenue, she may signal for you to pull onto a side street, so to be less visible getting into your car. This area is generally ok, as there are more and more yuppies moving in, building gorgeous houses. There are also hispanic Either way, North Avenue is notorious for stings... so be careful. The vice cops will just sit there and watch a girl until she walks around a corner... and gets into a car. WHAM! you're busted. Or they will follow you until you park somewhere...and come with guns out.... Some of these cops are REAL pricks..just looking for a reason to shoot you or for any action.

The street parallel to North Avenue, one block North is Wabansia. Some girls walk on this street to...or between north avenue and wabansia on one of the side streets. You can make a big rectangle...or weave in between the side streets. Don't be too obvious though...and leave your doors locked. I've had a nasty black chick jump into my car at a corner..thinking I wanted a "date"... I did..but I was looking around for someone decently attractive!!! I wouldn't recommend going past Damen on North Avenue...any girls that far west tend to be ONLY black and you start going into the Humbolt Park area. (If you watch the show ER, several of their shootings happened in that area.).

Most of the time, the girls will be good from far...far from good. If she looks really strung out when she gets close, or stinks or alcohol or drugs when you open your window, etc. I would recommend that you move on. It's probably better to let the girl jump into your car..and talk elsewhere...but I roll the passenger side window down just enough so I can talk to them for just a few seconds... you can get a good read on the girl that way.

If you drive around an area a few times..just to get an idea of what's going on- that's a good idea. Especially, on different days... some girls are out during the day..and some out at night, some both. You usually won't see the same girl more than 2x's, if she's not a whore. If she is, you'll usually see her around... and sometimes with the exact same clothes on..that you saw her in before. That's a good indication that she's a working girl. Since the nights are getting so hot in Chicago, with the police. Many girls are coming out in the afternoon, hoping to pick up the business they make it through the night.

Don't be surprised if you drive on North Avenue and don't see anything at all. They may have rounded up the girls.. or it may be too damn cold for even an addict. Seeing a almost luck now adays..and can happen at any time...even at 7 AM... for girls who work the "bj before you goto work crowd."

Sometimes you'll see a girl, and want to take a few passes before you pick her up...just to make sure she's not a cop.. Most cops will stay within a certain area, as the area is staged for the police to nab you.. a girl walking down the street for a few blocks is "probably" not a cop. I've seen quite a few attractive girls this way (not only in Chicago, all over)..took a few passes, only to have some other asshole pick her up. I'd wait for an hour..and never see her again. (maybe that's all the money she needed,etc.) That's just how this business goes.. it's your choice... I recommend the cautious way of circling a few times..but you may lose out.

A few other Chicago areas...

Diversey - between Clark and Cicero. This is a LONG strip. The lathrop homes are along this strip, but there is only black girls there..if anything. Several miles down from there and by luck, I saw a gorgeous 19 year old white girl near the Marshall Fields warehouse and golden nugget restaurant. She was incredible and gave great head. She lived in a terrible apartment, but she was amazing. She eventually got evicted, and I lost touch with her.

Belmont and Cicero - This area has really died down..but you may get lucky. Drive up and down cicero between belmont and just south of diversey.

Cicero ave, south of North Avenue to Roosevelt - holy shit...don't drive this strip. It's about 7 miles of the worst black areas in the nation. Only trouble to be found there..

Cicero avenue - south of Roosevelt all the way down to Midway - you may get lucky and find a cute girl... but Cicero in general is a TOUGH area, and there is alot of political turmoil there, and they are "trying" to crack down on the prositution in Cicero (This is in Cicero, a suburb of Chicago, right next door). So be careful. Around 31st or so, there is a dunkin' donuts....and sometimes girls will be inside there... try to make eye contact with them, and they will come out or maybe you can go in to get some coffee..and make small talk, etc. There are a few cheap motels on this strip, and girls tend to hang out by there.. I would recommend that you drive this strip, and not walk it. (not to mention, it's about 7 miles long!). Hookers tend to walk by themselves....and there are alot of black nasty hookers around roosevelt and cicero avenue too... everywhere you go, just about all of the or white are totally strung out.

Strip Joints -

As you can imagine, Chicago sucks for this too. But here is a review.

Bare Assets - there are 3 of these places around in Cicero, one on Halsted-loop area, and I think one on Clark. These are basically jack off buy tokens and go into glass enclosed booths with small slots to drop dollars into. If you want a decent show, the girl will hassle you for 5-10 even 20 dollars...definitely not worth it. These places are LAME.

Crazy Horse Too - used to be Thee Doll house - a chain of strip joints from Floriday. the girls here are GORGEOUS..most of them are model types.. and they serve full liquor. It's 10 bucks to get in, and dances are 20 bucks...expensive. The drinks are expensive too. It's on Kingsbury, just south of North Avenue. This place is totally on the up and up, and the girls here wear pasties on their breasts...and g-strings. If you need to entertain a corporate client, this is the place to go. Very upscale and expensive.

Admiral Theatre - on lawrence. About 25 minutes from the loop, but the girls here are gorgeous too, and tend to be younger...just out of high school is common. They go totally nude there, but there is no liquor. They have headliners all the time, like pornor stars, etc. Dances are 10 dollars.. the girls are scrumptious! No touching, unfortunately. This place is also very nice and upscale. Much larger than the Crazy horse. They also have a porno bookstore, and upstairs..they have porno movie booths, etc. 15 dollars to get in, plus you have to buy 2 drinks at admission... for 3.50 just to get pay 22 bucks.

Pure Gold and Doll Lounge in Cicero. The same guys own both clubs...girls range from butt ugly cattle to some pretty gorgeous ones. The girls used to dance on stage, but as of 1/1/97, they didn't get their entertainment license renewed. They did get their liquor license renewed what the girls do is go around, and hassle the few people in there to buy them drinks (8 or 24 bucks, depending on how long you want the girl to stay with you and talk.) and you have to tip the pushy bar maids / waitresses. The girls only get 1 dollar and 3 dollars respectively for these drinks. They want you to take them into the back (both clubs work the same) and either do a 50, 100 or 150 dollars "dance". (I guess they can still do private dances..) The bar maid who takes you back, expects at least 10 dollars for the 50 dollar dance, 20 for the 100, and 30 for the 150. They get pushy about this. I've blow alot of money at these trust me- I'm a pro. At pure gold the "private dance" area is like a short hallway..and for 50 get a table and chair... near to the entrance...there is a silver "string-type" curtain, that people can see through.

Pure Gold has better looking girls and younger. The doll lounge is bigger, and they have some decent girls too. Pure Gold used to be open from 7 PM to 4 AM, but now from 7 PM to 2 AM.

The Doll Lounge is open from like 4 2 AM... (used to be 5 AM). The private dance area is the same policy as pure gold, but the back area is actually much nicer. There are about 5 little rooms, totally separate from each other.with string curtains..but much thicker...much more private. There are some really cute hispanic girls who work there..but some of them will hustle you for tips in the back.. and I HATE that. If you give the bar maids decent tips when you get drinks..(they do serve alcohol there..with full nudity in the back, since it's Cicero) they may give you good tips on who to go back with...if you ask. After all, they know all the girls..and they appreciate your tips.

Girls come and go from both places, but there are really some gorgeous girls at Pure Gold. Some go...and come back in a few weeks, etc. There are always the stable girls there...(some of them not bad, at all!). Lisa is a hispanic looking (light skinned) girl who is actually polish...she has an incredible body (very busty, shapely, playboy model type body)..and she does great dances.. Candy is gorgeous too..but not as shapely... Adriana has a full figured, body built for sex...huge knockers...nice tight ass... (none of the girls I'm describing are fat) but she only works Monday - Thursday. Adriana isn't that great in the back...but you might want to try her. The other regulars aren't that great.

Well, that's all I know about Chicago streets and the strip clubs. I hope this information helps you. If you have questions, please post them to and I'll try to keep up with the board, but time constraints, etc. may make me miss something. Keep posting your question and put "CHICAGO" in the subject line..and I'll do my best to get back to you. Thanks to Atta and M for having the balls to do what most others won't do! If you know of other areas, don't be a pisshead, and post them! Too many people just suck the information and don't share it. IT sucks that a.s.s. and a.s.p. are 99.5 % SPAM. I've heard about the Central Park/Armitage area..but I haven't been there...any body know anything? or any other area in Chicago? I've called a few escort services in chicago...and damn..they want 300-400 dollars for the hours... no thanks. I've heard the Reader newspaper has ads for independent girls who charge much less. If you know of anybody or have a review...please POST! Also... since those 2 clubs in Cicero lost their license to have girls dancing on stage.. many girls have left..and some have alot of customers..who just went there to see the show. (no cover, but you have to buy a drink an hour) So if you go in, expect to have alot of girls come up to you and ask for a "private dance or drink". You can always say NO. It's your have the freedom to choose...after the Cicero elections in April 97, they should be back to normal... politics suck. I can say that the days of stripjoints aka brothels in Cicero is LONG gone...

Also, I'm looking for updated info on NYC street action and incall places. It's only fair that those who use this information post information. PEACE.

Date: Mon, 31 Mar 1997 Subject: Chicago info

First off, great thing you're doing for all of us! Keep up the good work! I figured I'd do my part and contribute, so here goes...and if you want to use the email address, go ahead....up to you. It's a dummy account, so it's fairly hard to trace back to me. (smile)

Things seem to be available in Chicago, but it's certainly not open like it is in Washington DC or New York or Atlanta. I've gotten a few $20 blowjobs from two girls in the past month. One was a white gal, about 35, with very small tits and the ugliest face you've ever seen. She was a great cocksucker, and didn't use a condom and did swallow. She was walking along Mannheim Road, between the Days Inn and Marco Polo Inn. I checked into a hotel, and took her to the room. She was drunk off her ass, and I think did this more as a hobby than anything. I gave her a $10 tip, and she wanted to fuck me for $20 more...but I just couldn't do that. She was really ugly.

The other gal was also about 35, average tits and semi-cute face. She was walking along Cicero Avenue about four blocks from Grand Avenue South. It was about 10pm, and she was just walking around, but the second time I passed, she waved her hand carefully at me. The cops are pretty openly against prostitution there. I pulled over, she walked around the corner and then got in my car. She wasn't drugged, wasn't drunk, and admitted that she hated prostituting herself. But then she asked me for $25 bucks, and I offered only a $20, and she said maybe I could tip her. We got to a dark alley, she blew me, and then spit the cum onto the sidewalk beside my car. She was cute (as far as prostitutes go), but I was running late, so I split.

Moral of story is ... guys, it ain't dead out there...but you've gotta be REALLY careful. Things are tight in the windy city.

Date: Tue, 21 Oct 1997 Subject: Chicago "Wrigleyville" Status

Here's some walker info (Oct. 1997) for anyone who cares.

Parts of the Chicago, Illinois, "Wrigleyville" area (see Chester's Report for details have become a bit promblematic. (though this are is still one of the best places to go) Near the CTA "Red Line" Sheriden stop, there have been a number of top-notch looking girls walking around... Unfortunately, dispite their attitude and dress, they are not walkers. They are fashion students (attending Illinois Institute of Art in the Merchandise Mart) who now reside in Park Place Towers (655 W. Irving Park).

They walk around in previously prime areas Sheriden, Addison, Broadway, Halsted, Irving Park, and surrounding areas.) and may give a look or two in your direction. They're kind of stupid and can't understand why they are approached so often. As of late, they've been getting vindictive (police reports, mace, etc.) resulting in more CPD (blue and vice) coverage. It's adviseable to watch out. Best bet is to have them come to you by mean in a good FAQ.

Carlos Motel is still a decent place to go if you don't want to waste time scouting the streets.

Stay way from the touristy parts of Belmont (around Clark). If you do run into anyone, more often than not it's a boy. It's where the younger members of "Boystown" like to play dress up, so even if you are looking for their company they are usually not available.

Further up Broadway (up to, and around Fullerton) the game becomes a bit sparce, but when you do snag one it's usually quite a prize. Near DePaul is like this (just be careful of cops and security), though near Childrens Hospital you get some feral black women.

Unless you really need to feed a fetish, New Chinatown (Argyle) isn't a hot idea. While I haven't heard anything too solid, there are rumblings about girls working bushwhackers who get you while you're parked. If you do pick one up, drive around to make sure you aren't being followed and then park a little further South (expect to pay a little extra for taking a girl out of her way).

Good places to park are all along the Red Line from Wilson and beyond. Don't go much further than Kimball (best stick to the Ravenswood "Brown" line). Remember to scout out a parking place before you go hunting. It might even be a good idea to "stock up" your parking spot with hidden goodies (my personal fave is a flare "gun") in case of trouble. If the shit hits the fan, use whatever tactic you need to get to a populated area fast. CTA stations are prime.

Subject: Chicago update Date: Wed, 19 Nov 1997

I have done a fair amount of research on the areas in Chicago mentioned in previous postings. All I can say to those who've expressed disappointment is: be patient.

First, the West Side. Madison from Damen to California is a spotty area now. This is past the United Center. East of the UC is dead, since this area is now largely yuppie (last two years this occurred. On Madison, hotspots are Leavitt/Oakley Blvd., east of Western Avenue, and the few blocks between the freight tracks and California. These women are exclusively black, and the area is very dangerous. Nevertheless, $10 blowjobs are to be had here. I imagine that anything goes in this area, but blowjobs are the extent of my knowledge. Anytime of the day or night, but be careful.

Also on the West Side is Roosevelt Rd. from Kostner to Cicero. This stretch includes Cicero north and south (to be avoided), as well as a sliver of Cicero (Village) just south of Roosevelt, and the first street north of Roosevelt, heading back into Chicago. Along this stretch, any attactive women you see (I mean clear skin, nice clothes) will be the police. Otherwise, get off the Ike at Kostner and head south. At Roosevelt head west. All side streets between Kostner and Cicero have potential action. Some absolutely excellent, some pure scam. Keep cash in your pocket, your driver's license in the car, and your wallet at home when coming here. Blowjobs should never exceed $20, unless the woman has huge tits, a tiny waist, a reasonable face and a throat you could shove your forearm down. Then $30 could be considered a bargain. In this area, it is again anytime of the day or night. It is not a good area, but Roosevelt itself has no residences, and is almost all factories, so random violence is minimal.

On the North Side, there are several areas to explore. First is North Avenue between Sheffield and Damen. This is a long stretch, and really is two different areas. Sheffield to Elston is more classic hooker garb. From the Kennedy to Damen is lower key.

From Sheffield to Elston, black women predominate. The occassional white girl usually only lasts out there about 30 seconds. The problem in this strip is that there are many police, but it is a wide strip with no side streets, so cars are heavily exposed from far away. An alternative is to park (the area is largely safe) and walk the strip. A $20 blowjob can be had behind the railroad cars parked on a siding, on a bridge stairwell, or in a Home Depot stairwell, for instance. This will not keep you from getting arrested, but it should keep your car from being seized. I have no knowledge of the women here being anything other than enthusiastic and honest. The fetish-hookers (ie all latex) are more expensive, but apparently will let people cum on this latex. Depends what you're in to, I guess... This area is seven days a week, but only late (from maybe midnight to five a.m.)

From the Kennedy to Damen, on the north side of the street, there are a few hot spots. The block at the gas station is one of them. The girls here tend to be white or Latinas, and dressed less like classic hookers. The previous postings have covered this area. It appears to be from about 9 p.m. to one a.m. By the way, if you think a "hooker" looks so good, you'd pay anything to nail her, she's probably a Bucktown yuppie from Kansas or somewhere.

Much further north, at Lincoln and Jersey, there is a reasonable amount of action, but I haven't quite figured out the timing. Nevertheless, a tall, beautiful, young black girl who could suck the chrome off a bumper hangs up there. I suspect that the large number of crappy motels in that area are tied to a decent trade, but I'm not yet sure how these work either.

The areas discussed in a previous posting north of Wrigley Field are tough, since the police are heavily into this area. However, there are a few women hanging around, including on Grace, heading back west (?) from Sheridan. This street is very dark, but pick the girl up quickly, since the police are never more than about ten feet away.

Finally, at Lincoln and Foster, behind the Dunkin Donuts, there was a blond girl, maybe 19 years old standing around about 4 a.m. She was very, very cute, and still had no idea how the street scene works. Suffice it to say, I'd never heard of a hooker who had a dick in her mouth, two fingers in her puss, and a thumb in her ass for $20, in the backseat of a Ford. If she's there again, she is massively recommended.

Keep up the good work.

Date: Fri, 23 Jan 1998 Subject: chicago




Date: Tue, 10 Feb 1998

Hey Guys,

Well, I had some time tonight so I decided to check out the Chicago street action.

It was really foggy tonight, which makes for great cover for getting a blow job in your car!

I started the Cicero strip and saw one really short white girl around the Cove Motel and several black girls around Cicero and 290. Nothing south of 55.

I then cruised North Avenue and saw nothing.

For the first time, I checked out the Armitage and California scene. It was around 11 PM and around 33 degrees.

There was one 30ish blonde with a decent body and a younger looking (young 20's) latina. Unfortunately that was all I saw. I decided to try the latina but when I turned around she was getting picked up by another car. Damn! I then decided to take another look at the blonde and she was gone too....SHIT!

I then drove the Broadway / Irving area and saw nothing. Was tempted to drive up to Lincoln / Peterson but decided against it.

Decided to try Diversey for the first time in a year and drove from Broadway all the way to Cicero. Nothing.

Drove back to Armitage ( around 1 PM at this time) and nothing... drove down to North Avenue and saw one nasty black girl. Took one last drive down Cicero avenue and saw several different black girls around 290 and Cicero and one older white woman around Cicero and 47th.

Got some burger king and then headed home around 2 PM.

Can someone give me some good info on the armitage scene? I just drove on Armitage, didn't try any side streets (looked kind of scary) or cross streets. Any hot dog joints where they hang out at? The area looks promising, but I did pick up a girl on North Avenue about a month ago who usually works the Armitage / California scene and she "says" that the cops are cleaning up the area. I didn't see any on Armitage, but of course North Avenue had the usual patrols.

(the girl I picked up a month ago wasn't worth mentioning...)

Haven't seen Maria for a long time, but I haven't exactly been around.

I am now deciding whether or not to move to New York (permanently) for my job. I live there around 3-4 days a week now, so I guess I may as well. Keep the emails alive... share the information and the jollies...

Date: Sat, 14 Mar 1998

Chicago: Street hookers are on Madison Ave. west from the United Center to Cicero with a few now show stretches. They are also on Ciecero Ave. from Madison North to North Ave. They can also be found on Armitage From Cicero Ave. East to California. They are harder to find in this stretch but you can find them. In Chicago a blow will run from 15 to 25 and sex from 25 to 50. The looks are from a 0 to 9. Many do it just to get money to feed the family. Make sure you don't have your wallet or money accessable while getting head as some of the girls are also good pick pockets but most want to do you and get on the road as they are serious about making a buck.

Prostitution, Prostitutes, Escorts, World Sex Guide

HOME | Top | Chicago | Archive Index |

Copyright 1997-2013 WSG Properties User Agreement | Legal Notices