The market for Chicago escorts is one of the most comprehensive in America.

Whether you are looking for a high-class courtesan to take out for dinner in downtown Chicago, or sexy call girls in the suburbs of Buffalo Grove, Wheaton and Lisle… there are a number of escort agencies and freelance private companions who can give you exactly what you desire. And probably much more.

Below we have compiled a complete guide to the Chicago escort scene.

Scroll down for the best agencies, private companions and even some sexy social media accounts that are worth following.

A Guide to Chicago’s Best Escort Agencies & Call Girls

Chicago escorts and sexy private companions

A guide to Chicago’s best call girls and private companions.

Chicago Escort Agencies

Let’s start with some reputable agencies…

Skyline Companions

Skyline Companions Chicago

Phone: +1 312-880-7599

The Skyline Companions roster is an international mix of women from all over Europe, with a few local Chicago girls for good measure.

We spotted a number of models from Italy, Ireland and Germany, alongside various Latina beauties. All of the girls are available for hire at evening events, private functions, over romantic dinners or for a ‘fantasy overnight’ stay where we’re sure you can connect the dots.

This is not a cheap agency, as reflected by the rates below.

Skyline Rates:

  • Exotic models: $400 to $450 per hour
  • VIP Centerfolds: $550 to $650 per hour

Keep in mind that a dinner date booking is likely to last 3-4 hours, possibly longer if you agree to extras.

Hiring a VIP Centrefold grants you VIP membership with the agency. These ladies are the creme de la creme of the escorts on their books. Sophisticated and beautiful.

Chicago Babes

Phone: (312) 337-6969

Chicago Babes is a 24/7 escort delivery service that claims to be able to deliver a lady of your choosing to your hotel door within just 30 minutes in the Downtown area.

This agency has a broad selection of call girls; both local Americans and a lot of European ladies too. The website has profiles for each escort with a few photos (non-blurred) and a brief description of her background and personality. Pretty vanilla though, as you’d expect.

Babes Rates:

  • Anywhere between $100 to $1000 ‘donations’ for the lady
  • Agency takes a ‘matching fee’ of $200, paid by credit card

Chicago City Escorts

Chicago City Escorts

Phone: +1 773-488-6969

This agency has been around for over 30 years, and to be fair, it looks like their website was designed about 30 years ago too. We only just about managed to find the exit from their splash intro!

They have a selection of blondes, brunettes and redheads available for hire. There are various reviews suggesting that you can enjoy a very nice GFE (girlfriend experience) or (PSE) pornstar experience with these courtesans.

You’ll find a few profiles on their site. Each has three-photo shoots, her vital stats (age, height, weight, cup size, waist size, etc), and details on which areas in Chicago she serves. All of the girls we saw were available in downtown Chicago and the nearest suburbs.

No signs of any rates listed.

Wet n’ Wild Escorts 

Phone: (312) 217-8543

Wet n’ Wild claims to be the number one ‘No Bullshit’ agency in Chicago. A cause we can definitely get behind.

This agency offers both GFE and PSE with a large roster of exotic escorts. There are plenty of European girls listed, but also some South Americans and Latinas.

Various highlights from their roster include a petite spinner, a PSE Cougar of the Year, a couple of rare Indian escorts, and even some Arabic girls.

No rates available on the website but there is a discreet booking form where you can get a quote for your exact requirements in Chicagoland.

High Class Chicago

Phone: 312-401-3422

They say ‘high class’ and they mean it. This is strictly a luxury high end courtesan service. Their brand is splattered with Champagne flutes, private yachts and private jets… not the sort of vibe where you’re going to find ‘competitive’ rates if you are hunting for escorts on a budget.

High Class Chicago Rates:

  • 5 hour dinner date: $1500+
  • 8 hour overnight special: $2000-$3000
  • Fly Her Anywhere (24 hours): $5000 plus airfare
  • Weekend Getaway (48 hours): $9000 plus airfare

This is one of the few agencies to provide listings of their ladies with the exact donation she expects. Sure enough, they have some beautiful call girls on their books.

Windy City Girls 

Windy City Girls

Phone: 1-800-805-9957

A selection of students, bikini models, fashion models, fitness instructors and even some actresses on their books. Windy City Girls are young, beautiful and ready to keep you entertained.

They promise quick arrival times — within the hour for Downtown Chicago and the major metro areas.

The ladies may still be able to travel to the outer suburbs but this is likely to incur extra travel fees. There are no rates listed on the website. You are asked to contact them regarding the ladies on their online roster and they will give you an idea of the expected donation for her time.

Five Star Companion

Phone: (321)  724-9162

They hire only young and beautiful companions in Chicagoland. These escorts are chosen not just for their looks, but also for their wit, intelligence and personality.

Five Star has a useful roster page with each of their available ladies listed, including teaser photos and their current rate per hour. It seems to be a mix of Native Chicago girls and few international ladies. Some sexy Latinas too.

Most girls seem to be in their early 20s. The majority offer GFE but you’ll have to call ahead to discuss any specific preferences you have in mind.

Independent Escorts in Chicago, Illinois

You don’t have to go through an agency to arrange a memorable evening with one of Chicago’s sexiest escorts. You can, of course, book a courtesan from the freelance ‘independent’ scene.

Here we have gathered a list of Chicago’s independent escorts who have an active web presence. Please note: for privacy reasons, we won’t be publishing their direct contact details. Instead we have linked to their personal websites where this information can be found disclosed on her (or his) own terms.

Alexa — Alexa is a tall, slender blonde with a natural and elegant appearance. She regularly tours around the US and is often available for Chicago bookings. See her website for her latest schedule.

Gypsy of Chicago — Gypsy is an attractive full figured Chicago companion who provides an intimate GFE, described as genuine and affectionate, as well as having a submissive streak.

Mya Michelle — Mya is an attractive bisexual courtesan offering companionship in the Chicago area. Petite and busty, she is described as an intelligent and fun-loving girl.

Marissa Morgan — A luxury travel companion and tall stunning blonde; 5’10 with long legs.

Marina in Chicago — Marina is an all natural curvy and busty Nordic blonde. She is 5’9″, athletic with piercing sky blue eyes. She also has a blog with stories and excerpts on tantra, sensual massage and erotica.

Alyson Parker — The ‘body of a 1950’s pinup girl’ and in possession of a fiery sensuality. She says she offers classic private companionship for the modern man.

Veronica BBW — Sexy southern BBW beauty offering both incalls and outcalls.

Sophie Sapphire — Auburn-haired beauty and luxury companion who is available in Chicago and Central Illinois. Incalls accepted in Lincoln Park, Schaumburg and O’Hare.

Leila Namazi — She is a darkhaired beauty native to the Chicagoland region with a Midwest ‘girl nextdoor’ charm.

Misha Cox — Attractive black girl, available for bookings with gentlemen as well as couples in the Chicago region. She says she is open minded and enjoys kinky sex, including light BDSM.

Tantra Butterfly — Goddess Diana is a skilled practitioner of tantra massage in the Chicago area. She offers a variety of erotic massage services with the typical session including tantra, Swedish and light energy work.

Diamond St. Clair — She is a sweet and sexy BBW latina who can be as ‘wild as a lion or gentle as a kitten’, depending on your preference. Available for bookings in Chicago and Illinois.

MILF Montero — An erotic blonde bombshell offering companionship in both Chicago and New York City.

Lilisse Palmier — A luxury private companion and a strictly high-end courtesan; pretty and petite. She says the first impression you may have of her is “little doll”. Only accepts bookings from gentlemen over 35.

Ann Cline — Sexy GFE blonde escort available in all major US cities, as well as worldwide. She spends a lot of time travelling the States so check her schedule in advance if you want to make a booking.

Available for bookings in Chicago/Illinois and want to get listed in this section? Drop us an email and we will add your details.

List of Chicago Escorts on Twitter

We still remember the days when the closest you got to ‘knowing’ an escort would be to spot her number scrawled in a phone booth. These days, social media makes it easier than ever to stay connected to the hottest call girls (and the slew of erotic images that she might publish…)

If you are looking for Chicago courtesans to follow on Twitter, check out our updated list:

@MILFmontero1446 — One of Chicago’s hottest MILFs; also available in NYC area.

@Miss_Erin_Black — BBW GFE (girlfriend experience) and kinky companion with a lot of tattoos and a lot of curves.

@MissLolaLuxe — 22 year old bisexual Caribbean courtesan who is available in Chicago, New York City, LA and other major US cities. Tours often.

@Isabellachicago — Dark haired mature stunner with voluptuous curves.

@MyMyaMichelle — Busty petite escort offering one of the ‘best GFEs’ you are likely to find in Chicago.

@AllStarAllie — Cute looking ‘girl next door’ type who says she wants to fulfil your fantasy. Offers GFE.

@InaraLorde — Sophisticated modelesque 24 year old ebony stunner. She’s a professional companion with a geeky side.

@Gypsy_ofchicago — A luscious ‘girl next door’ courtesan who tweets regularly and is available for bookings in the Chicago area.

Are you a Chicago/Illinois escort who maintains an active Twitter profile? Drop us an email and we will add your details here.

Finding Call Girls on the Classifieds

If you are experienced in the punting game, you will know that a very large percentage of the escorting business is driven online through adult listings of the popular classifieds.

Here are the two main sites:

Craigslist Chicago

Craigslist Chicago Sex Ads

Craigslist is an online metropolis of rental ads, job posts, community group and random wares for sale. But if you want to know what really drives the traffic to this site, you need look no further than the section marked Casual Encounters:

Casual Encounters on Craigslist Chicago:

Here you will find hundreds of sex ads posted every day, most of them by escorts offering up various types of full service, but with plenty of others from johns posting ads for the exact service they want.

If you want to live out your fantasies and fetishes, you can post an ad here and receive a swarm of replies from call girls who are willing to oblige.

The danger, of course, is that ‘your mileage may vary’ completely understates how variable the eventual service may be. Will she look like her pics? Is she who she says she is? Is she answering through her own free will, or does she have a pimp?

Craigslist Chicago is the most active online community for picking up escorts, but you have to be careful.

A couple of bad experiences and you’ll soon see how the top escort agencies earn their dollar. The ‘middleman’ does a lot of filtering in this business.

That said, whatever you are looking for — M4W, M4T, M4WWWWW, WFM — you will find it on here.

Backpage Chicago

Backpage Chicago Sex Ads

The closest rival to Craigslist for adult personals is Backpage.

While most categories on Backpage mark down how many ads they have inside, the Adult section in Chicago has so many sex requests and hookup offers that the number no longer appears. Too many to keep track.

Every day there are hundreds of listings posted. Some are by independent escorts looking for a needle in a haystack (aka, a normal client in a sea of weirdos), others are by agencies looking to promote the various ladies on their books.

You’ll even occasionally find ads posted by women who just want to meet up for no strings sex. Hey, it’s rare, but it does happen.

Backpage is sort of the bottom of the Internet when it comes to searching for escorts. While you can find every adult service imaginable, there’s no guarantee that you’ll get what you’re looking for — or the right girl, for that matter.

It is what it is though.

Many men are mesmerised by the choice on offer. They will spunk entire evenings combing through Backpage Chicago for the perfect lay; passing up hundreds of strange requests in the process.

Sometimes they even find that perfect lay.

And for a fraction of the price of going through an agency.

It is what it is.

Note: If you are not based in Chicago, be sure to check out the other Backpage portals for the surrounding areas. They have sex listings in Bloomington, Chambana, Decatur, La Salle County, Mattoon-Charleston, Peoria, Rockford, Springfield and other parts of Illinois. You can also filter by the whole of Chicago, or regions: e.g. North Chicagoland, South Chicagoland, Northwest Indiana, etc.

If you are going to use any of the adult classified portals, our advice is to tread carefully. Don’t believe everything you read. The tips below may help…

Tips For Hiring a Chicago Escort

Whether you are hiring through a call girl’s personal website, a trusted agency, or one of Chicago’s top personals postals… here are some tips to keep in mind.

Be aware of the screening process. And respect it.

Serial Johns would be amazed how many people contact us to complain that an escort was trying to rip them off because they wanted to check their identity prior to the booking.

(Not that we can help them in this regard. We are not an escort agency!)

The simple matter is that escorts have a duty to take their safety very seriously. Put yourself in her shoes. You’re knocking on the hotel door of a complete stranger not knowing who or what you’re going to find behind it.

Screening isn’t a bad thing. It’s a very good sign that the lady you are meeting takes her business seriously. In fact, the alarm bells should be ringing if the lady you are meeting sounds keener to meet than you do.

Negotiate before, not after, the service has been delivered.

Another rookie error that leads to all kinds of problems.

If you are hiring an Chicago escort for the first time, it’s up to you to communicate what you are looking for before the service begins.

To try and change the rates after the act — just because you didn’t like X, Y or Z?

That’s likely to get you blackballed.

Stick to agency girls and prominent freelancers if you have the budget.

We know a lot of escort users love the cheap rates that can be found on Backpage and Craigslist.

But what cost for some peace of mind?

That’s part of what you’re buying by going through an agency, along with — in most cases — a much higher calibre of lady.

If you don’t want to use an agency, it’s just as good to go through the personal website of a freelance ‘private companion’ who has a history of good reviews and a large social following.

You know what you’re going to get in these cases.

If you can read other clients’ reviews… even better.

Chasing explicit paid sex offers on Backpage is a good way to get yourself caught in a sting. The best escorts will say no such thing in black and white terms. Not in public, anyhow…

Stick to outcalls

Chicago brothels are not the licensed legal sex spas that are common in other parts of the world. Neither are the private apartments of known prostitutes.

It’s generally much safer to stick to using outcall escorts.

Outcall escorts = Those who come to your hotel room or private residence.

This way, you control the environment. While the lady might not be ‘as specified’, you can at least maintain control of everything else. It’s one less factor to worry about.

Looking For Something Different?

We’ve compiled several guides showcasing the best of Chicago’s adult entertainment — including the best strip clubs, escort services, massage parlours, sex shops and swinger clubs.

Don’t want to leave the house? You can always rely on cam sites like Chaturbate and Bonga Cams to keep you entertained without leaving home. These communities are full of amateur models happy to put on live cam shows for your pleasure. Worth checking out.

What’s your favorite escort agency in Chicago? Are there any call girls or courtesans that you can recommend for our readers?

Have your say below.