Rentboy – Largest Gay Male Escort and Massage Site

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex





83 male escorts and male massage therapists In Chicago, Illinois

card grid realtime
page of 5

Sorry!

The ad you tried to reach is no longer available. Below are ads in the same location as the ad you tried to reach... or try searching again.

For All Those Whom Got More Air Than Love

First and formost I would like to thank the 1.5 million viewers for ranking my performance one of the all time highest rated & most watched in pornhuBB history.  Never saw that coming.   That said, if you know what you like and like what you see...then indulge yourself. SXVideo p... (more)
Chicago, IL
My Phone Number
Mobile+1 (773) 606-9929
Email
In Rate Out Rate
$250 $225

New in Chicago!

Face and additional pictures are available per request. Laid back, confident, very good looking. Over all great guy. Southern born and raised, accent and all. I genuinely enjoy what I do, so I have no doubt you'll enjoy what I do too. I respect everyone's privacy and any encounter is between us. Fee... (more)
Chicago, IL
My Phone Number
Mobile+1 (404) 860-1213
Email
In Rate Out Rate
Ask me Ask me

VISITING CHICAGO / MAR 5 to MAR 9 | HUNG THICK * MASCULINE * FRIENDLY * TOP

38, Italian/Lebanese, 5'8", 150#, 29"w, Hung thick 8x6 cut, lean and muscular. Clean cut sometimes with a little scruff, masculine, discreet, friendly, uninhibited, top. Reliable and uncomplicated. Excellent reviews.Private gallery password:  HUNGArrogance and attitude free. I treat men of all ... (more)
I'm #1 on the map travel adChicago, IL
My Phone Number
Mobile+1 321-287-4568
Email
In Rate Out Rate
$250 $300

ADULT FILM STAR THAT LOVES SEX , SEX AND SEX !!

I'm a muscular jock that is well traveled, passionate and wild with a heart of gold ! No attitude or judgements. I can be extremely affectionate, romantic and I love to kiss. But if you're looking for something a little more wild, rough or if your into leather fetish or any other fetish I'm your man... (more)
I'm #2 on the map Chicago, IL
My Phone Number
Mobile+1 773-413-8086
Email
In Rate Out Rate
$225.00 $250.00

One of the BEST TOPS in Chicago!

I'm a hot and passionate companion. I can get into intelligent conversation over a nice dinner as easily as I get into sensual play. You will find that I am dependable, professional, real and easy to get along with. I enjoy theatre, travel, fine dining, shopping, movies, and more.  I returned t... (more)
I'm #3 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 870-2154
Email
In Rate Out Rate
$225/hr $250/hr

FARM GROWN BUCKING BRONCO- MAKE YOU R RESERVATIONS NOW!!! 5 Days ONLY!!! FEB 02/18 to 02/23 (303) 359-3192 WWW.ELIDANIELSENTERTAINMENTNETWORK.COM

***CHICAGO AREA for 5 DAYS ONLY 02/18- 02/23 & booking apts before I arrive***LOVE WHAT I DO, HOW I DO IT, & WOULDN’T CHANGE A THING ABOUT IT......I’m not a porn star by choice but definitely down to make some memories on camera…Visit My Website to see some memor... (more)
I'm #4 on the map Chicago, IL
My Phone Number
Mobile+1 (303) 359-3192
Email
In Rate Out Rate
$250 CASH or CREDIT $300 CASH or CREDIT

Discrete | Masculine | US Marine | Chicago till March 11

Currently in Chicago till Mar 11My name is Mike, I am a ex US Marine that is passionate, down to earth, laid back, real, and easy to talk with and most important fun to be around. I'm 5'9 185/lbs, workout 5-6 days a/week. Are you looking for something vanilla to a little more wild? Got a fantasy? I ... (more)
I'm #5 on the map Chicago, IL
My Phone Number
Mobile+1 (312) 647-6567
Email
In Rate Out Rate
$210 $230

You have stepped into the erotic zone

Tall,Dark,and Handsome Prince looking to relieve you of all your built up tensions, give you the most exquisite pleasure,and take you through the most ultimate experience.Built like a "Super Hero" and hung like a " PornStar".Seriously! Doing In-Calls Out-Call$250.00 an hour $1000.00for day.Call me ,... (more)
Chicago, IL
My Phone Number
Mobile+1 (312) 344-3052
Email
In Rate Out Rate
$250.00 1 hour $250.00 1 hour

As seen in Raging Stallion's "Young Warriors"

I am a sociable, fun, down-to-earth & down-for-whatever guy who is the perfect companion for a night on the town, a lazy afternoon at home, or any other kind of fun you can imagine. I am a college student who models and does adult films. I am everything you can possibly ask for in a companion: A... (more)
Chicago, IL
My Phone Number
Mobile+1 206-681-3304HomeNO BLOCKED CALLS
Email
In Rate Out Rate
$200 $200 + cab

Warm up :D

Let me know what you have in mindtext/email preferred  
I'm #6 on the map travel adChicago, IL
My Phone Number
Mobile+1 (312) 854-9204
Email
In Rate Out Rate
Ask $180/hr, 300/2hrs

Looking for the complete package?

Hot young latin stud with a great personality. Pretty much into everything safe. I can be your fantasy romantic boyfriend or your passionate fantasy porn star. love kissing, j.o. Lots of body contact and fucking. Top > STATS > 27yo, 6'1", 175lbs, tan skin, athletic , smooth, 9"uc. Visiting chi... (more)
travel adChicago, IL
My Phone Number
Mobile+1 917-328-5207
Email
In Rate Out Rate
$250 $280

12 Inch Huge Good Dick

If you don't already know me my name is Juan. Im athletic basketball player I love all sports. Interested, want some real entertainment get connected. Well traveled educated and connected. I've always been spoiled and my fetish is to be worshipped. I'm bilingual What are you waiting for? Contact me ... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (312) 320-9629Home+1 (312) 320-9629
Email
In Rate Out Rate
$300 $300

Chicago Mar 5th to 8th ONLY

Toned fit 5'9 165lbs BIG FAT 8.5x5 blue eyes brown hair. Gym 5 times per week. Clean drug and disease free. Mild to wild. Central location Ask to see my reviews.
travel adChicago, IL
My Phone Number
Mobile+1 (206) 549-9209
Email
In Rate Out Rate
ask me ask me

Massage By Eric

Come experience my art of healing... I am a Licensed Massage Therapist (LMT) and artist weaving the therapeutic and erotic, onto your body's canvas. I offer Swedish Full Body massage and Thai Yoga variations, which involves a floor matt and assisted stretching, compressions and acupressure with... (more)
I'm #7 on the map Chicago, IL
My Phone Number
Mobile+1 (612) 360-0162
Email
In Rate Out Rate
$120 $100

Irish lad in the big city! 7-17 through 7-24

A hundred years or more ago, thousands of Irish moved to New York City to fulfill their dreams of living in tenement housing in Brooklyn. Now, in the present, Jack Riley is bringing up the rear. Literally, so to speak. As an Irish immigrant, I bring a great experience to any appointment. I do have t... (more)
Chicago, IL
My Phone Number
Mobile+1 920-636-6957
Email
In Rate Out Rate
$200 $200

CHICAGO'S HAIRIEST GINGER

Hello, and thank you for checking out my profile. I am an affectionate individual and love body contact. I am also experienced with BDSM and fisting top. I have a wide range in interest from cuddling to watersports and all that inbetween. Friendly, discrete, educated art student. Contact me via text... (more)
I'm #8 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 574-0912
Email
In Rate Out Rate
$250 $200

DISCREET 24y/o hung TOP 9x6 Guaranteed Satisfaction Every Time

Hey guys Im logan, Im dom. top and bi. Im 5'9 athletic build spanish mix, masculine and extremly passionate and love to have a good time. I can go from mild to wild. I am hiv neg.  drug and diesease free. If there is something not listed in my profile ask and maybe something may be arranged. ca... (more)
Chicago, IL
My Phone Number
Mobile+1 (619) 549-6053
Email
In Rate Out Rate
$300 $300

Uncut Latin Jock

Hey, im Daniel. i'm a very open minded and well educated young man. My goal is that you enjoy yourself fully, without anxiety or hesitation, i enjoy exploring new things and creating meanful conecctions with people, If you are looking someone exiting, a guy that is easy going, super friendly wi... (more)
Chicago, IL
My Phone Number
Mobile+1 (773) 614-7645
Email
In Rate Out Rate
$250 $250

Shaun the freak

Hi guys new to escorting just unleashed my inner freak for generous males I'm very open to trying new and excited things I have an amazing 10 1/2 inch dick that seems to stay hard and ready I'm very discreet and  I'm into fulfilling fantasy's and being a partner as well  for companionship ... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (773) 557-6837Home(773) 557-6837
Email
In Rate Out Rate
Ask me Ask me

MUSCLE JOCK

Young muscular jock, very handsome, 6', 200lbs, bubble butt, versatile, moderately hairy. Friendly, outgoing, and laid back. Love to travel and enjoy longer sessions.Open to most scenes and i'm a expert cocksucker. Best way to reach me is to call or text me at 708-254-9622 please no private or bloc... (more)
Chicago, IL
My Phone Number
Mobile+1 708-254-9622
Email
In Rate Out Rate
$225 $225

Hot , Smooth , Clean , Discreet...

Are you looking for an amazing experience? Then you are at the right place. Hey guys. My name is Luis. Clean, toned, smooth, very discreet. I can come over to your hotel room or your own place. In Chicago or burbs. If you would like to come to me I can host too. Providing amazing full body massage. ... (more)
Chicago, IL
My Phone Number
Mobile+1 (630) 999-7741
Email
In Rate Out Rate
$160 $160

Hi,  I am an 18 year old student that just moved to Chicago attend DePaul next term.  I consider myself vers but I prefer to top. I tend to be more on the dominant side, but If you push the right buttons I can be submissive. I live in the Oak Park area but I am willing to travel. I am a co... (more)
Chicago, IL
My Phone Number
Mobile+1 (708) 710-2485
Email
In Rate Out Rate
Ask me $200

page of 5
in/out rate
in rateIn Rate
out rateOut Rate
star rating
rate from 1 to 5rate from 1 to 5
unratedunrated
Foreskin
cutCut
uncutUncut
Age
# of years# of years
Sexual Position
topTop
bottomBottom
versatileVersatile

signup for the rentboy.com newsletter

Don’t miss out on our latest news, events, and the sexiest men available near you!