Rentboy – Largest Gay Male Escort and Massage Site

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex





92 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.

Actively Looking
27 Versatile Cut

Southern Hospitality,

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)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (404) 860-1213
Email
In Rate Out Rate
$200 $220

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

Warm up :D

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

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

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 #3 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 #4 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 870-2154
Email
In Rate Out Rate
$225/hr $250/hr

Aggressive, Passionate, and Discreet.

If an Authentic Experience is what you're wanting, you don't need to look much further . . . I honestly dig what I do. I have a lot of fun with it, and I know what i'm doing. I'm New, and I'm Honest. Real Age, Real Photo. Clean Guaranteed! Feel free to call or text w/ any further questions.
Chicago, IL
My Phone Number
Mobile+1 (312) 483-7976
Email
In Rate Out Rate
Ask me Varies

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

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 #5 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 #6 on the map Chicago, IL
My Phone Number
Mobile+1 (312) 647-6567
Email
In Rate Out Rate
$210 $230

Total Satisfaction

Sexy, Fun, and Well-Endowed, Masculine Top... Im easy to be around, have a sense of humor and alays alow things to play out at your comfort level. I'd say that Maturity Confidence, Professionalism and a love for fun define me. If you're looking for two guys I work with several really hot men th... (more)
Chicago, IL
My Phone Number
Mobile+1 (310) 927-9484Home+1 3109279484
Email
In Rate Out Rate
Ask me for details $250

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 #7 on the map travel adChicago, IL
My Phone Number
Mobile+1 321-287-4568
Email
In Rate Out Rate
$250 $300

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

Actively Looking
28 Top Cut

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

Actively Looking
29 Top Cut

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

GENUINE & PASSIONATE - IN TOWN MARCH 19-23 ONLY!

Hi! My name's A.J. I'm, 5'6", 145-150lbs., athletic/muscular build. Ripped, tight and smooth body, hairy legs (below knee), 6.5" thick cut cock, low hanging balls and In great shape...I have black hair, brown eyes, tan & soft smooth skin, clean cut, masculine, and from what some have said a pret... (more)
Chicago, IL
My Phone Number
Mobile+1 (714) 743-5652
Email
In Rate Out Rate
$250 $300

Sexy, young male escort in Chicagoland area 815-277-9678 MONSTERSCOOP27@OUTLOOK.COM

Hey Fellas!My names Blake, nice to meet you. I'm a friendly, sexy, college student that enjoys meeting new people and having a great time in the greatest city in the world!I am 22 years old, 5'11'', 165lbs, athletic with a nice thick nearly 8 inch cock thats always down for action. When I'... (more)
travel adChicago, IL
My Phone Number
Email
In Rate Out Rate
Ask me $175

Actively Looking
22 Top Cut

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

Young, intelligent, athletic model for good times in Chicago and beyond

I'm a young, fun, intelligent, sexy model working as an escort to help pay my way through school. I've been an athlete my whole life and my body shows it. I'm well-cultured and traveled, able to hold a meaningful conversation, and a lot of fun to be around. I'm very adaptable to any situation, and a... (more)
Chicago, IL
My Phone Number
Mobile+1 (831) 512-9356
Email
In Rate Out Rate
Outcall only $200

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

I ARRIVE IN CHICAGO FRIDAY AFTERNOON AND LEAVE MONDAY. call to schedule an appointment. 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 fre... (more)
Chicago, IL
My Phone Number
Mobile+1 (619) 549-6053
Email
In Rate Out Rate
$300 $300

Just landed here in NEW YORK! New hung meat on the shelf for you! - 22

New to your Big city, but I'm a big guy so I think I'll fit in just fine! I'm 6'2 190lbs.I'm 12 inches hung and extremely handsome. Everyone says they're dominant, but are they really? Well I'm the real deal hit me up for a great time with a masculine guy.3129614795
travel adChicago, IL
My Phone Number
Mobile+1 (847) 971-2286
Email
In Rate Out Rate
Ask me Ask me

Actively Looking
29 Versatile Cut

I'LL BE UR EROTIC MASSEUR / FUN TIME!

Are you looking for someone exciting to deliver a mind-blowing, toe-curling experience? A guy that's easy going, super friendly & FUN, who will give you a perfect & passionate EROTIC MASSAGE experience...or that nasty, HOT & WILD time you've fantasized about? You've found your boy! We'r... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (312) 560-3223
Email
In Rate Out Rate
$150 $150

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!