Rentboy – Largest Gay Male Escort and Massage Site

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex





86 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.

FROM THE DARKNESS COMES YOUR LIGHT

First and formost I would like to thank the 3.5 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)
I'm #1 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 642-6402
Email
In Rate Out Rate
$250 $225

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)
I'm #2 on the map Chicago, IL
My Phone Number
Mobile+1 (404) 860-1213
Email
In Rate Out Rate
$225 $250

RENTBOY'S MR. LOS ANGELES IS VISITING CHICAGO APRIL 14TH - APRIL 19TH - (310) 721-9472

VISITING CHICAGO APRIL 14TH - APRIL 19TH What's your fantasy? Mike de Marko is Rentboy's Mr. Los Angeles 2015 as well as the winner of the Hookies award Best Boyfriend Fantasy!!!LA based XXX model - World Traveler - Lover of all things SoCal. College Educated - From camping to caviar, this RENTBO... (more)
I'm #3 on the map Chicago, IL
My Phone Number
Mobile+1 (310) 721-9472
Email
In Rate Out Rate
$300 $300

Enjoy

Let me know what you have in mindtext/email preferred  
I'm #4 on the map travel adChicago, IL
My Phone Number
Mobile+1 (312) 854-9204
Email
In Rate Out Rate
Ask $180/hr, 300/2hrs

Passionate and intimate encounter!!

 Hot muscular porn superstar. Working in the adult industry COLT,FALCN,RAGING STALLION ,HOT HOUSE Entertainment. Passionate, fun to be around, and I sure know how to have a good time. (Safe Only) . Lets live your Fantasy's together.I will only be in LA for a Brief Moment Text or Call to set som... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (917) 513-2027
Email
In Rate Out Rate
$150 $150

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 #5 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

I am the best .No worries 100% real

 TRUE   experience for the right person  , also with alot more pics to share upon request, im very athletic and my ad is real and my motives are to have fun  !!  ,I  provide a vast array of options such as personal training or martial arts, domination, wrestling with st... (more)
I'm #6 on the map Chicago, IL
My Phone Number
Mobile+1 3128591581
Email
In Rate Out Rate
Ask me asm me

South Florida Bound MONTH OF FEBRUARY

Hey guys my name is Mike. I am the muscle man of your dreams. I’m 28 years old, 5’11’’, 170 pounds (of pure ripped muscles) and 7% Bodyfat, 30in Waist, 8.5" UNCUT and GIRTHY, HIV NEG and DDF. Smooth ski, mix of Greek, Spanish and Italian. My pics are very recent and 100 perfe... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (772) 452-7768
Email
In Rate Out Rate
$150 $150

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

Skilled, Professional, focused on you

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
$240 $260

Here to please

Here until June 26th. Moving to Denver and trying to save for that move. If you're looking for a fun and intimate friend, I'm your man.  My name is Brian and I'm 26. In school for real estate and real estate law. I'm a pretty open minded guy :)  please contact me via my email. brianbrody2... (more)
Chicago, IL
My Phone Number
Email
In Rate Out Rate
Ask me $250

Stop searching the rest, you've just found the best!

Sexy, intelligent, playful.... Fresh off the farm and well traveled. You can't get any better than that! Romp in the sack? Night on the town? Whats your flavor? Providing an array of experiences and all you have to do is message me and the rest will follow.experienced in erotic massag... (more)
I'm #7 on the map Chicago, IL
My Phone Number
Mobile+1 (312) 967-9612
Email
In Rate Out Rate
Not preferred $200

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

Available for travel

I am a well traveled guy that has been around the globe a few times already.  Speak French and English fluently.Big hairy hockey legs, 8" uncut thick dick and muscular built.  Versatile top.Passionnate, affectionate and adventurous.  I fulfill perfectly the typical "boyfriend fantasy"... (more)
Chicago, IL
My Phone Number
Mobile+1 (250) 706-9096
Email
In Rate Out Rate
$220 $250

European Hung Jock visiting Chicago April 22-25

Hello, my name is Aidan. I am a former college athlete, open to most things as long as safe and clean. I respect and value my clients and expect the same in return. Also, I appreciate a brief introduction of the person and his interests in the initial contact, this way I can make sure that I am able... (more)
I'm #8 on the map travel adChicago, IL
My Phone Number
Mobile+1 (646) 535-4561
Email
In Rate Out Rate
$260 $300

Passion, Pleasure, and Endurance. Experience the difference.

Passionate, Aggressive, Sexy, and hung athlete with massive pipe and stroke game. Available for in and out calls. Specialties include massage, intimate dates, and passionate aggressive love making. All pics are real. And I aim to please. Call 267 225 0671- Jaylon
travel adChicago, IL
My Phone Number
Mobile+1 (267) 225-0671
Email
In Rate Out Rate
Ask me Ask me

Actively Looking
25 Top Cut

12in BIG DICK BOSS HOSTING LAKEVIEW

I AM THE COMPLETE PACKAGE IF YOU SEE SOMETHING YOU LIKE CALL TXT ME NOW YOU WILL NOT BE DISAPPOINTED. I LOVE WHAT I DO, AND YOU WILL LOVE HAVING ME :) DEVONSTARR 100% TOP DOWN TO EARTH AND LEVEL HEADED. MILD TO WILD, YOUR CALL. MUSCULAR, LEAN, 24Y/O CLEAN CUT WELL GROOMED, KIND AND GENTLE AS YOU CO... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (773) 628-3772
Email
In Rate Out Rate
$150HR 250/2hrs 300/3hrs $200+

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

HUNG STUD(10x6") AVAILABLE FOR YOU-LIMITED TIME

HI ALEX HERE -THANKS FOR CHECKING OUT MY  AD - VISITING CHICAGO - LIMITED TIME. GREAT LOOP LOCATION.Hi - This FRIENDLY sexy masculine hung guy would love to fulfill your pleasures and needs.Naturally smooth skin ,nicely muscled-v-shaped torso and amply hung -a hot 10x6" thick cock.Talented ver... (more)
I'm #10 on the map Chicago, IL
My Phone Number
Mobile+1 (917) 421-6353Home+1 (917) 421-6353
Email
In Rate Out Rate
$250 $300

YONG & FRESH SEXY LATINO

HEY GUYS WHAT SUP IM OLIVER A GOOD LOOKING LATINO GUY IM VERY FRIENDLY AND VERY CLEAN...IM 5"8 TALL 148 LBS...NICE THICK 8" UCUT , NICE BUBBLE BUTT LEAN BODY AND ALWAYS READY TO GIVE U A GOOD TIME IM 100% REAL SO IF U ARE LOOKING FOR A GOOD TIME JUST TRY ME AND U GONNA LIKE ME THE BEST WAY TO CONTAC... (more)
travel adChicago, IL
My Phone Number
Mobile+1 323 481 8671
Email
In Rate Out Rate
Ask me Ask me

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 te... (more)
I'm #11 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 574-0912
Email
In Rate Out Rate
$250 $200

All night luva

If you're looking for a handsome face, a sexy build you've found it!!! Have an unforgettable experience with a young, sexy dude seeking to please you, whether through a sensual massage, or being your company through the night which you"re sure to have the best time of your life!! Whatever you decide... (more)
Chicago, IL
My Phone Number
Mobile+1 7735677170
Email
In Rate Out Rate
Ask me Ask me

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!