Rentboy – Largest Gay Male Escort and Massage Site

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex





91 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.

Clay is your man!

Hey guys, I'm a fun, sensual guy. I really enjoy to sucking cock and like to kiss! Versatile when it comes to fucking. I enjoy pleasing a man! Let me fulfil your fantasies and desires! Send me a text or email! Look forward to hearing from you!
I'm #1 on the map Chicago, IL
My Phone Number
+1 (312) 725-0690
Email
In Rate Out Rate
$225 $250

Im here to make you feel like you have never felt before

Passwoaller
Chicago, IL
My Phone Number
Email
In Rate Out Rate
$200/hr $150/hr

Established Male Geisha: mild 2 wild

 Turkey:  4/18th - 5/10. Seattle 5/10 - 14. Milwaukee/chicago: 5/19 - 5/31. Raleigh: 6/1 - 10th. U.S. / international companion w/ excellent reviews~ (15 yrs experience). Responsible, stable, dependable. Happy go lucky/horny as the day/night is long~ Multiple cummer for overnights & lo... (more)
Chicago, IL
My Phone Number
+1 (971) 400-2633
Email
In Rate Out Rate
$2hrs=$350, 3hrs=$500, 6hrs=$600 $2hrs=$350, 3hrs=$500, 6hr=$600

Actively Looking
35 Versatile Cut

Miracle Mile hotel Chicago IN/OUT calls(646)315-1823

Are you looking for a passionate, discreet, reliable, sensual and handsome guy in Chicago? You've found him! I'm available for men like you who desire a high-quality experience. I can host in my private and conveniently located downtown hotel, or I can travel to you. I can take complete control, or ... (more)
Click to open map travel adChicago, IL
My Phone Number
+1 646-315-1823
Email
In Rate Out Rate
$250 + CC accepted $250 + CC accepted

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
+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
+1 (312) 483-7976
Email
In Rate Out Rate
Ask me Varies

Actively Looking
28 Top Cut

Visiting Chicago May 1-5

Im currently living in San Diego and Ex Military going to school part time and training for triathlon. I have impeccable hygiene,masculine and 7.5 thick Latin dick. I have a wide range of tastes so If looking for boyfriend experience or something more on the wild side I specialize in different kink ... (more)
travel adChicago, IL
My Phone Number
+1 (619) 346-5301
Email
In Rate Out Rate
$250 $300

FITNESS MODEL 6'3 ripped, 20'' ARMS, & VERY HUNG

Hey there! Your muscle fantasy is ME. My stats are 6'3 225 pounds of pure ripped muscle. My two most impressive muscles are my 20 inch arms and beautiful Pecs. However, don't let my intimidating figure scare you :) My personality ,SMILE, and all around character is what I'm most proud about. Of cour... (more)
I'm #4 on the map Chicago, IL
My Phone Number
+1 (773) 829-5582
Email
In Rate Out Rate
$250/hour $250/hour

Smart, Fit, Sexy

Hi, In me you get a sexy, intelligent person, who is passionate and thoughtful. I make great company for everything from dinner and cocktails to a night on the town or just getting cozy at home. I have an eclectic set of interests and am always excited to experience new things and enjoy traveli... (more)
Chicago, IL
My Phone Number
+1 (872) 215-2258
Email
In Rate Out Rate
N/A $200

Amazing massage by great hands.

Are you looking for an amazing massage 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. Providing amazing full body massage. I don't have a table, just your bed, but... (more)
Chicago, IL
My Phone Number
+1 (630) 999-7741
Email
In Rate Out Rate
$160 $160

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
+1 708-254-9622
Email
In Rate Out Rate
$225 $225

What your heart desires

Hey, Is  Rafaello Dias  and I am visiting Chicago I am 5'9" latino very handsome and nice guy.None of my picture are fake 100% Me. I have a lot of expierence and know how to satisfy. MY TIME  in town is limited so catch me while you can! The time we spend together is al... (more)
Chicago, IL
My Phone Number
+1 (630) 770-0935
Email
In Rate Out Rate
Ask me Ask me

  Laid back, confident, very good looking. Over all great guy. Gym 5x a week. 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. Feel free to contact me, I don't bit... (more)
I'm #5 on the map Chicago, IL
My Phone Number
+1 (404) 860-1213
Email
In Rate Out Rate
$225 $250

Actively Looking
23 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)
Chicago, IL
My Phone Number
+1 (773) 647-5940
Email
In Rate Out Rate
Ask me Ask me

Irish lad in the big city

A hundred years or more ago, thousands of Irish moved to Chicago to fulfill their dreams of living in tenement housing. 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 the sexy accent, as... (more)
Chicago, IL
My Phone Number
+1 (708) 600-6754
Email
In Rate Out Rate
$200 $200

Sicilian Boy

Hey there, my name is Giovonni. I'm a Horny young man who loves to have a good time. Completely versatile. I enjoy being challenged, traveling, and an impressive sweet red wine. Give me a call anytime, I'm a complete gentlemen.
I'm #6 on the map Chicago, IL
My Phone Number
+1 (708) 710-2485
Email
In Rate Out Rate
Ask me Ask me

Actively Looking
- Versatile Cut

HUNG STUD(10x6") AVAILABLE FOR YOU-VISITING

HI ALEX HERE -THANKS FOR CHECKING OUT MY  AD - VISITING CHICAGO -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 versatile top - do... (more)
Click to open map Chicago, IL
My Phone Number
+1 (917) 421-6353
Email
In Rate Out Rate
$250 $300

Actively Looking
31 Versatile Cut

Midwestern Muscle in Chicago

*Friendly-Adventurous-Passionate-Goofy-Masculine-Smooth*  I'm a fun-loving and outgoing guy who appreciates good conversation as well as charismatic sex appeal.  I get into a variety of scenes that can range from vanilla and sensual to wild and erotic.  Tell me any and all of your fa... (more)
Click to open map travel adChicago, IL
My Phone Number
+1 (347) 201-0309
Email
In Rate Out Rate
$250 $300

Young, Intellegent, Versatile, Seen in Chicagoland's #1 Prime Locations

If you are looking for a young, handsome, unforgettable guy, look no further.I offer exceptional, individual, opportunities, respectful of your interests. Have a discreet location to host in the suburbs or will travel within city limits.Compatable personality, adaptable to a wide range of characteri... (more)
Chicago, IL
My Phone Number
+1 (630) 795-9969
Email
In Rate Out Rate
$200USD $250USD

Actively Looking
24 Versatile Cut

Enjoy

Let me know what you have in mindtext/email preferred  
Click to open map travel adChicago, IL
My Phone Number
+1 (312) 854-9204
Email
In Rate Out Rate
Ask $180/hr, 300/2hrs

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
+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!