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 masseurs In Chicago, Illinois

card grid realtime
page of 5
Actively Looking
39 Cut

Time to Fall Back into These Arms

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)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (773) 354-8802
Email
In Rate Out Rate
$225.00 $250.00

Actively Looking
32 Versatile Cut

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) 905-4691
Email
In Rate Out Rate
Ask me Varies

MARCHELLO HOT LATINO in CHICAGO BOOKING NOW 100%DESCRETE/ PICS

BEST WAY TO GET A HOLD OF ME RIGHT AWAY BY CALLING OR TEXT ME, Chicago escort/very good looking LATIN VERY FRIENDLY ESYGOIN LIKE TO KISS ORAL MAKING LOVE, FREE ACTITUD , . 26/5'11" 175 /muscular buff/natural smooth all over/ AVAILABLE FOR ALL AGES AND SHAPES , LIKE OLDERS GUYS, IAM FREE OF STD HIV, ... (more)
Chicago, IL
My Phone Number
Mobile+1 312-375-6020
Email
In Rate Out Rate
$180$ Ask

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 return to ... (more)
I'm #2 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 870-2154
Email
In Rate Out Rate
$225/hr $250/hr

In Chicago Friday 11/28- Sunday 11/30

Hey    Looking to have some fun tonight or interested in booking for the future?   I'm available for 1 on 1 privates, dinners, muscle worshipping, fetishes, shopping sprees, or if you just want someone to spend time and talk too.   I come discreet and ready to have some fun... (more)
Chicago, IL
My Phone Number
Mobile(352) 346-0181
Email
In Rate Out Rate
$140 $160

Bigger is always better

COME experience a session that will blow your mine!!! I specialize in 1st timers , which I aim to make your 1st experience a very pleasurable one, Massages, Role-Play, Mild-to-Wild, Domination, Companionship, Private Sessions, etc Certified Massage therapist!!! If you want to have one of the best se... (more)
Chicago, IL
My Phone Number
Mobile+1 (630) 917-1884
Email
In Rate Out Rate
$250 $300-400

Latin Twink

Very smart and great personality make for amazing company.  Enjoy a good bottle of wine, dinner, going out for drinks, and exploring the city and traveling.  Let me know what you are interested in and we will go from there.
I'm #3 on the map Chicago, IL
My Phone Number
Mobile(951) 331-8137
Email
In Rate Out Rate
Ask me $180

Actively Looking
31 Versatile Cut

Insatiable Muscled Jock-Make your Reservations NOW!!! 4 Days ONLY!!! Dec 4th to Dec 8th (303) 359-3192 WWW.ELIDANIELSENTERTAINMENTNETWORK.COM

***CHICAGO AREA for 4 DAYS ONLY 12/04 - 12/08 & 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... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (303) 359-3192
Email
In Rate Out Rate
$300 CASH or CREDIT $350 CASH or CREDIT

Masculine Sexy Top

Sexy,  fun &  well endowed, masculine top. I'm mature,  confident, and always professional. I always deliver, never under perform. I can be your passionate boyfriend or a dominant and aggressive pig. I get into most every scene, I love to party. I've got a thick and meaty 7.5 inch... (more)
I'm #5 on the map Chicago, IL
My Phone Number
Mobile+1 (310) 927-9484Home+1 3109279484
Email
In Rate Out Rate
$250 $250

12IN HOSTING IN MY OWN LAKEVIEW APARTMENT $100 SPECIAL OR I DRIVE

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)
I'm #6 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 628-3772
Email
In Rate Out Rate
$150ASK 100SPECIAL $200ASK 150 SPECIAL

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 #7 on the map Chicago, IL
My Phone Number
Mobile+1 773-413-8086
Email
In Rate Out Rate
$225.00 $250.00

Irish lad - funny, fit and free-spirited

Thanks for looking at my ad! I'm an Irish lad here in Chicago, available for incall and outcall (prefer outcall). I'm known for being the type of man who will make you laugh, show you the best of Chicago. Whether it's a dinner, evening's entertainment, a night of conversation and passion, or a trip... (more)
Chicago, IL
My Phone Number
Mobile+1 (708) 600-6754
Email
In Rate Out Rate
$200 $200

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

Smart/Handsome/College/Boy @ your Service.

Smart intelligent College Boy At your Service. Never looking at the Clock and always Ready to Release that Stress and Make you feel better after a long Day. Very mature and friendly always like new adventures. Seems like every City can be called Home and I get to stay Longer when I'm having that war... (more)
I'm #8 on the map Chicago, IL
My Phone Number
Mobile(312) 560-3223
Email
In Rate Out Rate
$130 $130

When You're Ready, Come And Get It! (773) - 426 -1145

HEY WHATS UP! ?My Name Is Diego, I'm a Very Clean, Cool and Good Looking Latin Guy.I'm 22 Years Old, 5'3ft 130lbs 7in Cut, Vers.I'm Very Open Minded and Willing tO Try Fetish's Fantasies Etc.Never Feel Shy, NervOus or Unsafe. SatisfactiOn is Always Guaranteed.First Timers and Older Guys are Always W... (more)
Chicago, IL
My Phone Number
Mobile+1 (773) 426-1145Home7724261145
Email
In Rate Out Rate
$200 $250

Want to turn up the heat?

Hot, masculine and discreet! Sexy European, well educated, fun, sensitive with a wild side available for some sensual fun. Looking for a relaxing and erotic massage (and more), companionship, fetishes and/or sexual play? I can make your fantasies a reality. I can take it slow for first-timers and th... (more)
Chicago, IL
My Phone Number
Mobile+1 815 919 7804
Email
In Rate Out Rate
$200 $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

THE TOTAL PACKAGE

Hot Masculine Top Guy 6 ft 178 32w 42c Clean and safe very discreet educated and professional guy,I'm a very outgoing with no attitude genuine guy.Reliable and honest.I'm very clean and safe a great companion for those guys that appreciate good company as well as good times! I enjoy the theater, mov... (more)
Chicago, IL
My Phone Number
Mobile(312) 285-6821
Email
In Rate Out Rate
$175 $200

I can keep you warm ;)

Hey! My name is Riley.  I am friendly, kind, fun, athletic and love to have fun. I only play safe and up for almost anything. I can accommodate you and For sure keep you warm ;)
Chicago, IL
My Phone Number
Home+1 (312) 576-6901Home+1 (312) 576-6901
Email
In Rate Out Rate
ask me ask me

Versatile Midwestern Bubble Butt Porn Dude Visiting

Lets have some fun while I'm visiting!  Check out some of my porns there and there.  And no, I'm not a total PowerBottom!  I just play one in the movies!  Of course some of the best tops are bottoms.  I am mild to wild kinky or vanilla and very well experienced in fisting...... (more)
Chicago, IL
My Phone Number
Mobile+1 (402) 871-6928
Email
In Rate Out Rate
$200 $240

Natural, Athletic, Discreet

Discrete guy here. Drama free and always on time. Awesome cocksucker! I am interested to please and also can go any where from mild to wild for an enjoyable man on man interaction. I'm cool with working with couples or other escorts. Party's are fun. I aim to please. Can be dom or sub. I'm versatile... (more)
Chicago, IL
My Phone Number
Mobile+1 (312) 343-9348
Email
In Rate Out Rate
$200 $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!