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

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.

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)
I'm #1 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 354-8802
Email
In Rate Out Rate
$225.00 $250.00

Fun guy next door!

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 #2 on the map Chicago, IL
My Phone Number
Mobile+1 (312) 725-0690
Email
In Rate Out Rate
$250 $300

Actively Looking
25 Versatile Uncut

Hi everyone! My name is Tony you typical Cuban lover, very passionate, laid-back, nice, educated guy.I'm also very discrete,and respectful and a little shy.If you are looking for a nice relaxing time or just a nice company for a dinner etc..i'm your guy.  Hope to hear from you soon and please o... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (630) 639-3614
Email
In Rate Out Rate
Ask me200 $350

Chicago October 17th- 22nd O'Hare airport

Hello Boys, All american boy, Clean Cut, healthy and a passion for pleasing other's. I am your ultimate Fantasy and boyfriend come true. I am passionate, confident, masculine behaviour with a submissive side and very good at being discreet. I am excellent at conversation, massage, and other companio... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (207) 812-1795
Email
In Rate Out Rate
$220 $300

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)
travel adChicago, IL
My Phone Number
Mobile+1 312-375-6020
Email
In Rate Out Rate
$180$ Ask

Midwestern Bubble Butt *PORNSTAR*

Lets have some fun!  100% Discretion assured!  100% Versatile here :)I can host or travel with ease…  Private Gallery Password is:  enter  Companionship and conversation are a no brainer for me - whether its cocktails and dinner you'd like, you just need some man to m... (more)
Chicago, IL
My Phone Number
Mobile+1 (402) 871-6928
Email
In Rate Out Rate
$220 $260

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

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

Visiting Chicago 10/17-10/20! Sexy, Mischevious & Versatile Jock Next Door - BFE & Overnight Specialist ;)

**VISITING CHICAGO 10/17-10/20 - PLEASE EMAIL** **PASSWORD TO LOCKED GALLERY IS "andrew"** My name is Andrew and I was born and raised in France, but attended American schools for the most of my life. I have traveled extensively around the world and enjoy learning about new cultures, especially sinc... (more)
Chicago, IL
My Phone Number
Email
In Rate Out Rate
$250/1hr,$400/2hrs, $500/3hrs $300/1hr,$500/2hrs, $600/3hrs

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

Visiting Chicago ***206-319-8610*** Oct 28- Nov 10th

In Chicago Oct 28th! Advanced notice is greatly appreciated.  TRAVEL DATES -  San Diego Oct 5th- 20th L.A. Oct 20th - 28th Chicago  Oct 28th - Nov 10th  Handsome and Muscular Stud. I’m 5’10 ft. 180 lbs of solid proportionate muscle (Work outs/Gymnastics... (more)
Chicago, IL
My Phone Number
Mobile+1 (206) 319-8610
Email
In Rate Out Rate
Ask me Ask me

Eastern European Experience

Honest gentleman 26 yo Eastern European stud that everyone describes as a sweetheart. bad boy body, Great kisser, skilled 8" top - amazing bottom. I love to make people happy. Friendly and professional with perfect hygiene. Picture are recent and genuine. Text me (no emails) - no blocked numbers.
Chicago, IL
My Phone Number
Mobile+1 530-936-7883
Email
In Rate Out Rate
$250 $250

PIG in a Blanket- Make your Reservations NOW!!! 3 Days ONLY!!! OCT 17th to 19th (303) 359-3192 WWW.ELIDANIELSENTERTAINMENTNETWORK.COM

***Currently Serving Denver Area but will be in the Chicago area for 3 days ONLY 9/17 - 9/19 & 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 camer... (more)
Chicago, IL
My Phone Number
Mobile+1 (303) 359-3192
Email
In Rate Out Rate
$300 CASH or CREDIT $350 CASH or CREDIT

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

HI ALEX HERE -THANKS FOR CHECKING OUT MY  AD- VISITING CHICAGO -LIMITED TIME.GREAT DOWN TOWN   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" th... (more)
I'm #6 on the map Chicago, IL
My Phone Number
Mobile+1 (917) 421-6353Home+1 (917) 421-6353
Email
In Rate Out Rate
$250 $300

Young. Energetic. Educated. Eternally Curious.

Hi Gentlemen -Firstly, allow me so say thank you for visiting my profile. I'm a young, enthusiastic, intelligent, witty, and handsome guy looking for memorable experiences both in and out of the bedroom. Great conversationalist with a flair for social settings. I clean up well, and look great i... (more)
Chicago, IL
My Phone Number
Mobile+1 (815) 483-9886
Email
In Rate Out Rate
Ask me Ask Me

Visiting Chicago area 10/17 - 10/20

Hey Guys, thanks for checking out my ad. Visiting the Chicago metro area Oct. 17th - 20th....I'm 5'11", 187 lbs, 32"w. Very Friendly easy going guy with no attitude. Discreet, Safe, Tan, Masculine, Muscular, and been told Im handsome ;-). Hung thick, true 8.5x6 uc and a great bubble butt. Open ... (more)
travel adChicago, IL
My Phone Number
Mobile+1 407-810-3607
Email
In Rate Out Rate
$250.00 $250.00

Ambitious, friendly, sexy boy.

Hey guys, my name's Evan. I'm a fun, smart, young guy visiting Chicago from 10/21-10/25. I'm extroverted, outgoing, well-spoken, and educated. I'm very easy to talk to and great company. What you see is what you get here, and I'm pretty amazing just being me. I have extremely varied interests in an... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (202) 643-4560
Email
In Rate Out Rate
$250 $250(DC) 300(metro area)

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

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

Southern Fried sexy

° Georgia born and bred, I am new to the big city of Chicago. Bringing my southern charm to ChiTown M4M experience, I will show you a new level of relaxation and sensuality from one man to another. I love my men, their bodies and the release that time under the care of my masculine hands br... (more)
Chicago, IL
My Phone Number
Mobile+1 (615) 306-2711
Email
In Rate Out Rate
Ask me Ask me

Massage By Eric

Come experience my art... I am an artist specializing in the body, on canvas and the tapestry of the skin. I offer Swedish Full Body massage and Thai Yoga variations, which involves a floor matt and assisted stretching, compressions and acupressure. Combinations thereof are curtailed to your individ... (more)
Chicago, IL
My Phone Number
Mobile+1 (612) 360-0162
Email
In Rate Out Rate
$100 $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!