Rentboy – Largest Gay Male Escort and Massage Site
Find Boys...

Advanced Search »

filters

You can use these checkboxes to limit your results. Check the characteristics that you like. Have fun!

Sexual Position




Foreskin



Age Range


In Rate


Out Rate


Cock Size


Ethnicity











Tastes / Specialties / Fetishes




















Body Hair






Build








Safe Sex




101 male escorts and male masseurs In Chicago, Illinois

switch view map card thumbnail realtime
stat card
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.

Why play with the rest when you can be with the Best

Hey Guys! Whether you're looking for a Hot and Fun time or a just a Companion to go to with to a black and tie dinner, let me be the one to fulfill them both. I'm a very social, fun, and outgoing individual that is educated and well mannered. I play a lot of sports here so if you're looking for a pl... (more)
Chicago, IL
My Phone Number
Mobile+1 (561) 713-6174
Email
In Rate Out Rate
$300 $300

SomeAssTime

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 Por... (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

Hookies Mr. Chicago 2014, Traveling to Toronto Pride Late June

Furry muscle guy here to provide excellent companionship. I enjoy dinner dates, cuddling, hitting the town, or just staying in bed all weekend long. You’ll find me natural and confident top, professional, educated and very into what I do. I’m 27, 5’11, 207 lbs, brown hair, hazel e... (more)
Chicago, IL
My Phone Number
Mobile+1 (872) 216-1618
Email
In Rate Out Rate
Ask me $300

Actively Looking
24 Top Cut

...

prefer email, then text.
Click to open map travel adChicago, IL
My Phone Number
Mobile+1 (312) 854-9204
Email
In Rate Out Rate
Ask me $180/hr

Actively Looking
27 Versatile Cut

I Swallow

Hello all. I am a very handsome Middle Eastern guy. I am 27, 6'3'' 200 pounds, hairy. An expert cocksucker (who always swallows) and rimmer as well as a tight, muscled-ass bottom, I am genuinely into physical contact with other men. I love sex more than anything else. Absolutely not a clock watcher.... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (646) 732-2360
Email
In Rate Out Rate
$150 $180

Do you like the Cuban Spice?

College boy, very good kisser ,very passionate,and very down to earth, very educated and available for hourly overnight, weekend and traveling , please call or text , emails are forever nowdays.
Chicago, IL
My Phone Number
Mobile+1 (630) 639-3614
Email
In Rate Out Rate
$200 $300

Good vibes here , CLEAN , Dominant TOP

hello I'm a masculine, discreet,  good looking guy that is here for a mutual beneficial  TRUE experience .  I prefer to go out for dinner or any cuasul date to get to know you first , don't have to though , also dont hesitate to ask me to visit you if your out of state , I love travel... (more)
I'm #4 on the map Chicago, IL
My Phone Number
Mobile+1 3128591581
Email
In Rate Out Rate
Ask me asm me

Available in Chicago til Aug 4 & Return Aug 22

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

Actively Looking
24 Versatile Uncut

Hot European guy with classy look

Let's keep it simple: If you're looking for a hot, hung, fun, guy, I am your guy.  I enjoy working out, travelling or just hanging out. Whether you are just looking for an hour, overnight or a weekend, you will enjoy our time together   Services are by the hour or preferably a long t... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (773) 580-5245
Email
In Rate Out Rate
please ask please ask

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

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

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$200.00 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

Actively Looking
32 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.
Click to open map Chicago, IL
My Phone Number
Mobile+1 (312) 905-4691
Email
In Rate Out Rate
Ask me Varies

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
Ask me $250

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 decid... (more)
Chicago, IL
My Phone Number
Mobile+1 7735677170
Email
In Rate Out Rate
Ask me Ask me

Pleasure and Passion at your knees Chicago mate

I'm a down to earth professional escort, very sweet and passionate with a great personality skilled 7.5" versatile stud great kisser amazing top and bottom fit with a great body also a tattooed stud but don't let it fool you very well educated with a lot of Latin passion. Please no private calls or ... (more)
I'm #8 on the map Chicago, IL
My Phone Number
Mobile+1 (847)644-9874Home847-749-8541
Email
In Rate Out Rate
Ask me $250

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

Actively Looking
31 Top Uncut

100% Texas Beef!

31 yr. old Latin male, 5'8, 31" waist, 156 lbs. Discreet, respectful, easy going, open minded, adventurous, spontaneous, and most importantly, I play well with others :) Please feel free to contact me at anytime on my cell or by text.  Here is the link to "Another Morning" ENJOY!  ht... (more)
Click to open map travel adChicago, IL
My Phone Number
Mobile+1 773-236-0126
Email
In Rate Out Rate
Ask Me $200

Young, athletic model for massage and more

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

Brown, Hard and ready! 11 inch Hershey Bar!

How goes it fellas? I'm A smooth college kid with a Thuggish swag. I'm masculine but gentle. I'm a young man trying manage school and keeping a roof over my head. I'm a top. Text,email or call. No hassle for the time of your life! Excellent Massages! Great Hands!Very affectionate guy here. I also ca... (more)
travel adChicago, IL
My Phone Number
Mobile+1 7087379133
Email
In Rate Out Rate
ask ask

Masculine Body Builder

Easygoing and super friendly muscle man. I'm kind of like my dog...I might look like I'm going to bite, but I just want to lick you! I like to kiss and I'm very affectionate. Educated, easy to talk to and good dinner company. Very versatile, can be sweet and playful or kinky and twisted! Really enjo... (more)
I'm #10 on the map Chicago, IL
My Phone Number
Mobile+1 312-391-4541
Email
In Rate Out Rate
$225

Hot and Ready.

Seems like Every City can be called Home. Back on here after a Long Relaxing Vacation. Ready to meet more greatest peoples and make your dreams Come true . If we haven't meet yet, I will be happy to meet you and relax all that stress there is been caused by Been horny . Less Stress... Let's not wast... (more)
I'm #11 on the map Chicago, IL
My Phone Number
Mobile+1 (312) 560-3223
Email
In Rate Out Rate
$130 $130

stat card
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