Rentboy – Largest Gay Male Escort and Massage Site

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex





115 male escorts and male massage therapists In Chicago, Illinois

card grid realtime
page of 6

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

For Those Whom Appreciate Customer Satasfaction

  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 porn talent, ... (more)
I'm #2 on the map Chicago, IL
My Phone Number
+1 (773) 642-6402
Email
In Rate Out Rate
$250 $250

Actively Looking
25 Top Cut

10in Dominican Papi XL

STEP INTO MY WORLD! Felipe Here; Sexy & Charming, Athletic, And Intriguing, I'm The Hung College Bi Jock Top, Here to Fulfill  Your Deepest Fantasies...Specialized In Domination w/, BDSM, Boyfriend Experience, Pig Bottoms, Fisting & Body Worship!...Felipe is VERY Masculine, Athletic, w/... (more)
Click to open map Chicago, IL
My Phone Number
+1 (774) 334-1025
Email
In Rate Out Rate
$275 $350

FOR SALE BY OWNER.

Hey there, my name is Kapov , 39 years , 6'0" my dick is 8 inches(not less). I live in  E LAKE VIEW - CHICAGO where I can have you in my private apt. Your pleasure is my pleasure and my goal. Always assertive, passionate and TOP / Versatile. I'm open to most scenes , let me know what's your fan... (more)
I'm #4 on the map Chicago, IL
My Phone Number
+1 (773) 891-8532
Email
In Rate Out Rate
$250.00 CREDIT CARD OR CASH $270.00 CREDIT CARD OR CASH

Established Male Geisha: mild 2 wild

SF: 6/16-17 & 28th-7/2... Seattle & Portland 7/3-18th. Possible travel to NYC, DC, MN and IN during that time at the beginning of July or end of if and early august~ U.S. / international companion w/ excellent reviews~ (15 yrs experience). Responsible, stable, dependable. Happy go lucky/horn... (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

Furry Young Man

Hi, I'm Clark! Back in Chicago Young, sensual, and all man. Totally versatile and looking to have some fun with you! Fluent in three languages and friendly in all of them.   I respect your requirement for discretion while I tend to your more intimate needs. Professional, intelligent, sexy, a... (more)
Chicago, IL
My Phone Number
+1 (312) 401-7393
Email
In Rate Out Rate
$250 $250

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

HEY WHATS UP :)My Name Is Diego, I'm a Very Clean 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 WelcOm... (more)
I'm #5 on the map Chicago, IL
My Phone Number
+1 (773) 426-1145
Email
In Rate Out Rate
$200 $250

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
+1 773-413-8086
Email
In Rate Out Rate
$225.00 $250.00

AUTHENTIC ! ( No worries )

 Fun experience with a cool guy ,also with more pics to share upon request, im very athletic and my ad is genuine with accurate pictures and information  ,YOU WILL NOT REGRET inquiring  my company! ! I provide a vast array of options such as personal training or martial arts, dominati... (more)
I'm #7 on the map Chicago, IL
My Phone Number
+1 (312) 477-1760
Email
In Rate Out Rate
Ask me asm me

Toned Pre-med Student

Hi guys! I am an easy-going fit student, new to Chicago, who enjoys meeting nice guys of any age. I have a lean, athletic build and I enjoy working out, martial arts, and reading. I don't meet a lot of guys, which keeps things relaxed and fun, and tend toward more vanilla activities. You can be... (more)
Chicago, IL
My Phone Number
+1 (773) 418-2921
Email
In Rate Out Rate
n/a $240

Actively Looking
18 Versatile Cut

Lets have fun

Hello, thank you for checking out my ad. My name is Ron, I'm 18 years old And just started college. I'm very athletic, I enjoy exercising and staying in shape. Took ballet for 3 year along with karate for 4. I'm Very talented and intelligent. I enjoyianything and like to try new things; very open mi... (more)
Chicago, IL
My Phone Number
+1 (630) 624-8775
Email
In Rate Out Rate
Ask me $250

Actively Looking
37 Top Cut

The Best Top In Chicago 310-927-9484

  I always deliver, never under perform.I can be your passionate boyfriend or a dominant and aggressive pig.  i get into most every scene, .if you have any questions feel free to ask. I absolutely enjoy what i do and i'm good at it.  i'm well reviewed, i dont play games or watch ... (more)
Chicago, IL
My Phone Number
+1 (310) 927-9484
Email
In Rate Out Rate
Ask me $250

Actively Looking
- Versatile Cut

Military Beefy Hairy Charming Educated Sweet Stud

Professional muscle bodybuilder great personality, mild to wild escort or sensual massages.  I enjoy all types of places food music available for travel.   I am lucky to meet great guys from this site.... I have a big sweet smile charming kind heart traveled intelligent up for intimacy rom... (more)
Click to open map Chicago, IL
My Phone Number
+1 (646) 807-9356
Email
In Rate Out Rate
$200 $280

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.
I'm #9 on the map Chicago, IL
My Phone Number
+1 (312) 483-7976
Email
In Rate Out Rate
Ask me Varies

Meeting all your bottom line needs

You can HAVE IT ALL with me! I'll let you release you top concerns tension for bare release. I'll let you enjoy my body also while I enjoy yours regardless of the body type. All sessions come with a guarantee. My discreet and private home in Lincoln Park is open any time for you! Feel free to c... (more)
I'm #10 on the map Chicago, IL
My Phone Number
+1 (619) 318-3801
Email
In Rate Out Rate
$175 $175

Actively Looking
- Versatile Cut

Hairy Muscle Educated Sweet Stud Beefy Military Top Quality Escort ALL MAN ! SOLID BIG FOOTBALL LEGS.BEAUTIFUL PROPORTIONAL BODY HANDSOME

Professional escort horny discrete muscle, great personality mild to very wild escort sensual massages Big Blonde Adonis. Thick in all the right places... Bubble Ass. I enjoy all types of place, food music, available for travel in U.S.... I am lucky to meet great guys from this site. Sweet smile kin... (more)
Click to open map Chicago, IL
My Phone Number
+1 (646) 807-9356
Email
In Rate Out Rate
$200 $280

I'm a graduate student in Chicago looking to make a few new connections.   Treat me with respect and I'll do the same for you. I cannot answer calls from blocked or private numbers.   Like to know more? Don't hesitate to contact me. I'm pretty friendly. I make every effort to respond t... (more)
Chicago, IL
My Phone Number
+1 (312) 972-9793
Email
In Rate Out Rate
Ask me $220

Return to Chicago July 10!

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

(UPDATED) Dtn Boy Next Door: I'm a dork, and its ok to laugh

My profile may seem different from others on here and well, that's because I am. Im not gonna talk about my raging hard cock, or how much I can benchpress. I like getting dressed up to look sharp when meeting a client, it makes me feel confident about myself and you're spending your hard earned... (more)
I'm #13 on the map Chicago, IL
My Phone Number
+1 (719) 924-7040
Email
In Rate Out Rate
$200 $250

Enjoy

Let me know what you have in mindtext/email preferred  
I'm #14 on the map travel adChicago, IL
My Phone Number
+1 (312) 854-9204
Email
In Rate Out Rate
Same + room @ steamworks $180/hr, 300/2hrs

Young Blond Student

Hey- My name's Blake and I've been living in Chicago for three years now. Currently attending school in the city. I've got a great smile and a winning personality. I'm educated, energetic, and here to please. We can meet in my residence in North Uptown or at your apartment/hotel or anywhere in Chica... (more)
I'm #15 on the map Chicago, IL
My Phone Number
+1 8472760010
Email
In Rate Out Rate
$200/hr $200/hr

Have it YOUR way

This is your time. You deserve to have it the way you want it. That's where I come in. No questions, no quarrels, nothing except whatever YOU desire. I have a sexual appetite that keeps me working overtime... and i don't mind putting my work in. Six foot, 160 lbs, slim to athletic build, brown hair ... (more)
I'm #16 on the map Chicago, IL
My Phone Number
+1 (630) 607-2867
Email
In Rate Out Rate
$200 $200

12in HOSTING 150INCALL LAKEVIEW CALL ME NOW

Iam the complete package of everything your looking for more 12in clean cut thick ddf you will not be disappointed im a tall handsome young companion a real play boy so any time with me i would love to show you how to have fun and you will love having me your pleasure is my only focus as well a... (more)
I'm #17 on the map Chicago, IL
My Phone Number
+1 (773) 628-3772
Email
In Rate Out Rate
$150HR 250/2hrs 300/3hrs $200+

page of 6
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!