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

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Specialties




















Body Hair






Build








Safe Sex




93 male escorts and male masseurs In Chicago, Illinois

card grid realtime
Previous
page of 5
Next

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.

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

Military Beefy Hairy Charming Educated Sweet Stud

Professional muscle great personality, mild to wild escort or sensual massages. I enjoy all types of places, food, music, available for travel.  Recent client comments, "Beautiful body very proportinal. Handsome, very easy to get along with, nice guy, true boyfriend experience, or mild to wild,... (more)
I'm #2 on the map Chicago, IL
My Phone Number
Mobile+1 (646) 807-9356Home+1 (646) 807-9356
Email
In Rate Out Rate
$220 $280

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

This is an Experiment

I've heard repeatedly that escorts are often hired just to provide companionship. So, I'm testing this theory out. I'm energetic, funny, fun-loving, and always looking for an adventure. I appreciate both high culture and low culture. I'm a perfect companion for a night at the opera or a matiné... (more)
Chicago, IL
My Phone Number
Mobile+1 (773) 888-1574
Email
In Rate Out Rate
Ask me $125.00

CHICAGO'S HAIRIEST GINGER OTTER!

I will be at the buckwood campground this weekend in Indiana. If you are looking for the hairiest ginger in Chicago, then I am your man! I am a young, educated college student. Fiery red head available for your desires. I clean up well for dinner and special events, also a great ... (more)
Chicago, IL
My Phone Number
Mobile+1 (773) 574-0912
Email
In Rate Out Rate
$220 $200

Hookies Mr. Chicago 2014

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

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

September 1 - September 4: CHICAGO

8/28: LAST DAY IN SAN JOSE!8/29 - 9/1: San Francisco 9/1 - 9/4: Chicago9/4 - 9/6: San Francisco 9/6 - 9-16: West Hollywood/Los AngelesI can host in my great Boys Town suite or travel anywhere nearby. I'm a Vers/Top, but it doesn't need to go there. I like a guy who appreciates my endowment... (more)
I'm #4 on the map travel adChicago, IL
My Phone Number
Mobile+1 415-609-2487
Email
In Rate Out Rate
ASK ME ASK ME

Actively Looking
24 Top Cut

...

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

Award-Winning Porn Star in Chicao 8/31 to 9/3 only.

Looking for two overnights!Explorative and educated, I do like to try new things. I am currently in college for medicine, so I can continue a conversation if that is what you desire. If not, we can get to business. I don't offer the boyfriend experience in public. Only while we are indoors. I l... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (615) 681-7193
Email
In Rate Out Rate
Ask me $300

CLEAN, Dominant , STUD

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 #5 on the map Chicago, IL
My Phone Number
Mobile+1 3128591581
Email
In Rate Out Rate
Ask me asm me

Midwestern Bubble Butt *PORNSTAR*

Lets have some fun! Private Gallery Password is:  enter  Also there is plenty of pornography to see what you’re getting :-)100% Discretion assured!Companionship and conversation are a no brainer for me - whether its cocktails and dinner you'd like, you just need some man to man time ... (more)
Chicago, IL
My Phone Number
Mobile+1 (402) 871-6928
Email
In Rate Out Rate
$220 $260

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

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

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

100% Pure Texas Beef

Fun, discreet, genuine and respectful Southern gentleman here. If your looking for a tall, hairy, masculine guy that is easy going and adapts well to any situation, well congratulations...u found him. At 6' 4", 220#, I am 100% Grade-A Texas beef. Can go from mild to wild and can be dominant or submi... (more)
I'm #8 on the map travel adChicago, IL
My Phone Number
Mobile+1 (323) 450-7343
Email
In Rate Out Rate
$200 $200

Ambitious, friendly, sexy boy.

Hey guys, my name's Evan. I'm a Chicago native and very excited to visit my home city for a week. I'm a fun, smart, young guy now living in DC. 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 ... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (202) 643-4560
Email
In Rate Out Rate
$250 $300

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

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

Brown, Hard and ready! 11 inch Hershey Bar!

What's up everybody!?!? What you have here is not your typical entainer for the evening. I'm the REAL DEAL! I'm masculine, muscular "Very Hung", dominant and articulate. I'm open to practicing new fettish and role play. I can travel or host. When it comes to making appointments just email, text or c... (more)
I'm #9 on the map Chicago, IL
My Phone Number
Mobile+1 7087379133
Email
In Rate Out Rate
ask ask

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

GENUINE & PASSIONATE: VISITING SEPT 4-8 ONLY

Hi! My name's A.J. I'm, 5'6", 145-150lbs., athletic/muscular build. Ripped, tight and smooth body, hairy legs (below knee), 6.5" thick cut cock, low hanging balls and In great shape...I have black hair, brown eyes, tan & soft smooth skin, clean cut, masculine, and from what some have said a pret... (more)
Chicago, IL
My Phone Number
Mobile+1 (714) 743-5652
Email
In Rate Out Rate
$250 $300

Previous
page of 5
Next
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!