Mature Escorts in Chicago (29)

Featured Gold Mature Escort
Isabella of Chicago
Isabella of Chicago

Escort Chicago, Loop,Mag-Mile & All Suburbs

Extraordinarily Beautiful Mature,40HH ,Buxom Cougar. Come see what lies beyond the Ordinary! XO

All Escorts (212) VIP (39) What's New (80) Available Now (75) Exotic (46) Middle Eastern (5) Native American (4) Pacific Islander (3) Eros Verified (150) Video (9) GFE (2) Visiting (54) Independent (174) Agencies (4) Mature (29) Centerfolds (4) European (37) BBW (10) Super Busty (96) XXX Stars (8) Alternative (7) Super Booty (21) College Girls (9) Petite (14) All Natural (31) Blonde (80) Brunette (140) Redhead (14) Asian (20) Ebony (28) Latina (53) Caucasian (120) Incall (167) Outcall (164) For Couples (118) For Women (70) For Groups (40) For Trans (25) For Men (206)
Tap for available now

Display

Isabella of Chicago
Isabella of Chicago

Loop,Mag-Mile & All Suburbs

Escort Chicago, Loop,Mag-Mile & All Suburbs

Extraordinarily Beautiful Mature,40HH ,Buxom Cougar. Come see what lies beyond the Ordinary! XO

Berkley Madison
Berkley Madison

Chicago & Surrounding Areas

Escort Chicago & Surrounding Areas

Visiting until October 17th, 2018

Dallas Finest Beautiful Berkley Back!

Nicole
Nicole

Chicago, Loop, Ohare & Surr Burbs

Escort Chicago, Loop, Ohare & Surr Burbs

Sweet & Sexy Lady

Asian Lily
Asian Lily

Downtown, O'Hare, Oakbrook, Suburbs

Escort Chicago, Downtown, O'Hare, Oakbrook, Suburbs

Chicago Hotels OutCall Massage By Asian Lily ( Hotels or Homes )

Elaina Amhurst
Elaina Amhurst

Escort Chicago

Chicago's perfectly petite paramour. The mature dating experience that you have been waiting for.

Brooke
Brooke

Schaumburg, Hoffman Estates

Escort Chicago, Schaumburg, Hoffman Estates

Visiting until October 8th, 2018

Classic Elegance

Amy 34 Double EE
Amy 34 Double EE

Schaumburg, Chicago

Escort Schaumburg, Chicago

Come visit me at my private playroom.

Camile Class
Camile Class

Ohare, Downtown, All Suburbs

Escort Chicago, Ohare, Downtown, All Suburbs

Not Getting Enough Attention at Home?

Kristy
Kristy

Addison Dupage County

Escort Chicago, Addison Dupage County

I'm 5'6, 130 lbs. and a natural 36C-26-36.

e.b. cotenord, NorthShore companion
e.b. cotenord, NorthShore companion

Chicago, Suburbs, Heaven

Escort Chicago, Suburbs, Heaven

Lead me into temptation and deliver me straight to sin

Lesley Baby
Lesley Baby

Chicago, North, West, South suburbs

Escort Chicago, North, West, South suburbs

NEW!!! Super Sweet and Sexy Blonde!!!

C.C
C.C

Western suburbs

Escort Chicago, Western suburbs

Ooo-la-la

Ellie
Ellie

Chicago and Burbs

Escort Chicago and Burbs

I am a classy, charming and like to have a good time.

Jamielynn
Jamielynn

Chicagoland

Escort Chicagoland

Petite Mature Blonde

Massage by Brooklyn
Massage by Brooklyn

Michigan Ave/Illinois St - Downtown

Escort Chicago, Michigan Ave/Illinois St - Downtown

Michigan Avenue/Illinois Street! Hot, Sexy Sensual Body Rubs +Plus.

Fun-Lovin' Jackie
Fun-Lovin' Jackie

Naperville, Rockford

Escort Chicago, Naperville, Rockford

Come have fun with me!

Melanie
Melanie

Chicago-West Burbs/North West Burbs

Escort Chicago-West Burbs/North West Burbs

“DANGEROUS CURVES...IN ALL THE RIGHT PLACES”

Catherine
Catherine

Oakbrook, Lombard, Downtown

Escort Chicago, Oakbrook, Lombard, Downtown

Visiting until NOVEMBER 10th!!!

Elite and Sweet for true Gentlemen back in Chicago!!!!

Anita Love
Anita Love

NW Suburbs, outcalls to suburbs

Escort Chicago, NW Suburbs, outcalls to suburbs

Come on a sensual passionate date with Anita Love!

Jackie
Jackie

North West Suburbs

Escort Chicago, North West Suburbs

Visiting OCTOBER 3-JANUARY 1,2019

At 40 years of age, I am 5'4, 115 lbs., 36D-24-34, with long blonde hair and green eyes.

KITTEN 40H
KITTEN 40H

Illinois, Indiana & Michi

Escort Chicago, Illinois, Indiana & Michi

Super Busty Luscious Italian Beauty with Curves In All The Right places!

Brittany Marie
Brittany Marie

Chicago, Northwest Indiana, S Bend

Escort Chicago, Northwest Indiana, S Bend

I love to spend quality time one on one with a discerning gentleman. I always plan to have great fun

Daphne Dixon
Daphne Dixon

Chicago & vicinity

Escort Chicago & vicinity

Goddess of the Great Lakes

Haley St. James
Haley St. James

O'Hare Oakbrook Lisle Loop NW burbs

Escort Chicago, O'Hare Oakbrook Lisle Loop NW burbs

Welcome to Haleys World..Anything But Ordinary..Shy and Playful all natural 34DDD Blonde Beauty..

Renne' Of Chicago
Renne' Of Chicago

Oak Brook Area / Downtown Area

Escort Chicago, Oak Brook Area / Downtown Area

NEW PICS !!!! 40 Yr OLD WITH BODY OF 20 Yr OLD....

Top Rated VIP-Companion in Chicago
Top Rated VIP-Companion in Chicago

Chicago Downtown, O'Hare, Suburbs

Escort Chicago Downtown, O'Hare, Suburbs

Sensuous, Mature, VIP-Companion now available in Chicago Downtown+O'Hare

Jennifer-Bbw
Jennifer-Bbw

Chicago, O'Hare

Escort Chicago, O'Hare

Treat yourself! Chicago's favorite mature busty bbw

CAPTIVATING CORY-Nations Top Ranked
CAPTIVATING CORY-Nations Top Ranked

Edgewater, North Side, Chicago

Escort Edgewater, North Side, Chicago

VISITING OCT. 25-30th ~ HIGHLY ACCLAIMED UPSCALE MATURE COMPANION ~ The Art Of Intimacy Resonates Deeply Within My Essence ~ Passionate Healer & Confidante ~ Bondassage & Elysium Practitioner ~ Fetish Friendly ~.OUR CONNECTION AND OUR MEMORIES WILL NOT BE SOON FORGOTTEN!

HIGHLY ACCLAIMED TOP RATED~MATURE~REDHEAD VIXEN~PASSIONATE HEALER & CONFIDANTE! BONDASSAGE & ELYSIUM

ZaSu Knight
ZaSu Knight

Chicago O'Hare

Escort Chicago O'Hare

Visiting Chicago O'Hare on October 24th - 26th!

America's Porn Star is ready and waiting for you!

Back to Top