Chicago Escorts

Find the best Chicago escorts and independent female companions in The Windy City. These lovely ladies provide companionship for dinner & lunch dates, concerts, private events, business trips & travel, and just about any other occasion.


Escorts in Chicago

Updated: July 14, 2022

Natasha James

Natasha James, a Chicago escort and porn star in the USA
  • Age: 29
  • 5’4
  • Auburn hair
  • Blue eyes
  • non-smoker

Natasha is a sexy, educated, and experienced GFE companion who you might recognize from her work in porn. She’s great for dinner dates, overnights, or Fly Me To You type appointments. She’s based in Chicago but can travel to most other cities in the USA and is available to men, women, and couples looking for the ultimate in female adult entertainment.


Sage of Chicago

Sage of Chicago, a mature companion and GFE
  • Age: 40s
  • 5’7
  • Red hair
  • Blue eyes
  • non-smoker

Sage is an educated, outgoing, and mature Chicago escort with great conversation skills and a very laid back personality that will put you at ease.

Mature redhead with a desire to make your day. My easy going nature is sure to set you at ease while my outgoing personality will in a smile show my naughty intentions. I strive to make you smile, your knees weak, and your satisfaction sated. Be it that you need tender care or a bit of a wilder experience…. I can be yours for the taking. Check my site for details on screening, as well as additional pictures.

Sage of Chicago



Escorts Visiting Chicago

Sexy and Mature Chicago Escorts For Any Event or Occasion!
Megan Love

traveling by request only

I don’t have any trips planned for Chicago at this time, and usually only travel to Illinois for Exclusive Dates or for gentlemen who are on my Frequent Flyers List.

If you would like to see me for an Exclusive Date, then please fill out my appointment form with your request.



Are You Planning A Longer Date With A Companion?

Date Ideas For Chicago

If you are booking a longer date with a companion, it’s always best to have some ideas in mind when it comes to places to eat, entertainment venues, sights to see, and other fun activities. Your time together will be much more memorable and enjoyable if you plan ahead. There’s an endless and diverse range of things to do in Chicago, including great food and music, museums, historic sites, theaters, sporting events, and much more.


Where Can I Find Other Companions?

The escorts you find here are available in different parts of Chicago. But they are also available in other cities in the greater metro area. These include:

  • Buffalo Grove, IL
  • Claredon Hills
  • Glencoe
  • Hinsdale
  • Hyde Park
  • Long Grove, IL
  • Naperville, IL
  • Northbrook, IL
  • Oakbrook
  • River North
  • South Barrington
  • Western Springs
  • Wicker Park
  • Wilmette
  • Winnetka
  • Wrigleyville