Book Now with Heather Riley.
Use this form to submit a booking request for The Best Escort in Chciago.

Booking Heather Riley: The Ultimate Companion Experience

Chicago’s premier GFE companion. For men who know the difference.

Whether you’re looking for a moment of intimacy, a night of conversation and chemistry, or an unforgettable public date—you’re in the right place.

I offer a range of curated experiences for those who value connection, discretion, and a little indulgence. There’s no pressure here, just pleasure—with presence.

Private GFE Companionship

$1,000/hour – No minimum

My GFE is a full-bodied experience. Think warmth, affection, attention, laughter, and that electric feeling of being truly seen. Whether we’re spending one hour together or five, I bring the kind of energy that lingers.

This is perfect for:
• Private one-on-one time
• Hotel visits, stay-ins, or relaxed multi-hour connections
• Clients who want emotional presence alongside sensual chemistry

Shorter sessions are available at my discretion.
Discreet gentlemen who know how to carry themselves are always welcome.

Screening is required. No exceptions.

Social Date — $500 Flat Rate

Public companionship only. No intimacy included.

Want to take me out and show me off? Whether you’re nervous, curious, or just dying to be seen with me, this flat-rate public date gives you a taste of what it’s like to share a night with someone unforgettable.

What it includes:
• 3–6 hours of public time (dinner, events, games, cocktails)
• One-on-one attention, authentic conversation, magnetic presence
• No intimacy. Just connection.

Perfect for:
• White Sox games, United Center suites
• West Loop dinners and rooftop drinks
• Playpen afternoons on Lake Michigan
• Fine dining at Sepia, Bavette’s, or Gilt Bar
• Weddings, galas, VIP parties, or anything that requires a little elegance on your arm

Want to extend our date into something more private?
Just let me know in advance. My full GFE rates will apply.

Fly Me to You (FMTY)

Not in Chicago? Bring me to you.
I travel for respectful, well-screened clients.
First-class airfare, hotel accommodations, and a 50% deposit are required.

Perfect for:
• Private retreats
• Business travel companionship
• Weekends of indulgence, connection, and no distractions

Let’s make it worth the miles.

Overnights & Extended Dates

Want to spend the night—or the entire weekend—with me?
Multi-hour and overnight rates are available by request.

Extended experiences are prioritized for pre-screened or returning clients. Let’s make magic without the clock watching.

Tour Requests

If you’d like me to visit your city, you’re welcome to request it.
When I receive enough interest from a location, I may offer a short tour.
Pre-bookings and deposits will always be given priority.

Screening & Expectations

Screening is required to secure all bookings.
I accept provider references or professional verification (LinkedIn, company website + ID/email).
Your discretion is as important to me as mine.

I respond best to polite, respectful, and complete inquiries.
Explicit messages, acronyms, or poor behavior will be ignored or blocked.

Booking Me

To inquire about availability, please include:
• Your name
• Desired date, time, and location
• Booking type (GFE, Social Date, etc.)
• Screening info