by Chicago Corporate Headshot Photographer John Gress


Chicago corporate headshot photographer John Gress has worked with dozen’s of corporations to help their executives and front-line employees put their best foot forward with a great headshot on their business website, linked-in and social media.

Whether on location with your whole team or in his studio, located near downtown at 1945 S Halsted St. #300, Chicago IL 60608 in the Pilsen neighborhood. Gress can deliver exactly what you need in a variety of styes and backgrounds on your exact needs. Including matching photography you have had in the past so your new employees headshots fit right in with the corporate headshot photography on your website.

Gress has worked with companies large and small to fill their headshot needs. His business headshot clients have included fortune 500 companies including Hyatt Hotels, venture capital firms including The Pritzker Organization, Law firms, tech startups and many more.

Our pricing and packages are designed to give you the flexibility to get exactly what you need, without having to pay for options you don’t want. Whether you are looking for a single finished image for your LinkedIn, or 20 images for your Instagram, you can get exactly what you need. All sessions include at least 1 retouched image with additional images available for purchase.

After the shoot, we will send you watermarked proofs and you can select the images you need and we will turn them around in 2-5 days.

Our studio is located at 1945 S Halsted St. #300, Chicago IL 60608

All of our shoots include:

  • Unlimited number of photos during your shoot.
  • All images may be shot or converted to B&W or color
  • Online watermarked proofs
  • Access to our Chicago, Illinois photo studio

Book Your Shoot Now


Clicking on the appointment type will reveal our calendar. To book a reservation there is a $150 reservation fee which goes towards your total or you can pay in full. You can call 312-545-5438, email or securely checkout below.

If the dates available don’t work for you, please contact us.


Group Corporate Headshot Sessions On Location

  • 1-5 people $250/person

    Each person will get a personalized session and 1 fully retouched, high-resolution headshot.

  • 6+ people Contact Us

    Groups of 5 or more may qualify for a special group rate, please contact us so we can provide you with a custom quote.

Upgrade Options

All of the images in medium-resolution: $149

Get all of the images from the shoot without watermarks, but un-retouched in medium resolution. This is a great option for people who need the images for online use.

All of the images in high-resolution: $249

(Get all of the images from the shoot without watermarks, but un-retouched in high resolution. This is a great option for people who need the images printed.

Additional retouched images: $79

Professionally retouched my hand to make you look your best!

5 retouched images $329

Professionally retouched my hand to make you look your best!

10 Retouched Images $599

Professionally retouched my hand to make you look your best!

Hair & Make Up

After you book your shoot, just let us know that you would like to add HMU and we will make the arrangements. Your initial hair and make-up look will not count against the time of your session.

      • On-site Make-up Artist One Look: $200*
      • On-site Hair Stylist One Look: $200*
      • Hair & Make-up Together One Look: $225*
      • Hair & Make-up Together Three Hours: $350*
      • Hair & Make-up Together Five Hours: $475 *
*Pricing covers one person only and this service must be booked in advance so we can have a service provider on site. Please contact us for a quote for shoots with multiple individuals.



Cash, Credit Cards, Zelle, Venmo and Paypal are accepted.

Reservation Fee:

A $150 non-refundable reservation fee is due at the time of booking. After receipt of this fee, we will reserve the date and time agreed upon and will not make other reservations for that date and time. For this reason this fee is non-refundable, even if the date is change or the appointment is canceled for any reason. The deposit goes towards your final total and can be paid above on this page, over the phone with a credit card or via Zelle (our address is If you request hair and make-up and we can not schedule someone to attend your shoot, we will refund your deposit if we can’t find a time that works for everyone. A higher deposit may be required if you’re shoot requires two or more of the following: hair, make-up and styling. The balance will be due at the studio at the end of the shoot.


You can reschedule your shoot for any reason 48 hours or more before the shoot.


We specialize in natural retouching that makes you look like you. Well rested, healthy, put together, blemish free, and maybe a few years younger but not lighter. We will do up to three rounds of retouching per image, but rarely is more than one round needed. If you request additional changes you will be charged $10-30 each additional round of retouching, dependent upon the complexity. We will do our best to make any changes you request, but there is a chance your requests may exceed what is possible for us. Most location shots are done at real locations and we do not deal in overly complex composite and/or heavily altered images. However, you are more than welcome to take the images we create to a company who specializes in that type of retouching.