Business Portraits & Headshots

Our studio is located at
5339 W Lake St., Suite 427
Chicago IL 60644

Our business headshot and portrait packages are designed to provide exactly what you need without unnecessary extras. Choose anything from a single polished image for LinkedIn to a full suite of professional shots for Instagram. Each session includes one retouched image, with additional images available for purchase.

After your shoot, we’ll send watermarked proofs for you to select from. Final retouched images are delivered within 2-5 days.

Book Your Shoot Now

30-Min Session

Designed mostly for businss people who need a new headshot
$ 249
  • Closeup, 3/4 & full body
  • Color or B&W
  • 1-2 Background Changes
  • 1-2 Clothing Changes
  • 1 Retouched Image


Designed mostly for businss people who need a new headshot
$ 499
  • Closeup, 3/4 & full body
  • Color or B&W
  • 2-4 Background Changes
  • 2-4 Clothing Changes
  • 1 Retouched Image


Designed mostly for businss people who need a few shots
$ 749
  • Closeup, 3/4 & full body
  • Color or B&W
  • 3-5 Background Changes
  • 3-5 Clothing Changes
  • 3 Retouched Images


This ultimate experience is designed for business people who need a variety of branding images
$ 1799
  • Closeup, 3/4 & full body
  • Color or B&W
  • 4-7 Background Changes
  • 4-7 Clothing Changes
  • 15 Retouched Images
  • All Images in High Resolution

Group Rates


In Our Studio
$ 745
  • Closeup, 3/4 & full body
  • Color or B&W
  • 1-2 Background Changes
  • 1-2 Clothing Changes
  • Optional retouching packages


On Location Rates begin at
$ 995+
  • 5 or more people
  • Closeup, 3/4 & full body
  • Color or B&W
  • 1-2 Background Changes
  • 1-2 Clothing Changes
  • Optional retouching packages
  • Realtime & online proofing
  • Automated delivery

Upgrade Options

You can add these services at any time.

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: $99 each

Professionally retouched by hand to make you look your best!

5 Retouched Images: $399

Professionally retouched by hand to make you look your best!

10 Retouched Images: $699

Professionally retouched by hand to make you look your best!

50 Retouched Images $2799

Professionally retouched by hand to make you look your best!

100 Retouched Images $4999

Professionally retouched by hand to make you look your best! *pricing may vary for large groups

Comp Cards

  • 100 Model Composite Cards: $299
  • 250 Model Composite Cards: $399
  • 500 Model Composite Cards: $499

Hair & Makeup

  • On-site Make-up Artist One Look: $225
  • On-site Hair Stylist One Look: $225
  • Hair and Make-up Together One Look: $275
  • Hair and or Make-up Together Two Hours: $350
  • Hair and or Make-up Together Three Hours: $475
  • Hair and or Make-up Together Five Hours: $700
Pricing covers one person only and this service must be booked in advance to ensure a service provider is available on site. If you only require hair and makeup for one look, our stylist and/or makeup artist will perform their services at the start of your session and will depart once the photography begins. If you are planning multiple looks and require continuous on-set presence, it is advisable to book the hair and makeup services for the full duration of your session. The initial hair and makeup preparation time is not included in your photography session duration. Please contact us for a customized quote if your shoot involves multiple individuals. In the unlikely event that a service provider is unavailable, we will promptly reschedule your session.


The information is this section pertains to shoots with individuals in our studio. The workflow for team shoots will be similar but slightly different as team shoots may not involve retouching and subjects may be asked to select their images immediately following their session.

Booking and Payment Process

Clients can begin by visiting our website, where they can access our rates and use our online booking system. Once the session type is selected, and a date and time for the photoshoot are selected, a non-refundable deposit is required to secure the booking. This deposit will be applied towards the total due for the session. The balance is due at the end of the photoshoot; however, clients will receive an email a few days before the session, offering the option to pay in full. Alternatively, clients can opt to pay for the entire session at the time of booking.

After booking, clients will receive a survey to detail their specific needs and session objectives. This ensures all requirements are clearly understood. If necessary, clients can also book a Zoom session at that time to discuss specifics.

Clients wishing to schedule a Zoom consultation before booking their shoot can initiate the process by filling out our contact form.

Photoshoot Process

Step 1: Arrival and Preparation On the day of the photoshoot, clients arrive at the studio or a designated location. If makeup and hair services have been arranged, they are completed prior to shooting and do not count towards the session time.

Step 2: The Photoshoot The photographer guides the client through the photoshoot, providing direction on poses and expressions to best capture the desired looks. Different backgrounds and outfit changes are incorporated as planned, ensuring a variety of image styles are available for selection.

Step 3: Review Within a few days of the photoshoot, clients may review watermarked proofs of the images that meet our standards in an online gallery to select their preferred images for retouching. This ensures clients are involved in the selection process and satisfied with the initial results.

Retouching Process

Step 1: Image Selection Clients choose their preferred images from the session. The number of images selected depends on the purchased package, with additional images available for retouching at an extra cost.

Step 2: Professional Retouching The chosen images undergo professional retouching, including adjustments to color, brightness, blemishes, and other enhancements to ensure the client looks their best. This process is carefully performed to maintain a natural appearance.

Step 3: Final Delivery Retouched images without watermarks are delivered to the client in high-resolution via an online gallery. Clients typically receive these images within 2-5 days after making their selections. If a faster turnaround is needed, we can usually accommodate such requests.

Your Path to Professional Photos

This streamlined process is designed to be transparent and efficient, ensuring a smooth experience from booking to the final delivery of stunning, professionally retouched images. Each step is handled with the utmost professionalism to meet and exceed client expectations, making John Gress Photography an excellent choice for those seeking quality and reliability throughout the photographic process.

About Us

Chicago corporate headshot photographer John Gress collaborates with numerous corporations to enhance their executive and staff branding with top-quality professional headshots. Suitable for business websites, LinkedIn, and other social media platforms, Gress provides flexible photoshoot options either on-location or at his studio located at 5339 W Lake St., Suite 427, Chicago, IL 60644. His service ensures a seamless match with your existing commercial photography, maintaining a consistent style across all new employee headshots on your corporate website. Explore the breadth and quality of our work by visiting our portfolio, where each image reflects our expertise and commitment to excellence in professional photography.



Deposit: Clients have the option to either pay in full or make a non-refundable deposit of $150 with a credit or debit card at the time of booking to secure their session date and time. This deposit guarantees your slot and prevents other bookings for that period. Please note that this deposit is non-refundable, regardless of any changes or cancellations to the appointment.

The deposit will be deducted from your final bill, with the balance due immediately after your session. Payment can be made via cash, credit cards, Zelle, Venmo, or PayPal.

If you request hair and makeup services and we cannot schedule a service provider for your photoshoot, we will refund your deposit if rescheduling is not possible. For sessions requiring extensive services such as hair, makeup, and styling, a higher deposit may be required. By booking an appointment, you grant John Gress Media Inc. permission to use the retouched images from the session for commercial purposes.

Rescheduling: You may reschedule your shoot for any reason, provided you notify us at least 48 hours before the scheduled time, without forfeiting your deposit.

Retouching: We specialize in natural retouching aimed at enhancing your appearance while preserving your authentic look—well-rested, healthy, put-together, and blemish-free. We strive to present the best version of you, subtly making you appear a little younger without altering your essential features. Each image includes up to three rounds of retouching, although most images typically require only one. Additional retouching is available for $10-30 per round, depending on the complexity of the adjustments required.

While we endeavor to meet all client requests, our focus is on natural studio and location shoots. We do not specialize in heavy alterations or composite images. For specialized retouching needs beyond our scope, you are welcome to take the images to external service providers.


Terms for Group Sessions on Location

Clients will be asked to sign a contract that requires a 50% deposit to secure the booking. The remaining balance is due within 30 days after the shoot. Payments for both the deposit and the final balance can be made via credit card, electronic funds transfer (EFT), or company check.


Chicago Headshot Photographer FAQ’s

Answered by John Gress, Chicago Business Headshot Photographer

What exactly are headshots?
Headshots are professional photos typically focusing on the head and shoulders, designed to reflect a polished and professional appearance. They can be styled in various ways to meet the specific needs of professionals across industries.

How many images do I need?
The number of images you need may vary depending on your professional requirements. For most business professionals, a few high-quality images are sufficient to enhance their LinkedIn profiles, company websites, and other professional platforms.

What is a ‘look’?
In professional headshot photography, a “look” can be defined as a variant of your portrait with a particular outfit and style. Each look captures different aspects of your professional persona, allowing for a versatile portrayal of your professional image.

What do you mean by retouched images?
Retouched images are professionally enhanced to correct color, lighting, and minor blemishes, ensuring the photos present the best version of yourself. The goal is to keep the enhancements subtle and maintain your natural appearance, optimizing for a professional context.

What should I wear?
For professional headshots, it’s essential to wear business attire that aligns with your industry’s standards. Opt for neat, well-fitting outfits in solid colors to ensure a professional appearance. Avoid busy patterns that can be distracting and detract from the primary focus—your professional presence.

What should my expressions be like in the images?
Your expressions should convey professionalism and confidence. It’s important to have a relaxed and approachable demeanor. I will guide you through various poses and expressions during the shoot to capture your professionalism effectively.

Do I need a makeup artist or hairstylist?
While not always necessary, a professional makeup artist can enhance your features and ensure you look your best under studio lighting. For men and those with short hairstyles, a hair stylist may not be essential. However, having a professional handle your makeup and hair can significantly elevate the quality of your headshots, especially for more diverse looks.

Can I choose different backdrops for my headshot?
Absolutely! We offer a variety of backdrops to suit your specific needs and align with your company’s branding. Whether you prefer a traditional solid color, a modern textured look, or a custom backdrop that reflects your corporate identity, we can accommodate your vision. This flexibility ensures that your headshots not only look professional but also complement and enhance your business’s branding efforts.

Book Your Session Today

Don’t miss the opportunity to elevate your team’s professional image. Booking a group session with John Gress ensures that your company’s first impression resonates with excellence and professionalism. Our tailored approach guarantees that each photo aligns perfectly with your brand, supporting your business goals and enhancing your corporate identity. By securing your booking today, you take a pivotal step towards showcasing the professionalism and unique character of your team. Invest in your company’s future by choosing John Gress for corporate photography that stands out in today’s competitive market.