Chicago headshot photography for individuals, executives, and corporate teams. Our headshot sessions are designed for everything from a quick LinkedIn refresh to a full personal branding session. Photographer John Gress creates polished, professional portraits with guided posing and a streamlined process so you leave with images you’re confident using on LinkedIn, your website, email signatures, press releases, and marketing materials.
Studio headshot sessions include a private online gallery of proofs so you can select your favorites. For corporate and team headshots on location, images are reviewed on-site so each person can choose their photo during the session. Final retouched headshots are delivered within 24–72 hours, with expedited turnaround options available.
Add these services before or after your session.
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.
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.
Professionally retouched by hand to make you look your best!
Professionally retouched by hand to make you look your best!
Professionally retouched by hand to make you look your best!
Professionally retouched by hand to make you look your best!
Professionally retouched by hand to make you look your best!
Individual Sessions
Teams & Large Groups
For on-location team sessions or large groups, booking half-day or full-day HMU ensures consistent grooming and touch-ups for all participants throughout the shoot.
Step 1: Arrival and Preparation — On the day of your photoshoot, arrive at our studio (or your scheduled location). If hair and makeup services are arranged, they will be completed before the session and do not count toward your booked time.
Step 2: The Photoshoot — John will guide you through a variety of poses and expressions to capture polished, professional images. Multiple outfits and backgrounds are included as outlined in your package.
Step 3: Review
Step 1: Image Selection — From your gallery, you’ll choose the images included in your package. Additional selections may be purchased for retouching at any time.
Step 2: Professional Retouching — Our standard retouching enhances your natural look by refining color, light, blemishes, stray hairs, shine, and minor distractions while maintaining a natural and professional appearance. This may include reducing facial wrinkles and softening under-eye bags to create a rested, polished look.
Composite work, body reshaping, heavy alterations, or extensive background changes are not included in standard services. In many cases, these can be provided for a custom fee depending on complexity. If a request falls outside our scope, you are welcome to use outside retouchers once our work is complete and delivered.
Step 3: Final Delivery — Retouched images are delivered in high resolution via an online gallery, watermark-free. Turnaround is typically 24–72 hours after selection, though same-day delivery is often possible at no additional charge.
Our process is simple, transparent, and efficient — from booking through delivery. Every step is handled with care and professionalism so you walk away with images you’re proud to share. Whether you need LinkedIn headshots, executive portraits, or a full branding package, John Gress Photography delivers a seamless experience and outstanding results.
Chicago corporate headshot photographer John Gress works with companies of all sizes to create consistent, high-quality portraits for executives and staff. These images elevate your professional presence across websites, LinkedIn, email signatures, press releases, and other corporate communications. Sessions can take place in our Chicago studio at 5339 W Lake St., Suite 427, Chicago, IL 60644, or on location at your offices. With professional lighting, real-time proofing, and a collaborative approach, each subject leaves confident in their image.
Explore the breadth of our work by visiting our portfolio, where each image reflects our expertise and commitment to excellence.
Retainer (First Payment): A 30% non-refundable retainer is required at booking to secure your session date and time. This amount is applied toward your total. The remaining balance is due on the day of your session. Payment may be made via credit card, ACH (eCheck), Apple Pay, Google Pay, cash, Zelle, Venmo, or PayPal.
Rescheduling: You may reschedule with at least 48 hours’ notice and your retainer will be applied to the new date. Rescheduling requests with less than 48 hours’ notice may require a new retainer.
Cancellations: All retainers are non-refundable. If you cancel rather than reschedule, your retainer will be forfeited.
Hair & Makeup: If you request hair and/or makeup and we cannot schedule a provider, we will refund your retainer if rescheduling is not possible. For sessions requiring multiple service providers or extended coverage, a higher retainer may be required.
Image Rights: Clients are granted personal usage rights for their images. This includes use for professional promotion (LinkedIn, websites, resumes, corporate communications, speaking engagements) and local marketing (such as real estate, insurance, or law firm advertising). Commercial use — such as national advertising campaigns, product packaging, or book covers — requires a separate license. By booking, you grant John Gress Media Inc. the right to use retouched images for portfolio, website, social media, and promotional purposes.
Retouching: Our standard retouching enhances your natural look by adjusting color, light, blemishes, flyaways, background cleanup, and minor clothing wrinkles while maintaining authenticity. Background changes for close-up headshots may be available, but full-body background replacements are not included. Composite work, heavy alterations, extensive background changes, or body reshaping are considered advanced editing and may be available for an additional custom fee. Each image includes up to three rounds of adjustments; additional edits are available for $30 per round. Clients seeking extensive edits beyond the scope of our work may use outside retouchers once files are delivered.
For corporate team sessions booked on location, a signed contract and 50% retainer are required to secure the date. The remaining balance is due within 30 days. Payment may be made via credit card, EFT, or company check.
What exactly are headshots?
Headshots are professional portraits that focus on your face and shoulders, designed to reflect a polished and approachable appearance.
How many images do I need?
Most professionals need just a handful of strong images for LinkedIn, corporate websites, and other platforms.
What is a ‘look’?
A “look” refers to a distinct outfit, styling, or backdrop. Small changes, such as adding or removing a blazer or tie, are considered part of the same look, not a separate one.
What do you mean by retouched images?
Retouched images are carefully refined to correct lighting, color, blemishes, shine, flyaways, and other distractions while maintaining a natural, professional appearance.
What should I wear?
Choose business attire that reflects your industry’s standards. Solid, neutral, or classic colors work best. Bring options (with/without a jacket, different ties or accessories, multiple blouses or tops) to create variety. Avoid logos, bold patterns, or overly trendy pieces.
What about expressions?
Your expressions should convey professionalism, confidence, and approachability. We’ll guide you through poses and expressions to ensure your best look.
Do I need a makeup artist or hairstylist?
While not always required, professional makeup enhances your appearance under studio lighting and provides a base for retouching. Men and those with short hair may not need styling, but a stylist is recommended for women or anyone seeking multiple looks.
Can I choose different backdrops?
Yes. We offer a range of backdrops from clean, solid tones to textured and environmental looks. For teams, we can also match your existing corporate photography style to ensure consistency across your branding.
For over 25 years, Chicago photographer John Gress has created stunning photography and video content for some of America’s largest companies and major international publications. His diverse portfolio spans lifestyle, advertising, portraiture, and video content tailored for the beauty industry, professional sports leagues, and high-profile campaigns. Recognized by Professional Photographer Magazine as “one of the nation’s foremost experts on lighting,” Gress is known for his bold, dynamic style—whether shooting on location or at his Chicago studio at 5339 W Lake St., Suite 427, Chicago, Illinois 60644.
As a commercial photographer, Gress has played a key role in crafting impactful imagery for advertising and public relations campaigns for numerous Fortune 500 companies. His notable client list includes Nike, Coors Light, Windex, Glade, the NBA, Hyatt Hotels, Lufthansa, the WAHL Clipper Corporation, and Panini trading cards.
In addition to his commercial work, his photography has appeared in leading global publications including Time, People Magazine, Sports Illustrated, Rolling Stone, US Weekly, and The New York Times.
In 2025, Gress helped lead Team USA to victory in the World Photographic Cup, the premier international photography competition where top photographers from over 40 countries compete in the “Olympics of Photography.” He was also awarded Best in the Nation for having the highest-scoring image from the United States, helping secure the USA’s first-place finish.
That same year, Gress was honored at the United Nations with a Professional Photographer Achievement Award from the International Photographic Council—a distinction that celebrates excellence in photography as part of a decades-long tradition.
Gress discovered photography as a teenager in his native Oregon, taking his mother’s Vivitar point-and-shoot camera to summer camp. By his senior year of high school, he was already covering major events for the Associated Press. He earned a bachelor’s degree in Political Science from Portland State University in 2000.
His background and breadth of experience allow him to deliver visual content that elevates branding and storytelling initiatives. Combining technical mastery with creative vision and a deep understanding of his clients’ needs, Gress has become a sought-after professional in the industry.
A passionate educator and mentor, Gress is committed to advancing the photographic community. Through Instagram, YouTube, and contributions to leading photography publications, he shares his expertise with a broad audience. He regularly speaks at top industry conferences and leads in-person workshops across the U.S., offering hands-on training in both the technical and creative aspects of photography. His dedication to education continues to shape the next generation of photographers and push the art of photography forward.
