Business Headshots

Set yourself apart from the crowd or give your team a uniform style with headshots from Trainman Photography!

Choose Trainman Photography to put your visual brand on track and make a lasting first impression that shows off your best self!

Our world thrives on visual stimulation which makes the quality and integrity of your professional headshot, effectively your first impression for your future clients and employers, of the utmost importance. Whether displayed on your website, LinkedIn profile, business card, or social media, your professional headshot puts a face to your name, brand, and company. Quality headshots show your future clients and employers that you are trustworthy, professional, and right for the job!

Individual Headshots

Team Headshots

The Trainman Philosophy

Engaging and captivating headshots are captured when you are feeling your most comfortable and confident! This is why at Trainman Photography we are committed to make your photoshoot and the entire headshot process from booking to delivering the retouched images feel more like hanging out with a new friend than just another work chore while capturing attention grabbing headshots that will show the world how incredible you are!

Learn More About The Trainman Process

Individual Headshot Packages

The Business Session: $175

The Business Session is our most basic package and perfect if you are looking for that one great photo to show your clients and colleagues how incredible you are! Put on the outfit that makes you feel ready to take the world by storm for this one look, in-studio photoshoot that typically lasts for 30-60 minutes. We will work together to choose the very best photo for retouching throughout the photoshoot so you'll know when you leave that we captured the perfect shot! Your color/exposure corrected high resolution digital proofs and one retouched and formatted headshot will be ready for you to download approximately 7-10 days after the photoshoot.

Additional retouched headshots are available for $30.

The Full Session: $275

If you love having options then the Full Session is the package for you. Choosing the perfect outfit is hard, so let's do it together! Bring all you can carry and we will spend a 60 minute photoshoot curating several looks on a variety of in-studio backgrounds as well as the possibility for a field trip outside for a series of natural light portraits.Throughout the photoshoot we will work together to choose the very best portraits for retouching and make sure you are thrilled by the images we capture! Your color/exposure corrected high resolution digital proofs and two retouched and formatted headshots will be ready for you to download approximately 7-10 days after the photoshoot.

Additional retouched headshots are available for $30.

On Location Portraits: $425

This photoshoot comes to you! Whether you have an office that's as cool as you are, want to elevate your style surrounded by Chicago's towering skyline, or show off around your favorite neighborhood, we start from scratch to design a portrait session that will bring your vision to life and exceeds expectations! Typically lasting 2-3 hours, this photoshoot will make you a model for the day while we capture all of your best angles in as many looks as you can carry. Throughout the photoshoot we will work together to choose the very best portraits for retouching and make sure you are thrilled by the images we capture! Your color/exposure corrected high resolution digital proofs and four retouched and formatted headshots will be ready for you to download approximately 7-10 days after the photoshoot.

Additional retouched headshots are available for $30.

Team Headshots

A unified look for your unique team members.

Whether your company/firm/family has a handful of employees or offices across the globe, Trainman Photography brings the photoshoot to you! Our portable studio can be set up in any space to create a series of headshots for your team that show everyone off in their best light while retaining a unified look that elevates your brand. Team Headshot packages start at $600 for up to ten team members with headshots for additional team members starting at $55 each. Contact for more information on acquiring Team Headshots!