Headshots Chicago

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1 Retouched Headshot

30 MInutes

1 Outfit/ Look



3 Retouched Headshots

75 Minutes

2 Outfits/ Looks

Downloadable Digital Gallery



5 Retouched Images

120 Minutes

3 Outfits/ Looks

Downloadable Digital Gallery

On-Site Staff & Group Headshot Sessions Available. Please Reach Out to Discuss Custom Pricing.

Contact me to discuss the specific needs of you or your team. I will work with you to develop a customized package within your budget to solve all your specific requirements and desires.

Chicago Headshots Photography

  • ✔ Professional since 2008
  • ✔ Contemporary Photography Style
  • ✔ Free Reshoot or Money-Back Guarantee
  • ✔ Retouching Included – No Hidden Fees
  • ✔ Fun and Painless

You’ve heard “never judge a book by its cover” so many times that it’s probably lost meaning—and yet, the words still hold true. People look at headshots and judge individuals 1/10th of a second. That’s right. Your success can hinge on whether you come across as pleasant, positive, trustworthy, and competent. You literally can’t afford to leave such an important detail to someone who isn’t experienced. Whatever industry you’re in, whether corporate, business, or acting people are going to take one look at that picture and in that split second will make a decision about whether or not they’re interested.

When it’s time to take a professional headshot, don’t leave it up to chance or an inexperienced friend. Contact Chicago photographer Kyle Bondeson. With more than a decade of full-time professional studio photography experience, he guarantees the highest quality work, at prices that won’t empty your bank account—really! Take a look at his pricing page and see for yourself. There are no hidden retouching fees, outfit upcharges, proof sheet deposits, etc. If you don’t see something in your price range, contact him, and he’ll work with you.

Maybe you’ve had a lousy previous experience with photo shoots. Uncomfortable, awkward, expensive—it doesn’t have to be that way. Kyle’s goal is to provide high-quality professional headshots photography at an affordable price. Quite simply, he loves what he does, and he excels at it.  In fact, Kyle is so confident that you’re going to love your new headshots that he offers free reshoots or your money back if you’re not fully-satisfied.

Whether you’re a Chicago corporate professional in need of a business headshot, an up-and-coming performer looking for new actor headshots, or just need a social media or website headshot, Kyle’s got you covered.


Professional Services Offered:



Should I Wear Glasses In My Headshot?

If you normally wear glasses and people aren’t accustomed to seeing you without eyeglasses, you will want to wear them for your headshots!

If you do not often wear glasses, skip the eyewear.

It’s important that the photographer capture images that best represent you and your style.

Glasses can pose special challenges for the photographer. If you determine you need them for your headshots, it’s best to use glasses with an anti-reflective (AR) coating.

What Should You Not Wear For A Headshot?

If you don’t want to appear as if you’re glowing, avoid white, near-white and neon or fluorescent colors as these will reflect light into your face.

You can, however, wear white when planning to use it with a darker coat or sweater to avoid a “floating head” on a white backdrop.

It’s typically best to opt for cooler colors over warmer colors as cool colors will complement, not accentuate, the natural red tones in your skin.

Avoid busy patterns and logos of any kind as they detract from you, the star of the photo.

Stay away from ill-fitting clothes or clothing you don’t normally wear. By choosing comfortable clothing that you already own and wear, you’ll look more authentic and confident in your headshots.

Lastly, avoid pastels or other flesh tones that are unflattering and wash you out.

Can You Wear Black In A Headshot?

Absolutely. Dark colors provide more contrast in a photo and wearing black for your headshot is a great way to naturally shift focus to your face.

While black is recommended, make sure to also bring a few different color tops that will contrast against different backgrounds.

Should You Wear Jewelry In A Headshot?

Less is more when it comes to headshots. Unless you represent a jewelry brand or certain jewelry is part of your signature look, it’s generally not recommended to wear these accessories in your headshots.

If you feel jewelry is essential to your headshots, I recommend keeping it to a minimum and avoid oversized pieces or dangling earrings that can be distracting and interfere with flattering poses.