How much do couples typically invest?

Weddings: $5,500–$11,000. Most couples land at $7,000–$9,500 for Jeremy-led coverage with two photographers, 48-hour highlights, and hand-edited galleries. Associate-led collections start at $5,500. Proposals: $750–$1,100. Engagements: $750–$1,050.

How fast will we get photos?

Highlights: 24–72 hours depending on collection. Full gallery: 3–5 weeks, hand-edited by me. Never rushed, never outsourced.

We want great photos but we are self conscious and feel a little scared about not looking good. Will this be awkward?

About 70% of my couples say exactly this. I spent 10+ years as a professional actor, director, and acting coach—including work at Steppenwolf Theatre Company and a Jeff Award. I give you something real to do. You'll be so focused on each other, you'll forget I'm there. That's when the magic happens.

What does your theater background actually do for us?

Three things: 1. I know how it feels to be on camera. 2. I read energy and adapt. 3. I find the moments. You're not performing. You're living your day while I use 10+ years of experience to help you look and feel like yourselves.

What if we have a bold creative vision for our wedding photos?

You're my people. I live for couples who want something unexpected — whether that's elaborate themes, cinematic concepts, or 'what if we did something completely different' ideas. My fine art background and theater training mean I can help you execute ambitious creative visions while still making you feel comfortable in front of the camera. Let's design something unmistakably yours together.

What if we're camera-shy but also want creative photos?

That's not a contradiction — that's most of my favorite couples. Maybe you're introverts who are also massive Star Wars fans. Maybe you want romantic AND cinematic. My theater background helps you feel comfortable enough to forget the camera exists, AND my fine art eye ensures the images are gallery-worthy. You can absolutely have both.

What's the difference between Jeremy-led and associate-led?

Jeremy-led: I'm your primary photographer. $7,000–$11,000. Associate-led: One of my personally selected and trained photographers leads your day. Same artistic direction and editing style—because I edit every single gallery myself. $5,500–$7,750.

Our venue has terrible lighting. Is that a problem?

No. I thrive in low light. Professional gear, mastery of ambient light, and years of shooting in dark churches, candlelit receptions, and nighttime ceremonies. I bring subtle professional lighting your guests won't even notice.

Our venue isn't very photogenic. Can you still make it look good?

There are no boring venues—only boring photographers. I started as a fine art street photographer—I find beauty in unexpected places. Your venue becomes a canvas. I find the light, the angles, the textures. Trust the process.

Do you travel for weddings?

Yes—Chicagoland, Midwest, and destination weddings worldwide. Travel fees apply outside the Chicago area. Share your plans and I'll send a tailored quote.

How do proposal sessions work?

I handle everything: location scouting, timing by light, hidden positioning. I'm in place before you arrive—invisible until after the 'yes.' Then we celebrate with portraits. Highlights delivered within 48–72 hours. Last-minute requests welcome—I accommodate proposals with as little as 48 hours notice.

How much do Chicago corporate headshots cost?

On-site corporate headshot sessions for teams start at $3,295 for a half-day (4 hours) and $6,500-$7,500 for a full day (8 hours). This includes professional portable lighting, backgrounds, professional editing, high-resolution digital files, and full business usage rights. Best for teams of 5 or more employees. Custom quotes available for unique projects or smaller teams.

What makes Jeremy Glickstein different from other Chicago headshot photographers?

I spent 10+ years as a professional actor, acting coach, and theater director—including work at Steppenwolf Theatre Company and a Jeff Award (Chicago's Tony equivalent). That background taught me how to help people feel comfortable on camera and achieve natural expressions instead of stiff corporate poses. Most headshot photographers say 'smile'—I give your team direction that brings out authentic, confident expressions. I also hand-edit every image personally, never AI or outsourced.

Do you come to our office for headshots?

Yes—all our team headshot sessions are on-site at your location. We bring professional portable lighting and backgrounds to your office, conference room, or building exterior. No studio commute required for your team. We handle all setup and breakdown with minimal disruption to your workday.

How long does each person's headshot session take?

It varies by style. Clean corporate headshots are efficient at 5-10 minutes per person. Creative or multi-look sessions take 15-20 minutes per person. For a half-day session (4 hours), we typically photograph 15-25 team members depending on the style chosen.

How fast is turnaround for corporate headshots?

Standard delivery is 7 business days for your complete edited gallery. Rush delivery (48-hour turnaround) is available for urgent needs—perfect for new hires, press releases, or website launches. Rush fees apply.

What types of headshot styles do you offer?

We offer three main styles: Corporate Clean (neutral backgrounds, classic LinkedIn-ready headshots), Environmental (shot in your office with natural context), and Creative Branding (editorial, personality-driven portraits for agencies, startups, and creative firms). We adapt to your brand's needs and can mix styles within the same session.

What are the photo usage rights for corporate headshots?

All images include full business usage rights for websites, LinkedIn, social media, email signatures, print materials, press releases, and marketing. You own the usage rights for all business purposes. We retain copyright for portfolio use only.

What equipment do you bring for on-site headshots?

We bring professional portable lighting (studio-quality results anywhere), seamless backdrops (neutral grey, white, or your branded colors), camera gear, and all necessary stands and modifiers. We handle all setup and breakdown. You just need to provide space—a conference room, office, lobby, or building exterior works perfectly.

Do you provide Certificate of Insurance for corporate headshot sessions?

Yes. We carry $1M general liability insurance and $1M professional liability insurance. COI certificates provided within 24 hours with venue-specific endorsements as needed. We're familiar with corporate building security and credentialing requirements.

Chicago Corporate Headshots & Team Portraits

Professional portraits that make
your team look as good as they are.

We come to you. Studio-quality results without the studio commute.

Half Day: $3,295 | Full Day: $6,500 | Teams Only

Request Team Quote

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Whatever Your Brand Needs, We Adapt

Not every company needs the same look. Our team brings the flexibility to shoot clean corporate headshots with neutral backgrounds, creative branding portraits with environmental context, or editorial-style imagery that showcases personality. Tell us your vision—we'll bring the lighting, backgrounds, and expertise to make it happen on-site.

Corporate Clean

Neutral backgrounds (white, grey, or branded), business attire, classic LinkedIn-ready headshots. Professional, polished, consistent across your team.

Environmental

Shot in your office, conference room, or building exterior. Natural light combined with pro lighting. Context that shows where you work, not just who you are.

Creative Branding

Editorial, personality-driven portraits for companies that want more than corporate. Styled, directed, and intentional—perfect for agencies, startups, and creative firms.

Recent Work — Corporate & Creative

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Team Headshot Days — Half Day or Full Day

Best for teams of 5+. We bring lighting and (requested) backgrounds to your office for efficient, professional headshot sessions.

Half Day

4 hours on-site

$3,295-$3,750

Professional portable lighting
Branded or neutral backgrounds
Efficient team photography
Professionally edited images
High-res digital files
Usage rights for business purposes

Full Day

8 hours on-site

$6,500-$7,500

Professional portable lighting
Branded or neutral backgrounds
Extended team photography
Multiple locations/setups if needed
Professionally edited images
High-res digital files
Usage rights for business purposes

📦 Delivery Timeline

Standard turnaround: High-resolution edited images delivered within 7 business days via private online gallery with download options.

Rush delivery available: 48-hour turnaround for urgent needs (additional fee applies).

What's Included: Premium Service Details

🎨 Professional Retouching

Skin smoothing, blemish removal, and color correction included. Natural, polished results—not over-edited.

💼 Full Licensing Rights

Use images for websites, social media, print materials, and marketing. You own the usage rights for business purposes.

💄 Makeup Artist Coordination

We can coordinate a professional makeup artist for your team (additional fee, arranged upon request).

🔒 $1M Insurance Coverage

Fully insured with COI certificates provided within 24 hours for venue requirements.

How Team Headshot Days Work

1

Consultation

We discuss your team size, style preferences (corporate, environmental, creative), background options, and scheduling.

2

We Come to You

Our team arrives with all equipment—lighting, backdrops, and camera gear. Minimal disruption to your workday.

3

Efficient Photography

We photograph your team members efficiently while maintaining quality. Natural direction, professional results.

4

Editing & Delivery

All images professionally edited and delivered within 7 business days (48-hour rush available). High-resolution files ready for LinkedIn, websites, and print.

Frequently Asked Questions

What's the 5-person minimum?

Our team headshot days are designed for companies with 5+ employees needing professional headshots. This ensures efficiency and makes the investment worthwhile for both parties. If you have fewer than 5 people, reach out and we can discuss options.

Do you only shoot corporate headshots, or can you do creative branding portraits?

Both! Our team adapts to your brand needs. We can shoot clean corporate headshots with neutral backgrounds, environmental shots in your office, or creative branding portraits with personality. Tell us your vision—we bring the flexibility to execute it.

Can you photograph executives in multiple looks?

Yes. We can photograph executives in multiple outfits, backgrounds, or settings within the same session. This is ideal for leaders who need different headshots for various platforms (LinkedIn, company website, conference bios).

Can you match our existing headshot style guide?

Absolutely. If you have an existing style guide or previous headshots you want to match, we can replicate lighting, framing, background, and editing style to ensure brand consistency across all team members—even if your original photographer isn't available.

Do you provide on-site tethering or live proofing?

Yes, we can set up on-site tethering so your team can see images in real-time during the shoot. This is especially helpful for executives who want to approve their look immediately or for teams that need quick image selection for urgent needs.

How long does each person's session take?

It varies based on the style you choose. Clean corporate headshots are efficient (5-10 minutes per person). Creative or multi-look sessions take longer (15-20 minutes per person). We'll discuss your needs during consultation and plan accordingly.

What equipment do you bring?

Professional portable lighting, backdrops (neutral or branded), and camera gear. We handle all setup and breakdown. You just need to provide space (conference room, office, building exterior—whatever works for your vision).

When will we receive the edited headshots?

Turnaround times are discussed during booking based on your team size and delivery needs. We'll provide a clear timeline before your session.

Can you match our company's branding?

Yes. We can shoot with your branded backgrounds, match your website's visual style, and ensure consistent lighting/framing across all team members. Perfect for creating a cohesive look for your About Us page or team directory.

Do you provide a Certificate of Insurance?

Yes. We carry $1M general liability insurance and provide COI certificates within 24 hours with venue-specific endorsements if needed.

Ready to Upgrade Your Team's Headshots?

Professional on-site headshot days for teams of 5+. Half day or full day available.