Chicago headshots
that actually look
like you.
You're accomplished, credible, and confident in real life. Your headshot should say the same thing. A guided, professional experience fifty-one floors above Streeterville, with the city behind you.
Morning
America
Magazine
Magazine
Lifestyle
Your headshot
isn't doing you
any favors.
You know you should update it. You think about it every time you visit your LinkedIn profile or send someone to your website. But somehow the right moment never comes.
- Years out of date, it simply doesn't look like you anymore
- Stiff or awkward, not really capturing your personality
- A casual photo that doesn't match your professional level
- Something you quietly apologize for when you share it
The problem isn't how you look. It's that most headshots are taken without real direction, thoughtful lighting, or a process designed to help you feel at ease. That's exactly what the Headshot Marathon is designed to fix.
Same polished headshot.
Your choice of backdrop.
Choose a clean studio background like this one, the Chicago skyline softly out of focus behind you like the photo at the top of the page, or a mix of both. Every image is framed three-quarter length, which gives you room to crop in for LinkedIn, your website, or your speaker bio.
Fifty-one floors up,
in the middle of it all.
The Chicago studio is in Streeterville, steps from the Magnificent Mile. Easy to reach from River North, the Loop, and the Gold Coast, and simple for out-of-town clients staying downtown.
Studio 25 Chicago
220 E. Illinois St
Chicago, IL 60611
Park at the City Front garage next door or take the Red Line to Grand. Full check-in details come with your booking confirmation.
Closer to the suburbs?
The same headshot experience is available at Studio 25 in downtown Naperville, with easy parking.
See the Naperville headshot pageHere's how
it works
Before Your Session
You'll receive an outfit and prep guide ahead of your session so you arrive knowing exactly what to wear and what to expect. No guessing, no last-minute outfit panic. Just confidence from the moment you walk in.
Your Studio Session
You'll start with a makeup touch-up so you feel camera-ready, then our team guides you through natural poses and expressions in front of the studio backdrop or the city window. Plan for about an hour in the Chicago studio, including a 30-minute guided shoot and time to choose your favorites.
Same-Day Selection
You review and select your favorites before you leave. Your final retouched images are delivered within 72 hours, ready to update LinkedIn, your website, or anywhere you show up professionally.
No surprises.
Just results.
Outfit & Prep Guide
Know exactly what to wear and how to prepare so you walk in feeling confident, not stressed.
Makeup Touch-Up
A camera-ready refresh that enhances your natural look without overdoing it. Polished and like yourself.
30-Minute Guided Shoot
Up to 4 outfit changes with expert direction throughout, as part of about an hour in the studio.
Same-Day Image Selection
Review your images in person and choose your favorites before you leave. Nothing left to chance.
Two Retouched Images
Professionally edited and delivered within 72 hours. Ready to use everywhere you need to show up.
Expert Direction
Guided posing and expression coaching so you always know how you're coming across on camera.
Additional images available at $250 each. You only purchase what you love.
Simple, transparent
pricing
Reach out and we'll find a time that works for you at Studio 25 Chicago. If something more custom fits you better, we'll talk that through too.
$550
Outfit and prep guide
Professional makeup touch-up
About an hour in the studio
30-minute guided shoot · up to 4 outfits
Same-day image selection
Two final retouched images · delivered within 72 hours
Led by Emily Cummings.
15 years of helping people
feel at ease on camera.
Headshots can feel surprisingly vulnerable, because they're not just photos. They're how you introduce yourself to clients, colleagues, and opportunities before you ever say a word.
Most people arrive a little nervous. That's completely normal. Over hundreds of sessions, our team has learned that the right direction, lighting, and pace make all the difference. By the time you're selecting your images, most clients are surprised by how much they love what they see.
Emily started her career in Chicago, and it's exciting to be back in the city, alongside the studio in downtown Naperville.
Schedule a CallReal Results. Real People.
Frequently asked
What if I'm not photogenic?
Almost everyone says this before their session, and almost no one says it after. You're guided through every expression and pose in real time, so you always know how you're coming across. The challenge for most clients ends up being choosing between too many good options.
Can I have the Chicago skyline behind me?
Yes. You can choose the clean studio backdrop, the city window with the skyline softly out of focus behind you, or a mix of both. Either way, your headshots are framed three-quarter length, from about mid-thigh up, so you have room to crop in exactly how you need for LinkedIn, your website, or print.
Can we do full-length photos or shoot around the city?
Full-length images, multiple locations around the city, and lifestyle photos are part of a branding session, which is planned separately. It's one of our favorite things to shoot in Chicago, so reach out and we can talk through it.
Who takes the photos?
Sessions are photographed by a member of our team, led by Emily Cummings. Every session follows the same studio lighting, direction, and retouching standards, so the experience and the quality are consistent no matter who is behind the camera. If you'd like to request Emily specifically, just ask.
How many outfits can I bring?
Up to 4 outfit changes are included. Our outfit and prep guide will help you choose pieces that photograph well and feel like you. Two retouched images are included, and many clients add more so they have a favorite from each look.
How long does the session take?
Plan for about an hour in the studio. That includes your makeup touch-up, a 30-minute guided shoot, and time afterward to choose your favorites.
Where is the Chicago studio?
The studio is at 220 E. Illinois St in Streeterville, steps from the Magnificent Mile. Park at the City Front garage next door or take the Red Line to Grand. Full check-in details come with your booking confirmation.
Do you have a Naperville studio too?
Yes. Studio 25 in downtown Naperville offers the same headshot experience. You can see the Naperville headshot page here.
What if I want more than 2 images?
That happens a lot. Additional images are $250 each, or you can purchase 4 images for the price of 3 if you decide on the day of your session. You select exactly which images you want edited. Nothing is saved afterward, so your selections are final.
What if I need a different day or something more custom?
Reach out and we'll look at other options together. The same goes if you're looking for a branding session, lifestyle photos, or a team shoot.
Every session is
designed around
you.
Whether you need images for LinkedIn, your website, speaking engagements, or press features, we create headshots that reflect your real credibility and confidence.
Your next chapter deserves
a headshot that keeps up.
Reach out, tell us a little about what you need, and we'll take care of the rest.
Let's get
you scheduled.
Fill out the form below and our team will be in touch within 24 hours to find a time that works and answer any questions.
