Chicago Wedding, Proposal & Event Photographer
Chicago Wedding & Event Photographer
A beautiful dream you can
revisit over and over again.
Comfort-based direction. No posing, just truth.
Let me show you how beautiful you are.
As You Wish151 Five-Star Reviews · Preferred vendor at Chicago Winery & Cuneo Mansion
Your Truth, Your Love - Painted with Light
From grand ballrooms to urban romantic scenes to quiet forests—as you wish
This Isn't for Everyone.
See If It's for You.
The most common comment I get from potential clients who end up working with me is that they became overwhelmed in their wedding photographer search before finding me. Most of the photographers they looked at had had nice images, but they all looked the same and trendy. Then they found my work and the "AHA" moment happened. They finally found someone who was doing something cinematic, creative and different-in the best possible way, but still rooted in truth.
Half of my clients crave amazing photos but feel awkward being photographed and need someone to guide them. The other half are more outgoing — they want beautiful, unique images (sometimes with wild or offbeat themes) but can't find the right person who can deliver the BIG 3: comfort, creative vision, and outstanding images. In either case, it's a hug and love fest upon my departure from their wedding reception. And once the highlights arrive, they can't stop looking at themselves.
This is by design. I spent 10+ years as a professional actor and acting coach — including work at Steppenwolf Theatre Company and a Jeff Award (Chicago's Tony equivalent). I learned how to help people relax, be present, and reveal their beauty while helping to shape a unique story. My years as a fine art street photographer enhance the experience, making me able to quickly find where we need to be for the best pictures. All I ask of you is to be willing to take a little chance, show up and be in love.
You'll forget the camera exists. Then you'll see photos that take your breath away.
How It Works
From first call to final gallery — a process designed to bring out your best.
I Learn Your Story
I talk about your vision, your comfort level, what makes you nervous, and what you ultimately hope to see in your collection — it's a creative collaboration where you're the star and I'm your guide.
Your Vision Takes Shape
I create a loose vision based on your must-haves and my creative instincts. Think: "golden hour in the forest," not "pose #47." I adapt spontaneously to your energy throughout the day — I capture your requests and co-create other gems along the way.
You Forget I'm There
I guide you with natural prompts — never stiff poses. You'll feel like you're alone together, not performing for a camera. The magic happens when you forget the camera exists.
You See Yourself
48-72 hour highlights in your inbox. Full gallery in 3-5 weeks. You're not waiting months to relive your day — you're sharing breathtaking images with family and friends immediately.
"Jeremy treats the session as a casual hang that allows any anxiety to melt away. It was an absolute joy to walk around and spontaneously snap pictures when he found a nicely lit nook or environment. The finished product was perfection." — Jason Babinsky
151 Five-Star Reviews Across:
The Moments Before "I Do"
Where Love Stories Begin
The Moment Everything Changes
Hidden until the ring appears. Present for every tear of joy after. From Skydeck surprises to intimate lakeside questions—cinematic coverage that disappears until you need it.
View Proposal Photography →Celebrate the Beginning
Relaxed, editorial sessions that feel like a date — not a photoshoot. You'll forget the camera exists. That's when the real magic happens.
View Engagement Photography →Trusted by couples who want to feel like themselves and crave creative vision
Chicago Wedding Photography
As a former Chicago theater actor (credits include Steppenwolf Theatre Company), director and acting coach with 10+ years of experience, I learned something invaluable: people reveal their authentic selves when they feel comfortable and forget they're being watched. That's exactly what I bring to your wedding day—gentle guidance that helps you relax, connect, and be yourselves while I capture the beauty you create naturally. With preferred vendor status at Chicago's most exclusive venues including Chicago Winery, camera-shy couples trust me to help them feel at ease. Lives of the party welcome me as their ultimate hype man. Every wedding includes two photographers, 48-72 hour highlights, and hand-edited galleries that look and feel like a dream.
Chicago Proposal Photography
From the Skydeck to the Riverwalk, Lincoln Park to North Avenue Beach, I specialize in capturing surprise proposals with cinematic precision and complete discretion. Every proposal is meticulously planned—location scouting, timing by light, hidden positioning—so the moment unfolds naturally while I capture every genuine emotion. Last-minute requests welcome—I accommodate proposals with as little as 48 hours notice.
Begin Planning Your Proposal →Chicago Engagement Photography
Engagement sessions are where couples fall in love with my process—painterly light, calm guidance, and zero awkward posing. We'll explore Chicago's most photogenic neighborhoods or your favorite hidden spots, creating editorial portraits that feel authentic and effortless. Camera-shy couples especially appreciate my actor-trained approach to natural movement and genuine connection. Sessions include 50-75 edited images and a complimentary location consultation.
Reserve Your Session →Corporate Headshots Chicago
Editorial-quality executive headshots and team photography for Chicago's top companies. From individual LinkedIn profiles to full team galleries, we bring the same cinematic approach to corporate photography—professional polish with human warmth. My team of associate photographers can accommodate 10-200+ employees in a single day with on-location sessions at your office, consistent editing across your entire team, and fast turnaround (5-7 business days standard, same-day rush available). Law firms, tech companies, and creative agencies trust us for headshots that don't look corporate.
Corporate Event Photography Chicago
Conference coverage, product launches, team celebrations, and annual galas documented with editorial sophistication. We capture candid moments, keynote presentations, and networking interactions that tell the story of your event—not just documentation, but compelling visual narratives your team will actually want to share. Available for half-day or full-day coverage throughout Chicagoland, with same-week highlight delivery for time-sensitive marketing needs. My team can cover multiple simultaneous events when needed.
📞 I respond within 2 hours • Same-day consultations available
Why Couples Choose Jeremy Glickstein Photography
Unmistakably You—Not a Template
I build around your story and aesthetic so the work feels singular. Editorial polish, human heart—never cookie-cutter.
Calm Direction, Real Moments
Camera-shy friendly. Natural direction that looks effortless on camera, with space for genuine emotion.
Two Photographers, Every Angle
Seamless coverage with quick highlights and confidence in any venue, any light.
Editorial Polish, Human Heart
Authentic moments, elevated with intention. See my Chicago engagement sessions for real examples.
Fearless & Inclusive
Bold vision with honest emotion—LGBTQ+, interfaith, and multicultural celebrations welcome.
Painterly Backdrops
Urban romance to dreamy gardens—timed by light and tailored to you. Explore a recent Chicago proposal.
Questions You're Probably Thinking
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 with the same cinematic quality—every image still edited by Jeremy.
Proposals: $750–$1,100
Engagements: $750–$1,050
How fast will we get photos?
Highlights: 24–72 hours depending on collection—perfect for sharing before you've even opened thank-you cards.
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. Here's why it won't be awkward:
I spent 10+ years as a professional actor, director, and acting coach—including work at Steppenwolf Theatre Company and a Jeff Award. I learned how to help people feel comfortable on camera, then taught other actors to do the same.
So instead of "smile at the camera," I give you something real to do. Walk toward each other. Whisper something that makes you laugh. 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. The vulnerability, the self-consciousness—I've been there. That empathy shapes how I guide you.
2. I read energy and adapt. Improv training. If you're nervous, I slow down. If you're energized, I match it. No rigid shot list—just responsive, intuitive direction.
3. I find the moments. Years of directing taught me to see what others miss—the glance, the squeeze, the laugh that tells the real story.
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'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, same editing style—because I edit every single gallery myself, regardless of who shot it. $5,500–$7,750.
Both deliver the cinematic, painterly look you see in my portfolio. The difference is who's behind the camera, not the quality of the final images.
Our venue has terrible lighting. Is that a problem?
No. I thrive in low light.
Professional gear (Canon EOS R3 & premium lenses), mastery of ambient light, and years of shooting in dark churches, candlelit receptions, and nighttime ceremonies. When needed, I bring subtle professional lighting your guests won't even notice.
If a photographer can't confidently answer this question, think twice about hiring them.
Our venue isn't very photogenic. Can you still make it look good?
There are no boring venues—only boring photographers.
I've shot weddings in church basements, suburban backyards, hotel conference rooms, and city parks. Created stunning work in every one. 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 so you can share the news immediately.
Last-minute requests welcome—I accommodate proposals with as little as 48 hours notice.
How does booking work?
Simple: e-contract + retainer secures your date. Payment plans available (50/50 or split into thirds). Final balance due one month before your wedding.
I handle all logistics and coordination from there.
What exactly do we receive?
Highlights: 24–72 hours post-wedding
Full gallery: 500–700+ hand-edited images (weddings)
Files: High-resolution digital downloads with full print rights
Sharing: Private online gallery for easy sharing with family
Prints: Available through your gallery's integrated print shop
What if it rains?
We plan for it. Every session includes weather fallbacks. If conditions shift, we adapt—covered locations, dramatic rainy-day shots, or reschedule if needed.
Some of my favorite photos have come from "bad" weather days. Overcast light is gorgeous. Rain creates drama. Trust me.
Do you handle permits and logistics?
Yes. I guide you on permits (parks, rooftops, landmark lobbies), optimal timing to avoid crowds, and venue coordination. All scouting and logistics handled in advance.
What if something goes wrong?
I carry professional liability insurance, bring backup equipment to every shoot, and have relationships with top Chicago venues who trust me to handle anything.
In 200+ weddings, I've never missed a moment. But if something did happen, you're protected.
Beyond the Wedding Day
Corporate Photography That Doesn't Feel Corporate
Headshots • Events • Branding • Food
When I'm not photographing weddings, I'm behind the lens for Chicago's most discerning companies—from intimate executive portraits to full-day team headshot sessions to black-tie galas for Fortune 500 clients. The same theater-trained approach that helps camera-shy couples relax works just as well on camera-shy executives. Same cinematic quality. Same hand-edited finish. Just a different kind of milestone.
