Chicago Wedding, Proposal & Engagement Photographer — Jeremy Glickstein Photography
If you're reading this, you care about the details as much as I do.
Chicago Wedding, Proposal & Engagement Photography
A beautiful dream you
can walk back into.
Cinematic. Hand-edited by me, never outsourced. Camera-shy? You'll forget I'm there. Creative visionary? I'm all in.
151 Five-Star Reviews · 18 Weddings/Year · Preferred photographer at Chicago Winery
Proposals
Quiet planning. Invisible until the ring comes out. Real emotion captured.
Explore Proposal PhotographyEngagements
Cinematic portraits that feel like you. The best practice you'll ever get.
Explore Engagement SessionsWeddings
Story-driven coverage with calm, confident direction. You forget I'm there.
Explore Wedding CollectionsBlueprint
We Talk
You tell me what you're dreaming of. I'll meet you there - then we'll make it better than you dreamed of.
I Prepare
Light, location, timing. You just show up and be in love.
You Forget I'm There
That's when it clicks. Then you see the photos and wonder who those people are.
Are you here because...
"We feel awkward on camera and need someone who actually gets it."
Nearly 50% of my couples start here. I spent 10+ years as an actor and acting coach, learning how to help real people relax on camera. No stiff poses. No forced "cheese." I give you something real to do, and you forget I'm there. That's when it works.
How it works →"We have a vision. And we need someone wildly creative to pull it off."
You're the "what if we did something completely different?" couples. The ones with Pinterest boards that scare other photographers. Fairytale forests. Industrial lofts. Something nobody's ever tried. This is what I'm here for.
See the work →"Honestly? We're both."
Maybe you're introverts who are also massive Star Wars fans. Maybe you want romantic and cinematic. That's not a contradiction. That's most of my favorite couples. Comfort and bold creativity aren't opposites. That's the whole point.
This Might Be Exactly What You Are Looking For.
Most couples tell me the same thing: they were drowning in the wedding photographer search. Everyone's work looked the same. Trendy. Nice enough. Forgettable. Then they found something different.
Half my clients want stunning photos but feel awkward being photographed. They need someone who can guide them without making it weird. The other half are bolder: they have creative visions, sometimes wild ones, and need someone who can actually pull them off. Both types leave the reception feeling like they just worked with a friend. And when the highlights land in their inbox, they can't believe that's them.
This didn't happen by accident. I spent ten years as a professional actor and acting coach. Steppenwolf Theatre Company. A Jeff Award (Chicago's Tony equivalent). I learned how to help people relax, be present, and stop performing. Nine years of fine art street photography trained my eye to find the right light and the right moment, fast.
All I ask is that you show up willing to take a small chance. Be in love. Let me handle the rest.
You'll forget the camera exists. Then you'll see what that looks like.
"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
150+ Five-Star Reviews Across:
Why Our Galleries Have Depth
Most photographers squeeze portraits into 10 rushed minutes between ceremony and cocktail hour. You get a few standard poses, maybe one "candid" moment, then you're whisked away.
I protect 25-45 minutes for an unhurried portrait session: time to settle in, find the light, and actually make something. Not just document it.
For couples who want to go all out, extended sessions up to an hour let us explore multiple locations, wardrobe changes, or more elaborate creative concepts.
This is why couples who prioritize photography choose to work with me. The extra time isn't a luxury. It's the difference between "nice photos" and images you'll actually want to hang.
for portraits
for extended sessions
Before the Dress, Before the Aisle
Before the Wedding
Invisible Until the Ring Comes Out
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 →The Best Practice You'll Ever Get
Relaxed, editorial sessions that feel like a date, not a photoshoot. You'll forget the camera exists. That's when the best shots happen.
View Engagement Photography →
Chicago Wedding Photography
I spent 10+ years as an actor and director (including Steppenwolf Theatre), learning how to help people feel comfortable enough to forget they're being watched. That's what I bring to your wedding. Every wedding includes two photographers, 48–72 hour highlights, and hand-edited galleries that look and feel like a dream. Preferred vendor at Chicago Winery & Cuneo Mansion.
Chicago Proposal Photography
From the Skydeck to the Riverwalk, I specialize in capturing surprise proposals with cinematic precision and complete discretion. Location-scouted, timed by light, photographed from hidden positions. I'm in place before you arrive, invisible until after the "yes." Last-minute requests welcome. I've orchestrated proposals with 48 hours notice.
Plan Your Proposal →Chicago Engagement Photography
This is where most camera-shy couples realize: "Oh, this isn't going to be awkward." Painterly light, calm guidance, zero awkward posing. We'll explore Chicago's most photogenic spots or your favorite hidden corners. We enter the wedding day not as strangers, but as co-conspirators. Sessions include 50–75 edited images and a complimentary location consultation.
Book Your Session →Corporate Headshots Chicago
Editorial-quality executive headshots and team photography. Same cinematic approach, professional polish with human warmth. My team can accommodate 10–200+ employees in a single day with on-location sessions, consistent editing, and fast turnaround. 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, annual galas. Not just documentation: compelling visual narratives your team will actually want to share. Same-week highlight delivery for time-sensitive marketing. My team can cover multiple simultaneous events.
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 guts. Never cookie-cutter. See the difference in my portfolio.
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 48-72 hour highlights and confidence in any venue, any light.
Polished but not stuffy
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. Read what couples say.
Painterly Backdrops
Urban romance to dreamy gardens, timed by light and tailored to you. Explore a recent Chicago proposal or see the Chicago Winery showcase.
Questions You Likely Have
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. See examples in my portfolio.
We want great photos but we are self conscious and feel a little scared about not looking good. Will this be awkward?
About 50% 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. Learn more about my background.
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 it clicks.
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. See what couples say about the experience.
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. View all wedding collections.
Our venue has terrible lighting. Is that a problem?
No. I thrive in low light.
Professional gear (Canon EOS R3 and 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. See examples from challenging venues in my portfolio.
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. Watch what happens. See a recent venue showcase.
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. Learn more about proposal photography.
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. Check your date's availability.
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 300+ 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.
