Chicago Proposal & Wedding Photographer | Jeremy Glickstein Photography
If you're reading this, you care about the details as much as I do.
Chicago Proposal & Wedding Photographer
A beautiful dream you
can walk back into.
Hand-edited, cinematic proposal & wedding photography. From the question to the vows. Permission to be yourselves.
Planning a wedding? Start here
300+ Proposals Captured · 250+ Weddings · 151+ Five-Star Reviews · Preferred at Chicago Winery
Jeremy Glickstein is a Chicago wedding, proposal, and engagement photographer based in Highland Park, serving Chicago, the North Shore, and destinations worldwide. With a decade of professional theater experience, including work at Steppenwolf Theatre Company and a Jeff Award, he brings confident, reassuring guidance that helps camera-shy couples forget the camera exists, and the creative vision to pull off bold ideas other photographers won't attempt. Film-like images. Wedding and proposal galleries hand-edited personally by Jeremy, never outsourced.
151+ five-star reviews · Preferred vendor at Chicago Winery · Fearless Photographers · WPJA · Best of Zola 2025 & 2026
Proposals
300+ Chicago proposals since 2019. Full planning partnership: location, timing, signal, and execution. Theater-trained guidance for the moments after the "yes."
Explore Proposal PhotographyEngagements
Cinematic portraits that feel like you. The best practice you'll ever get.
Explore Engagement SessionsWeddings
Story-driven coverage with two photographers on every wedding. Gentle guidance that lets you forget we're there.
Explore Wedding CollectionsHere for business? Corporate events and team headshots
Before you ever show up
The part most photographers skip.
The moment cannot be redone, so I plan it like it cannot be redone. By the time you arrive, the hard parts are already solved. Here is what I have handled before you take a single step.
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Location scouted for your exact time
I know how each spot photographs at the hour you will be there, where the light falls, and which angle keeps the background clean. Not a guess on the day.
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Sunset timed to the minute
We build the plan around the light, not the other way around. You get the window where the city looks like a film still, and we work back from it.
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Permits and crowds handled
Some Chicago locations need a permit. Others have crowd patterns that make a hidden position nearly impossible at the wrong hour. I tell you which is which before you commit to a spot.
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A hidden position and a clean reveal
I plan exactly where I will be so I stay invisible until the ring appears, and a signal so I know the moment you are in position. You are never improvising.
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A weather backup that actually works
Every plan includes a real pivot: a covered alternative, a shift in timing, or a clean reschedule at no extra cost. Rain never gets to decide how this goes.
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Simple signals for the day
Two quick texts, a clear cover story, and a plan you can actually remember while your heart is going. The logistics disappear so you can be present.
Most couples plan this from out of state. I handle the Chicago side so nothing is left to chance. Start your plan
Recent proposal North Avenue Beach + Lincoln Park
Miguel & Ally
Miguel reached out from out of state to propose in a city neither of them was from. The disguise wrote itself: Ally had just graduated, so the afternoon became a skyline graduation shoot, right up until it became the question. We spent the first fifteen minutes letting her settle and forget the camera, so the yes landed when she was comfortable, not braced.
We built the timing around the light and moved across two locations as the sun dropped: the iconic skyline frame at the beach, then a softer, painterly golden hour at the South Pond boardwalk. The frames they loved most were the unplanned ones, the two of them lying in a field of dandelions on the walk back.
Read the full story"Thank you for being so amazing and allowing us to be ourselves."
Miguel, the morning after the gallery delivery
Chicago's proposal specialists
The proposal is where the whole story starts.
Three hundred plus proposals since 2019, and I have never run the same one twice. This is the work I am known for: discreet, planned to the minute, and warm enough that the portraits after the yes feel like the two of you, not a photo shoot.
Most couples plan from out of state. I handle the Chicago side: location, light, permits, hidden positioning, and a weather backup that actually works.
Planning from out of state? Here is how it works. · Need someone this week? Last-minute proposals.
Blueprint
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.
Saving Grace
Most couples tell me the same thing: they were drowning in the photographer search. Everyone's work looked the same. Trendy. Nice enough. Forgettable. They wanted something different. And then they found me.
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 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
151+ Five-Star Reviews Across:
From the question to the vows
When the proposal becomes a wedding.
For most of my couples, the proposal is chapter one. By the wedding day the nerves are gone and you already have a photographer who knows how you move, how you laugh, and how you are with each other. Every wedding includes two photographers, highlights in 24 to 72 hours, and a gallery hand-edited personally by me.
Every collection is customizable. Tell me what your day looks like and we will build the right fit.
Questions You Likely Have
How much do couples typically invest?
Proposals: three collections at $795, $895, and $985. Most couples invest $895 to $985 depending on time and locations. The Cinematic, with two photographers capturing the moment from two angles, is $1,795.
Weddings: three collections at $5,975 (8.5 hours), $6,750 (9.5 hours), and $7,500 (10.5 hours). Two photographers are included on every wedding. Most couples book the middle collection. Every collection is customizable.
How fast will we get photos?
Wedding highlights: 24 to 72 hours, perfect for sharing before you've even opened thank-you cards.
Wedding full gallery: 3 to 5 weeks, hand-edited personally by me. Never rushed, never outsourced.
Proposal highlights: 48 to 72 hours.
Proposal full gallery: 5 to 7 days. See examples in my portfolio.
We want great photos but we are self conscious about not looking good. Will this be awkward?
About half my couples say exactly this. Here's why it won't be awkward:
I spent 10+ years as a professional actor, acting coach, and director (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 background as an actor and director 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 guidance that feels natural, never theatrical.
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.
Who will photograph our wedding?
Depending on your date and preferences, you'll work with either me or one of my personally selected and trained associate photographers. Two photographers are included on every wedding, and either way, I edit every single wedding gallery myself. That's how the cinematic, painterly look stays consistent across every wedding we shoot.
On our call, I'll let you know who's available for your date and we'll find the right fit together. Let's talk.
How do proposal sessions work?
I handle everything: full planning partnership covering location, timing, cover story, and signal coordination. Pre-scouted angles, hidden positioning, and gentle guidance from a former actor and acting coach for the comfortable portraits after the "yes."
Highlights delivered within 48 to 72 hours so you can share the news immediately. Full hand-edited gallery within 5 to 7 days.
Last-minute requests welcome. I accommodate proposals with as little as 48 hours notice. Learn more about proposal photography.
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. 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 in church basements, suburban backyards, hotel conference rooms, and city parks. Created work I'm proud of 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. See a recent venue showcase.
Do you travel for weddings?
Yes: Chicagoland, the Midwest, and destination weddings worldwide. Travel fees apply outside the Chicago area. Share your plans and I'll send a tailored quote.
What venue are you a preferred vendor at?
I'm a preferred vendor at Chicago Winery, meaning the venue trusts me enough to recommend me to their couples. I've photographed many weddings there and know exactly where the best light falls at every hour. See Chicago Winery work.
Do you photograph LGBTQ+ weddings?
Absolutely. Love is love. LGBTQ+ weddings are celebrated here, not just tolerated. I'm proud to be listed on Equally Wed and have photographed many same-sex weddings and celebrations across Chicago.
How does booking work?
Simple: an e-contract and retainer secure 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 to 72 hours after the wedding
Full wedding gallery: 500 to 700+ images, hand-edited personally by me
Files: high-resolution digital downloads with full print rights
Sharing: a 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 a weather backup. If conditions shift, we adapt: covered locations, dramatic rainy-day shots, or a reschedule if needed.
Some of my favorite photos have come from "bad" weather days. Overcast light is gorgeous. Rain creates drama.
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 Chicago venues who trust me to handle anything. Across 250+ weddings and 300+ proposals, I've never missed a moment. But if something did happen, you're protected.
For companies and teams
Corporate photography that runs on time.
The same guidance that helps a camera-shy couple relax works just as well on a camera-shy executive. Group headshots, conferences, summits, and galas across Chicagoland, with dependable logistics, consistent editing, and fast turnaround at scale.
Group & Team Headshots
On-location sessions for teams of 10 to 200+ in a single day. Consistent lighting, consistent editing, every employee looking like the best version of themselves. Built for offices, summits, and conferences.
- Teams of 10 to 200+
- On-location throughout Chicagoland
- Rush delivery available
Events, Summits & Galas
Conference coverage, product launches, fundraisers, and annual galas. Photos your marketing team will actually use and your people will actually share. Same-week highlights for time-sensitive campaigns.
- Same-week highlights
- Multi-event coverage
- Net 30 invoicing
