Weddings • Proposals • Engagements • Elopements
Chicago-Based • Midwest & Destinations
Chicago Wedding Photography — For couples who dance to their own love song.
Quiet Luxury • Cinematic • Non-Traditional
Creative. Soulful. Cinematic — a quiet luxury experience blending real connection, painterly light, and editorial calm.
- 48–72 hour highlights
- Inclusive & multicultural expertise
- Zero stiff posing
“Jeremy made our vision come to life—and even trekked through a forest to get the photos of our dreams.” — Alyssa & Danny
As Seen In / Trusted By
Why Couples Feel Relaxed With Me
With professional roots as an actor and director, I know both sides of the camera— guiding natural movement, reading energy, and pacing moments so you feel present (not posed).
- Calm, clear direction when you want it; quiet observation when it counts.
- Camera-shy friendly: gentle prompts that feel natural, never stiff.
- Cinematic storytelling: emotion first, trend-proof, creative portraits second.
It all starts with popping the BIG QUESTION: From intimate “yes” moments to all-day wedding celebrations — I capture every chapter of your story.
Chicago Proposal Photography
Chicago Proposal Photography — Artful. Discreet. Timed to the Minute.
One chance, perfectly planned. I scout the exact spot, lock timing to the minute, cue your position—then capture the “yes,” followed by elevated, artful portraits right after. Quality-first, never factory edits.
Led by a former actor/director for cinematic direction, real emotion, and zero stiff posing. Inclusive & sensory-friendly experiences for all.
From $750; most invest $850–$1,100. Highlights within 48–72 hours.
- 100+ ★★★★★
- Trusted at The Ledge & Chicago Winery
- Multicultural & LGBTQ+
Chicago Engagement Photography
Cinematic Engagement Portraits with Real Connection
Your engagement session should feel like you—clean color, painterly light, and direction that reads natural on camera. Editorial polish, human heart.
We plan locations and timing by light—neighborhood streets, skyline rooftops, or quiet gardens—and keep things relaxed with simple prompts (zero stiff posing).
Sessions from $750; most couples invest $850–$1,050. Expect 60–120 edited images in a private gallery.
As seen at Chicago Winery — a cinematic experience
Preferred Venue Partner
Chicago Winery Wedding Photography — Cinematic. Intimate. Unforgettable.
Chicago-based • Available across the Midwest & destinations worldwide
Warm light. Architectural texture. Electric connection. As a preferred vendor at Chicago Winery, I craft imagery that turns barrel rooms and candlelit receptions into cinematic scenes—tailored to your story.
Frequently Asked Questions
How much do couples typically invest?
Most wedding collections range from $6,500–$8,150 and include two photographers for full-day, cinematic coverage. Proposal sessions start at $750, and engagement sessions typically range from $750–$1,050—crafted to tell your story from the first “yes” to “I do.”
How fast will we see our photos?
You’ll receive a curated 48–72 hour highlight set for instant sharing. Full galleries follow on your promised delivery timeline—never rushed, always refined.
Do you help plan proposals and sessions?
Absolutely. From location scouting and timing-by-light to subtle coordination, I help design the experience so it unfolds naturally and beautifully.
Do you travel?
Yes. Chicagoland is included, and I regularly travel throughout the Midwest and beyond for destination weddings. Share your plans in the inquiry form for a tailored quote—wherever your story takes you.
We’re camera-shy. Can you help?
100%. My approach is comfort-first and direction-light—gentle prompts, no stiff posing. You’ll look and feel like yourselves, with genuine emotion and relaxed confidence.
How does your actor/director background help us?
I’ve spent years as both an actor and director, which means I know how to draw out authentic emotion, guide movement with empathy, and read energy in real time. You’ll feel relaxed, seen, and effortlessly directed—resulting in images that are cinematic, natural, and truly you.
For Couples Who Want More Than Tradition
Painterly light, true color, and honest emotion—photojournalistic in spirit, elevated in style. Weddings include two photographers for seamless coverage; proposals are planned to the minute with discreet execution.
Recent favorites: Lyric Opera, The Rookery, Ping Tom Park, Willis Tower Ledge, Gaelic Park, Lincoln Park Conservatory, Ella Elli. Every setting becomes a stage for thoughtful composition, luminous light, and authentic moments.
- Style: painterly, soulful, editorial polish—zero stiff posing
- Experience: inclusive & multicultural expertise; calm direction so you can be present
- Delivery: fast 48–72 hour highlights; curated galleries with print rights
Why Couples Choose Jeremy Glickstein Photography
Unmistakably You—Not a Template
We 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 our 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.
The Art Is in the Feeling
Every frame begins the same way — with light, breath, and intent — but ends with something entirely yours. This isn’t about stiff poses or fleeting trends. It’s about crafting images that move like memory and feel like truth.
If you’ve ever wanted photographs that look like *you* — luminous, cinematic, unapologetically alive — this is where that vision becomes real. Scroll on, and see how story, light, and emotion converge.
Quick Answers
How fast will we see photos?
48–72 hours for highlights. Full galleries follow per collection and timeline.
Do you travel beyond Chicago?
Yes—across the Midwest and for destination weddings. Share details for a tailored quote.
We’re camera-shy. Can you help?
Absolutely—comfort-first direction, zero stiff posing. Real moments, flattering guidance.
What Couples Say
Real notes from real celebrations—scroll for more.
Read 100+ Google reviews
— Jen & Kirill • The Rookery Building“Jeremy, thank you again for all your help and diligence, and for making our wedding day unforgettable! We couldn't be happier with how everything turned out, and we can't thank you enough for being there for us. We love the shots!”
— Kristine & Nick • River North & Chicago Winery“We couldn't be happier with our engagement photoshoot experience with Jeremy! He did an absolutely fantastic job capturing my fiancé Kristine and me in some of Chicago’s most iconic locations… Thank you for giving us memories we’ll treasure forever, Jeremy!”
— Carlos Frias (James Beard award-winning journalist) & Gaby • Skydeck, Willis Tower“Jeremy was a pro to work with. He scouted the location weeks in advance to set up a surprise shot and made use of every last minute of our time. He made some beautiful images — they speak for themselves!”
Cinematic Portfolio: Weddings, Proposals & Engagements
Painterly light and true-color portraits with honest emotion. Chicago settings from The Rookery to lakefront rooftops, suburban forests to West Coast ocean vibes. Signature Vision for couples who want more than tradition: cinematic, daring, unforgettable.
Two photographers on weddings • 48–72h highlights • Inclusive & multicultural experience
Cinematic. Inclusive. Comfort-First.
Many say “authentic.” I deliver cinematic, painterly storytelling that feels true to you—bold when you want it, quiet when you need it. Zero stiff posing.
Inclusive Chicago Wedding Photography
Love is love—every story deserves to be celebrated. LGBTQIA+-affirming, body-positive, neurodivergent-aware.
Offbeat & Creative
Star Wars vows, drag brunch receptions, roller-derby exits—bring the wild ideas. I’ll craft frames that feel like a film.
Stress-Free & Camera-Shy Friendly
Gentle direction, sensory-friendly pacing, and micro-prompts—so you can be present while I catch the in-between magic.
Cinematic Wedding & Proposal Reel
Our videography captures the same painterly light and soulful honesty as our photography — weaving vows, laughter, and fleeting moments into a cinematic story you’ll replay for decades.
Based in Chicago, we create wedding and proposal films with cinematic storytelling and painterly visuals. From intimate elopements to full-day celebrations, our videography blends natural sound, authentic emotion, and editorial polish — crafted to feel timeless and unforgettable.
Chicago Corporate Photography & Creative Headshots
When I’m not photographing weddings and proposals, I bring the same cinematic eye to corporate events, summits, and professional portraits. Because your work deserves imagery that feels alive, not stock.
👉 View Corporate Work:
Jeremy Glickstein Photography
Cinematic with Soul — For Couples Who Want More Than Typical Photos
I create cinematic, painterly photography with true color and honest emotion—photojournalistic in spirit, elevated in style. Proposals planned to the minute. Engagements timed by light. Weddings documented with two photographers, so nothing is missed.
48–72 hour highlights • Inclusive & multicultural expertise • Calm direction, zero stiff posing
Quick Answers (Logistics)
Practical details couples ask most—short, clear, and to the point.
What do we receive?
High-resolution JPEGs in a private online gallery with personal print rights. Easy sharing, downloads, and pro lab print options.
When do previews & galleries arrive?
Highlights in 48–72 hours. Full gallery timelines are set in your proposal & contract; rush options available on request.
How does booking work?
Simple e-contract + retainer to reserve your date. Flexible plans split the balance into 2–3 payments.
Weather & reschedules (proposals)
We plan light-by-time with a weather fallback. If conditions shift, we move to a covered or alternate spot and keep the moment stress-free.
Locations & permits
We’ll guide you on photo permits (parks, rooftops, landmark lobbies) and timing to avoid crowds. We handle scouting & logistics.
Albums & prints
Heirloom albums, framed prints, and parent books available à la carte or bundled. Design help included.