Chicago Wedding, Proposal & Event Photographer
Chicago Wedding & Event Photographer
A good dream that you can
revisit over and over again.
No posing. Sincerity and light will paint your pictures.
No matter who you are, you are beautiful.
As You Wish149+ Five-Star Reviews · Preferred vendor at Chicago Winery & Cuneo Mansion
Every Love Story, Rendered in Light
From grand ballrooms to quiet forests—your story, wherever it unfolds
Why Camera-Shy Couples Feel Comfortable With Jeremy Glickstein Photography
Most couples feel awkward in front of a camera. I help you feel comfortable.
Here's why: 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 authentic selves. Now I bring that same skill to every wedding.
I don't pose you stiffly. I guide you gently—and you forget the camera exists.
"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
How I Help You Look & Feel Amazing on Camera
Years of performing and coaching taught me how to draw out real emotion and connection — so your images feel like an authentic reflection of you, not a staged version.
Pre-Production Call
We talk about your vision, your comfort level, and what makes you nervous. I scout locations if needed. This isn't an intake form — it's a creative collaboration where YOU are the star and I'm your guide.
Custom Shot List
We create a loose shot list based on your must-haves and my creative instincts. Think: "golden hour portraits in the forest," not "pose #47." I adapt spontaneously to YOUR energy throughout the day.
Gentle Guidance on Your Day
I guide you with natural prompts and interactions — never stiff poses. You'll feel like you're alone together, not performing for my camera. Camera-shy couples especially love this approach.
48-72 Hour Highlights
The best 20-30 shots in your inbox within 48-72 hours. Full gallery in 2 weeks. You're not waiting months to relive your day — you can share highlights with family immediately.
Why Camera-Shy Couples Feel Comfortable
- Gentle guidance when you want it; quiet observation when it counts.
- I adapt to YOUR energy — my improv training means I read the room and adjust in real-time.
- You're not performing for my camera — you're living your day while I capture the beauty you create naturally.
- 10+ years of professional on-camera experience means I know exactly how to help you relax. View my IMDb profile.
What Couples Say
Real notes from real celebrations
— 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!"
149 Five-Star Reviews Verified 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 — not like they're posing for a camera.
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 149 five-star reviews and 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. I accept only 15 weddings per year—secure your date before availability closes.
View Wedding Collections →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—we accommodate proposals with as little as 48 hours notice.
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. Our 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. Our team can cover multiple simultaneous events when needed.
📞 We respond within 2 hours • Same-day consultations available
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.
Frequently Asked Questions
How much do couples typically invest in wedding photography?
Most wedding collections range from $7,000–$9,500 and include two photographers for full-day, cinematic coverage with 48-72 hour highlights. Proposals start at $750; engagements are $750–$1,050.
How fast will we see our wedding photos?
You'll receive 48–72 hour highlights perfect for sharing with family and vendors. Full galleries follow on your promised delivery timeline—never rushed, always refined.
Do you help plan proposals and sessions?
Yes. Location scouting, timing-by-light, and subtle coordination so it unfolds naturally and beautifully. I stay hidden during proposals and capture every genuine emotion.
Do you travel for weddings?
Yes—Chicagoland, Midwest, and destination weddings worldwide. Share your plans for a tailored quote. Travel fees apply for destinations outside the Chicago area.
We're camera-shy. Can you help?
Absolutely—and you're in excellent company. Most couples feel this way, even professional actors I've worked with during my 20+ years at theaters like Steppenwolf Theatre Company.
I'm a Jeff Award-winning actor and professional acting coach (view my IMDb profile). I spent decades learning how to be natural in front of cameras, then coached other actors through the same anxieties.
Here's my approach: I don't pose you stiffly or make you perform. I gently guide you through natural movements—walking hand-in-hand, whispering something sweet, laughing at an inside joke. My improv training means I adapt spontaneously to YOUR energy and comfort level.
You're the star. I'm your shepherd, helping you relax into the most beautiful, authentic version of yourselves.
How does your 20+ years as a professional actor and acting coach help us?
After 20+ years performing professionally—including at Steppenwolf Theatre Company and earning a Jeff Award—I became a professional acting coach, teaching actors how to be natural on camera, move authentically, and stay present.
That entire toolkit is now in service to YOU on your wedding day:
• My improv training helps me adapt spontaneously to your energy—I read the room and adjust in real-time
• My coaching experience helps me gently guide you to be your most comfortable, authentic self
• My on-camera background means I know exactly how it feels to be vulnerable in front of a lens—and how to move past that anxiety
• My creative eye finds sublime moments and painterly light instinctively
You're not performing for my camera. You're living your day while I use my experience to help you relax, be present, and shine naturally. The result FEELS like a beautiful dream—but the process feels like hanging out with a friend who happens to have a camera.
View my IMDb profile • Read my full bio
What do we receive after our wedding?
48-72 hour highlights, full edited gallery (typically 500-700 images for weddings), high-resolution digital files with print rights, and an online gallery for easy sharing with family and friends.
How does booking work?
Simple e-contract and retainer secure your date. Flexible payment plans available (2-3 installments). Final balance due before your wedding day. We handle all logistics and coordination.
What about weather and reschedules for proposals?
We plan with weather fallbacks. If conditions shift, we move to a covered or alternate spot quickly. The moment stays stress-free and perfectly captured.
Do you handle photo permits and location logistics?
Yes. We guide you on permits (parks, rooftops, landmark lobbies), timing to avoid crowds, and venue coordination. We handle all scouting and logistics in advance.
Are albums and prints available?
Yes, via the user-friendly, online shop. High quality prints and other products.
Our church/venue has extremely low light. What do you do?
I thrive in low light. Professional-grade gear (Sony A1, fast glass), mastery of ambient light, and years of experience shooting in churches, candlelit receptions, and nighttime ceremonies mean I never compromise on quality—even in the darkest spaces.
When necessary, I bring professional lighting that's subtle, unobtrusive, and beautifully balanced. Your guests won't notice it, but your photos will glow.
If a photographer cannot confidently answer that question, think twice about hiring them.
We're worried our venue is too boring for cool photography. What do you do?
Here's my philosophy: There is no boring venue or street, only boring, unimaginative photographers.
I've shot weddings in church basements, suburban backyards, hotel conference rooms, and city parks—and created stunning, painterly work in every single one. My theater director training taught me to find beauty in unexpected places, work with available light, and turn constraints into creative opportunities.
Your venue becomes a canvas. I find the light, the angles, the textures, the fleeting moments that transform ordinary spaces into cinematic frames. Trust the process—your "boring" venue will look anything but boring in your gallery.
We love your work but you're not available on our date. Can you recommend other photographers?
Absolutely. I work with a curated team of exceptional photographers who share my cinematic, painterly approach. Each has been personally vetted for technical skill, artistic vision, and client care.
If I'm unavailable, I'll introduce you to one of our lead photographers whose style matches your vision. You'll receive the same quality, attention to detail, and editorial excellence—just with a different artist behind the camera.
Every gallery is still edited under my creative direction to ensure the Jeremy Glickstein Photography aesthetic remains consistent across all our 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
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.
Beyond the Wedding Day
The Same Cinematic Eye for Corporate Photography.
Team Headshots, Events, Branding & Food.
When we're not capturing one-of-a-kind weddings, we're behind the lens for Chicago's most prestigious companies — from intimate executive portraits to full-day team headshot sessions to black-tie galas for Fortune 500 clients. The same attention to comfort, the same cinematic quality, the same hand-edited finish. Just a different kind of milestone.
