Chicago + Destination Wedding & Engagement Photography
Just be yourselves—we'll make photos that look and feel like a dream.
Whether you feel awkward in front of the camera or have a bold creative vision—I'm here. Cinematic, painterly, true.
Chicago wedding photography packages range from $2,750 to $11,000+. Jeremy Glickstein-led collections start at $7,000 for full-day coverage, with associate-led collections from $5,500. Intimate half-day coverage starts at $2,750 (associate) or $3,750 (Jeremy). Most couples invest $7,000–$9,500 for complete coverage with two photographers.
- Jeremy-led collections: $7,000–$11,000+
- Associate-led collections: $5,500–$7,750
- Intimate half-day: $2,750–$3,750
- Most couples invest: $7,000–$9,500
- 151+ five-star reviews · Preferred vendor at Chicago Winery & Cuneo Mansion
Wedding Photography Collections
For couples who want to feel comfortable and get something extraordinary.
Photojournalism meets fine art meets cinematic portraiture—story first, always.
Every collection includes timeline coaching, curated online gallery with print rights, and hand-finished edits—never batch filters.
Jeremy-Led Collections
10+ years as actor, director & acting coach · Jeff Award winner · 151+ five-star reviews
$7,000 – $11,000+
Full Day
Complete Wedding · Up to 10 Hours
From $7,000
- Jeremy + second photographer
- 600+ hand-edited images
- 48-hour highlights
- Full gallery within 5 weeks
- Complimentary engagement session
- Timeline planning + vendor coordination
The full story — getting ready to grand exit. No clock-watching.
Lock In Your DateWeekend
Wedding + Rehearsal · Up to 13 Hours
From $9,500
- Everything in Full Day, plus:
- Rehearsal dinner coverage (2nd photographer, up to 3 hrs)
- 800+ hand-edited images
- 48-hour highlights
- Full gallery within 4 weeks
Because the rehearsal dinner toast deserves to be remembered too.
Request ProposalFull Story
The Complete Weekend · Up to 16 Hours
From $11,000
- Everything in Weekend, plus:
- Day-after brunch coverage (2nd photographer, up to 2 hrs)
- 1,000+ hand-edited images
- 24-hour highlights
- Full gallery within 3 weeks
Everything. Fast. For couples who want it all and don't want to wait.
Build My CollectionAssociate-Led Collections
Same artistic direction · Same hand-edited quality · Personally selected & trained by Jeremy
$5,500 – $7,750
Full Day
Complete Wedding · Up to 10 Hours
From $5,500
- Lead + second photographer
- 600+ hand-edited images
- 48-hour highlights
- Full gallery within 5 weeks
- Timeline planning + vendor coordination
- All images edited by Jeremy for brand consistency
Full coverage, exceptional quality, accessible investment.
Check AvailabilityWeekend
Wedding + Rehearsal · Up to 13 Hours
From $6,750
- Everything in Full Day, plus:
- Rehearsal dinner coverage (2nd photographer, up to 3 hrs)
- 800+ hand-edited images
- 48-hour highlights
- Full gallery within 4 weeks
- All images edited by Jeremy for brand consistency
Extended coverage for the full wedding weekend experience.
Check AvailabilityFull Story
The Complete Weekend · Up to 16 Hours
From $7,750
- Everything in Weekend, plus:
- Day-after brunch coverage (2nd photographer, up to 2 hrs)
- 1,000+ hand-edited images
- 24-hour highlights
- Full gallery within 3 weeks
- All images edited by Jeremy for brand consistency
The complete story at an accessible investment.
Check AvailabilityIntimate Collections
Elopements, micro-weddings & courthouse ceremonies
Intimate
Half Day · Up to 5 Hours
From $3,750
- Solo photographer (Jeremy)
- 400+ hand-edited images
- 72-hour highlights
- Full gallery within 3 weeks
- Private online gallery
For the couple who wants it simple, beautiful, and done by dinner.
Single venue, 60 guests or fewer
Intimate
Half Day · Up to 5 Hours
From $2,750
- Solo photographer (Associate)
- 400+ hand-edited images
- 72-hour highlights
- Full gallery within 3 weeks
- All images edited by Jeremy for brand consistency
Beautiful elopement coverage at an accessible investment.
Single venue, 60 guests or fewer
Why couples choose cinematic coverage
- Comfort-based direction: Natural prompts that don't feel forced. You'll forget the camera's there.
- Creative collaboration welcome: Have a bold vision? Themed concepts? "What if we did something completely different" ideas? Let's design it together.
- Speed + craft: Highlights in 24–72 hours; heirloom-ready edits that aren't batch-filtered.
- Two photographers: Ceremony emotion + candid reaction, same moment. Nothing missed.
- All lovers welcome: LGBTQ+ allies. Non-traditional ceremonies celebrated. Camera-shy couples? That's my specialty.
- Consistent quality: Jeremy personally edits every gallery—whether he shot it or an associate did.
151+ ★★★★★ reviews · Preferred vendor at Chicago Winery & Cuneo Mansion · Fearless Photographers · WPJA Featured · Zola Best of 2025
Add-Ons
Need more time, another photographer, or faster delivery? Custom add-ons available.
Your Day, Our Process
- Discovery Call: Your story, must-haves, and thresholds for adventure.
- Light-First Timeline: Space for spontaneity so unscripted magic can unfold.
- The Wedding: Calm direction when needed; quiet observation when it counts.
- Preview & Delivery: 24–72 hour highlights; full gallery + print-shop convenience.
Wedding Photography — Quick Answers
What do most couples invest?
$7,000–$9,500 for complete Jeremy-led coverage with two photographers. Associate-led collections range from $5,500–$7,750. All include timeline planning, highlights, and full gallery delivery.
What's the difference between Jeremy-led and associate-led?
Jeremy-led means Jeremy is your primary photographer. Associate-led features one of Jeremy's personally trained photographers—same artistic direction, same editing style (Jeremy edits every gallery), more accessible investment.
When do we get photos?
Highlights: 24 hrs (Full Story), 48 hrs (Full Day & Weekend), 72 hrs (Intimate). Full gallery: 3–5 weeks depending on collection.
Weekend vs. Full Story?
Both include rehearsal dinner. Full Story adds day-after brunch, 24-hour highlights (vs. 48), and faster full gallery (3 weeks vs. 4).
What if we're awkward on camera?
Most of my couples are. I spent 10+ years as an actor, director, and acting coach—I use natural prompts that don't feel forced. You'll forget the camera's there.
Travel for destinations?
Yes—Chicago, the Midwest, and select destinations worldwide. Travel fees vary by location.
LGBTQ+ weddings?
Love is love. Non-traditional ceremonies and same-sex weddings aren't just welcome—they're celebrated.
Payment plans?
Yes. Reserve with a retainer, then split the balance into 2–3 payments on a schedule that works for you.
Preferred Venues & Chicago Wedding Locations
I've photographed 100+ weddings across Chicago and know which venues offer the best light, the most dramatic backdrops, and where to find hidden photo-worthy corners. Not all venues photograph equally—and that matters when you're investing $6,500+ in coverage.
Indoor Favorites
- Chicago Winery (preferred vendor) — Barrel rooms, industrial romance, warm candlelight
- Lyric Opera of Chicago — Theatrical grandeur, dramatic architecture, world-class elegance
- The Rookery Building — Frank Lloyd Wright staircase, architectural history
- Chicago Athletic Association Hotel — Rooftop views, Art Deco details
- Artifact Events — Gallery-style minimalism, editorial canvas
- The Walden — Bow-truss ceilings, whitewashed brick, rooftop skyline romance
- Gaelic Park — Crystal chandeliers, waterfall pergola, authentic Irish grandeur
Outdoor / Natural Environment Favorites
- North Avenue Beach — Skyline reflections, golden hour magic
- Lincoln Park (Alfred Caldwell Lily Pool) — Hidden gem, prairie-style serenity
- Chicago Riverwalk — Urban energy, architectural backdrops
- Promontory Point — Panoramic lake views, dramatic skies
- Garfield Park Conservatory — Lush greenery, Victorian glass architecture
- Morton Arboretum — 1,700 acres of seasonal beauty
Why Venue Matters More Than You Think
Some venues have killer natural light that makes everyone look like they stepped out of a magazine (The Walden's floor-to-ceiling windows, I'm looking at you). Others offer architectural drama that turns every portrait into a cinematic frame (hello, Lyric Opera).
I help couples choose based on their vision—not just Yelp reviews or "what everyone else is doing." Want moody, painterly light? We're talking industrial lofts with bow-truss ceilings. Want editorial polish? Think minimalist galleries or Art Deco ballrooms. Want classic elegance? Gaelic Park's crystal chandeliers and 50-acre grounds deliver fairytale romance.
For couples with creative vision: Some venues are blank canvases—industrial lofts, minimalist galleries, rooftops with skyline views. Perfect for elaborate themes, dramatic lighting setups, or "let's do something nobody's done here before." Tell me what you're imagining and I'll tell you which spaces can make it happen.
Pro tip: If you haven't picked a venue yet, I'm happy to chat through options during our discovery call. I know which venues photograph like a dream—and which require creative problem-solving (totally doable, just good to know ahead of time).
What Makes This Different
Most wedding photographers started as... photographers. I came from theater—Chicago actor, director, acting coach. I know how to help you feel comfortable without it feeling like direction. How to read a room. When to step in, when to disappear.
🎬 Theater Training Meets Wedding Day
What I learned on stage: How to make people comfortable under pressure. How to find emotional beats in a scene. How to create a narrative arc—not just capture random moments.
What this means for you: Your wedding photos won't feel like a checklist. They'll feel like scenes from a film you'd want to watch again and again. There's a why behind every frame.
🎭 Direction That Feels Natural
I don't say "stand here, smile at the camera." I say "walk toward me like you're late for dinner" or "whisper something that'll make them laugh."
The result? You forget the camera exists. Your partner forgets the camera exists. We get real emotion—not performed smiles.
🎨 Creative Collaboration
Have a vision? A theme? A "what if we did this crazy thing" idea? I live for that. My fine art background means I can help you execute ambitious concepts—not just capture them.
Recent examples: Film noir speakeasy vibes. Moody greenhouse editorial. Chinatown mural jumping shots. Your imagination is the starting point.
📖 Storytelling Over Shot Lists
Sure, I'll capture your family formals (fast and flattering). But what I'm really watching for? The moment your dad tears up during the toast. The way your partner looks at you when they think no one's watching. The quiet pause before you walk down the aisle.
Those are the keepers. The shots that make you cry 20 years later.
"Jeremy is such an amazing photographer! My husband and I had a couples photoshoot with him last autumn. I'm one of those people who get super nervous having photos taken of me and Jeremy helped me feel natural and comfortable throughout the photoshoot. The photos turned out beautiful and we are just so happy that we decided to go with Jeremy as a photographer. 10/10 recommend!"—Jake & Alex
Bottom line: If you want a photographer who shows up, clicks the shutter 1,000 times, and disappears—I'm not your guy. But if you want someone who helps you feel comfortable and brings creative vision to your day? Let's talk.
What to Expect: From Inquiry to Album
Here's exactly what happens after you fill out the contact form. No surprises, no hidden fees, no "we'll figure it out later."
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1
Discovery Call (30 minutes)
We talk vision, logistics, and whether we're a good fit. I'll ask about your style, your must-haves, and what you're nervous about (if anything). No pressure, just conversation. If it feels right, we move forward. If not, I'll refer you to someone who's a better match.
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2
Contract + Retainer
I send over a contract and invoice. 50% retainer holds your date. Balance due 30 days before the wedding. I accept credit cards, checks, and Venmo/Zelle.
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3
Pre-Wedding Planning
About 4-6 weeks before the wedding, we hop on another call to review:
- Timeline: I help optimize for light (golden hour portraits are *chef's kiss*)
- Shot list: Family formals, must-have moments, anything you're worried about missing
- Engagement session: If included in your package, we schedule this 3-6 months before the wedding
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4
Wedding Day
I arrive early, scout light, and stay calm even when timelines shift (they always do). My job: capture your story, keep things moving, and make sure you don't miss cocktail hour. You're back with guests in 15 minutes post-ceremony.
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5
Preview (48-72 hours)
You get 25-30 favorites while you're still buzzing from the day. Perfect for social media, thank-you cards, or just reliving the magic while it's fresh.
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6
Full Gallery (4-6 weeks)
800-1,000 hand-edited images in a private online gallery. Download, share, order prints—your call. Every image is color-corrected, exposure-adjusted, and polished. No batch filters. No "meh, that'll do." Just heirloom-ready work.
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7
Album Design (optional)
Want a physical keepsake? My online shop offers a multitude of products that can feature your images, including albums.
Ready to get started?
Check My AvailabilityCommon Concerns (And How We Handle Them)
I've shot 300+ weddings. These are the questions I hear most—and the honest answers.
"We're not photogenic."
Most people feel this way. That's why I use movement-based direction instead of stiff posing. You'll forget the camera exists within 10 minutes. I promise.
Also: "Photogenic" is a myth. What makes a great photo is real emotion, not a perfect jawline. I'll make you look like yourselves—just the most radiant, in-love version.
"We have a really specific creative vision."
Good. I want to hear every detail. Themed concepts, elaborate setups, "what if we..." ideas—that's not extra work, that's the fun part.
My fine art and theater background means I can help you execute ambitious ideas, not just document them. Film noir vibes? Moody greenhouse editorial? Vintage Hollywood? Let's build it together.
"We're awkward but also want creative photos."
That's not a contradiction—that's most of my favorite couples. You can be introverts who are also massive Star Wars fans. Camera-shy AND wanting something cinematic.
My theater background helps you feel comfortable enough to forget the camera exists, AND my fine art eye ensures the images are gallery-worthy. You can absolutely have both.
"We don't want to miss cocktail hour."
Me neither. That's why we do 80% of portraits before the ceremony (first look recommended but not required). Post-ceremony? We knock out family formals efficiently. You're back with guests before they finish their first drink.
That said, couple's portraits are one of the main draws for our clients—and they understand this takes time. We don't rush, especially portraits. If the original timeline was 8.5 hours but it needs to be 9 or 9.5, we'll tell you. You have one shot to do this right.
"What if it rains?"
I've shot 300+ weddings. Rain happens. I bring umbrellas, scout covered backup spots, and honestly? Some of my favorite photos are from rainy days. Moody skies, dramatic light, reflections in puddles—it's cinematic gold.
"Our venue is really dark."
I specialize in low-light photography. Clean, flattering images without killing the ambiance with harsh flash. I use fast lenses, high-end gear, and subtle off-camera lighting when needed. Your guests won't even notice I'm working.
"What if you're sick on our wedding day?"
I have a network of trusted backup photographers (all vetted, all insured, all capable of rocking your wedding day). In 8+ years, I've never missed a wedding. But if the unthinkable happens, you're covered. No exceptions.
"How do we know our photos won't look dated in 10 years?"
I shoot for timeless fine art over trendy. No Instagram filters, no heavy vignettes, no "orange and teal" color grading. Unique, dreamy & timeless.
"What if our families are... difficult?"
I've wrangled every family dynamic imaginable. Divorced parents who don't speak. Opinionated aunts. Kids who'd rather play with the cake than pose for portraits. I'm calm, patient, and discreet. Your photos will show love, not drama.
"Can we see the RAW files?"
Short answer: No. Long answer: RAW files are like unfinished sketches. They're not color-corrected, not cropped, not polished. What you receive is the finished work—the version I'd put in a museum. Would you ask a chef for the raw ingredients after dinner?
Still have questions?
Let's Talk