Stylish Chicago wedding portrait of bride and groom in retro red leather booth showcasing cinematic editorial photography style
Romantic Chicago wedding photography session by Jeremy Glickstein Photography featuring couple in natural light
Chicago engagement photographer captures intimate moment as couple shares tender embrace during urban portrait session
Fine art Chicago wedding photography portrait showcasing cinematic lighting and editorial style
Fun Chicago engagement photos showing playful couple reaching for each other in front of colorful Chinatown mural

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.

As You Wish Check availability & schedule your free consultation
151 Five-Star Reviews
Preferred at Chicago's Finest Venues
Free Consultation

Here's what most couples don't find out until the sales call: Chicago wedding photography ranges from $4,950 to $11,000+. Jeremy-led collections start at $6,250 (Essential) — Signature at $7,450 is where most land. Associate-led starts at $4,950, same aesthetic, every frame edited by Jeremy. Two photographers. No batch filters. No outsourcing.

  • Jeremy-led: $6,250–$11,000+
  • Associate-led: $4,950–$7,750
  • Most couples invest: $6,250–$9,500
  • 151 five-star reviews · Preferred 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.
Every collection includes timeline coaching, curated gallery with print rights, and hand-edited images—never batch filters.

Jeremy-Led Collections

10+ years as actor, director & acting coach · Jeff Award winner · 151 five-star reviews

$6,250 – $11,000+

Intimate

Up to 5 Hours · Solo

$3,750

  • Solo photographer (Jeremy)
  • 400+ hand-edited images
  • 72-hour highlights
  • Full gallery in 3 weeks
  • Private online gallery

Done by dinner. Still extraordinary.

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Essential

Up to 8 Hours · Two Photographers

$6,250

  • Jeremy + second photographer
  • 500+ hand-edited images
  • 48-hour highlights
  • Full gallery in 5 weeks
  • Timeline planning + coordination

Single venue. Tight timeline. Nothing missed.

Reserve

Weekend

Up to 13 Hours · Rehearsal + Wedding

$9,500

  • Everything in Signature, plus:
  • Rehearsal dinner (up to 3 hrs)
  • 800+ hand-edited images
  • Full gallery in 4 weeks

The rehearsal toast deserves to be remembered too.

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Full Story

Up to 16 Hours · Complete Weekend

$11,000

  • Everything in Weekend, plus:
  • Day-after brunch (up to 2 hrs)
  • 1,000+ hand-edited images
  • 24-hour highlights
  • Full gallery in 3 weeks

Welcome drinks to farewell brunch. Every chapter.

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Associate-Led Collections

Unique artistic eye · Same cinematic aesthetic · Personally selected by Jeremy

✓ Every gallery 100% hand-edited by Jeremy

$4,950 – $7,750

Associate-Led

Intimate

Up to 5 Hours · Solo

$2,500

  • Solo photographer (Associate)
  • 400+ hand-edited images
  • 72-hour highlights
  • Full gallery in 3 weeks
  • All images edited by Jeremy

Elopement coverage. Same aesthetic.

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Associate-Led

Standard

Up to 9 Hours · Full Coverage

$4,950

  • Lead photographer (Associate)
  • 500+ hand-edited images
  • 48-hour highlights
  • Full gallery in 5 weeks
  • Timeline planning + coordination
  • All images edited by Jeremy

Full wedding day. Cinematic look — guaranteed.
Add second shooter: +$600

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Associate-Led

Full

Up to 10 Hours · Two Photographers

$5,750

  • Lead + second photographer
  • 600+ hand-edited images
  • 48-hour highlights
  • Full gallery in 5 weeks
  • Timeline planning + coordination
  • All images edited by Jeremy

Two photographers. Same standard. No compromise.

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Associate-Led

Weekend

Up to 13 Hours · Rehearsal + Wedding

$6,750

  • Everything in Full, plus:
  • Rehearsal dinner (up to 3 hrs)
  • 800+ hand-edited images
  • Full gallery in 4 weeks
  • All images edited by Jeremy

Extended coverage. Full weekend experience.

Secure Your Date
Associate-Led

Full Story

Up to 16 Hours · Complete Weekend

$7,750

  • Everything in Weekend, plus:
  • Day-after brunch (up to 2 hrs)
  • 1,000+ hand-edited images
  • 24-hour highlights
  • Full gallery in 3 weeks
  • All images edited by Jeremy

The complete story. Same obsessive edit.

Secure Your Date

What's actually different

  • Comfort-based direction. You'll forget the camera's there.
  • Creative collaboration. Bold vision? Themed concept? Let's build it.
  • Speed + craft. Highlights in 24–72 hours. Heirloom-ready edits.
  • Two photographers. Ceremony emotion + candid reaction. Same moment.
  • All lovers welcome. LGBTQ+ weddings celebrated, not just tolerated.
  • One editor. Jeremy. Every gallery. Whether he shot it or not.

151 ★★★★★ reviews · Preferred at Chicago Winery & Cuneo Mansion · Fearless Photographers · WPJA Featured · Zola Best of 2025

Configuration

Engagement Session — $725 Additional hour (two) — $750 Additional hour (solo) — $500 Additional 30 min (two) — $350 Additional 30 min (solo) — $250 Second photographer — $600 Third photographer — $300/hr Rush delivery — Let's discuss

How This Works

  1. Discovery Call. Your story. Your must-haves. What makes you nervous.
  2. Light-First Timeline. Built around golden hour, not arbitrary tradition.
  3. The Wedding. Calm when needed. Invisible when it counts.
  4. Preview & Delivery. Highlights in 24–72 hours. Full gallery + print shop.

Straight Answers

What do most couples invest?

$6,250–$9,500 for Jeremy-led with two photographers. Associate-led: $4,950–$7,750. All include timeline planning, highlights, full gallery.

Essential vs. Signature?

Essential ($6,250): 8 hours, two photographers. Signature ($7,450): 10 hours, engagement session included. Most couples land on Signature.

Jeremy-led vs. associate-led?

Jeremy-led: I'm your primary. Associate-led: One of my personally selected photographers. The constant: I edit every gallery myself.

When do we get photos?

Highlights: 24 hrs (Full Story), 48 hrs (most collections), 72 hrs (Intimate). Full gallery: 3–5 weeks.

We're awkward on camera.

Most of my couples are. 10+ years as actor, director, acting coach. You'll forget the camera's there.

LGBTQ+ weddings?

Love is love. Celebrated, not just tolerated.

Payment plans?

Yes. 50/50 or thirds. Final payment due one month before.

Can we customize?

Every collection is a starting point. Tell me your vision. Let's build.

Chicago Venues I Know Cold

300+ weddings across Chicago. I know which venues have the light, the backdrops, and the hidden corners that make photographers' jobs easy — and which ones require creative problem-solving. Not all venues photograph equally.

Indoor

  • Chicago Winery (preferred vendor) — Barrel rooms, industrial romance, warm candlelight
  • Lyric Opera of Chicago — Theatrical grandeur, dramatic architecture
  • The Rookery Building — Frank Lloyd Wright staircase, architectural history
  • Chicago Athletic Association — Rooftop views, Art Deco details
  • Artifact Events — Gallery minimalism, editorial canvas
  • The Walden — Bow-truss ceilings, floor-to-ceiling light
  • Gaelic Park — Crystal chandeliers, 50-acre grounds

Outdoor

  • North Avenue Beach — Skyline reflections, golden hour
  • Alfred Caldwell Lily Pool — Hidden gem, prairie serenity
  • Chicago Riverwalk — Urban energy, architectural backdrops
  • Promontory Point — Panoramic lake, dramatic skies
  • Garfield Park Conservatory — Victorian glass, lush greenery
  • Morton Arboretum — 1,700 acres of seasonal beauty

Why This Matters

Some venues make everyone look like they stepped out of a magazine. Others require knowing exactly where to stand at exactly what time. I help couples choose based on their vision — moody industrial, editorial polish, fairytale romance — not just what's trending on Pinterest.

For couples with creative vision: Industrial lofts, minimalist galleries, rooftops with skyline views — these are blank canvases. Perfect for elaborate themes, dramatic lighting, or ideas nobody's tried before. Tell me what you're imagining.

Haven't picked a venue yet? I'm happy to talk through options on our discovery call. Some venues photograph like a dream. Some need workarounds. Good to know ahead of time.

What Makes This Different

Most wedding photographers started as photographers. I came from theater — actor, director, acting coach. 10+ years learning how to help people feel comfortable under pressure, find emotional beats, build narrative arcs. Then I picked up a camera.

Direction That Doesn't Feel Like Direction

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."

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? An idea nobody's tried before? I live for that. Film noir speakeasy. Moody greenhouse editorial. Chinatown mural jumping shots.

Your imagination is the starting point. My job is execution.

Storytelling Over Shot Lists

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.

"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. 10/10 recommend."
— Jake & Alex

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? Let's talk.

From Inquiry to Album

No surprises. No hidden fees. Here's exactly what happens.

Before

Discovery call. 30 minutes. Your vision, your must-haves, what makes you nervous. If we're a fit, we move forward. If not, I'll refer you to someone better matched.

Contract + retainer. 50% holds your date. Balance due 30 days before. Credit cards, checks, Venmo/Zelle.

Pre-wedding planning. 4-6 weeks out: timeline optimization, shot list, engagement session scheduling (if included).

Wedding Day

I arrive early. Scout light. Stay calm when timelines shift — they always do.

My job: capture your story, keep things moving, get you back to cocktail hour as fast as possible.

After

24-72 hours: Highlights. 25-30 favorites while you're still buzzing. Social media, thank-you cards, reliving it fresh.

3-5 weeks: Full gallery. 500-1,000 hand-edited images depending on collection. Download, share, order prints. Every frame color-corrected and polished. No batch filters.

Optional

Albums + prints. Physical keepsakes through my online shop. Heirloom quality.

Straight Answers

300+ weddings. These come up every time.

"We're not photogenic."

Most people feel this way. I use movement-based direction instead of stiff posing. You'll forget the camera exists.

"Photogenic" is a myth. Real emotion makes great photos, not perfect jawlines.

"We're awkward but want creative photos."

That's not a contradiction — that's most of my favorite couples. Camera-shy AND wanting something cinematic? That's exactly what the theater background is for.

You can absolutely have both.

"We have a specific creative vision."

Good. Themed concepts, elaborate setups, ideas nobody's tried — that's the fun part. Film noir speakeasy. Moody greenhouse editorial. Vintage Hollywood.

My job is execution, not just documentation.

"What about rain / dark venues / difficult families?"

Rain: Some of my favorite photos. Moody skies, dramatic light, reflections. Cinematic gold.

Dark venues: I specialize in low-light. Fast lenses, subtle off-camera lighting. Your guests won't notice I'm working.

Difficult families: Divorced parents, opinionated aunts, kids who'd rather eat cake. I've wrangled them all. Calm, patient, discreet.

"What if you're sick on our wedding day?"

Network of trusted backup photographers — vetted, insured, capable. In 8+ years, I've never missed a wedding. But if the unthinkable happens, you're covered.

"Can we see the RAW files?"

No. RAW files are unfinished sketches — 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?

Drop us a line to discuss your custom collection, below!