Investment & Pricing | Jeremy Glickstein Photography | Chicago Wedding Photographer
Romantic Chicago wedding photography featuring couple in soft natural light
151 Five-Star Reviews Preferred Vendor — Chicago Winery & Cuneo Mansion
Former Actor, Director & Acting Coach (Steppenwolf credit) Jeff Award Winner

Chicago Wedding Photographer

Your Heirloom Awaits

If you're reading this, you care about the details as much as I do.

Cinematic. Painterly. Hand-edited by me — never AI, never outsourced.

10+ years in theater. Jeff Award winner. Steppenwolf Theatre Company. A decade of fine art street photography before ever touching a wedding.

You'll feel comfortable. Your photos will be art. That's the whole point →

Build Your Collection

No templates. No preset bundles. You configure the coverage, team, and deliverables.

Every Collection

18 weddings. That's it. Peak season books 12–18 months out. If I'm unavailable, I'll match you with the right associate.

Why Couples Choose Us

Half want stunning images but feel awkward being photographed. Half are bold creatives who need the right collaborator. Both get what they came for.

Theater-Trained

10+ years at Steppenwolf taught me how to help people relax. No stiff poses. No "say cheese." Just you.

Fast Highlights

24–72 hours. Share the best moments before you've written a single thank-you card.

Hand-Edited. Always.

You hire me, you get me. Every image. Never AI. Never outsourced. That's how the cinematic look stays consistent.

All Love Celebrated

LGBTQ+. Non-traditional. Elopements. Second marriages. Every love story, told beautifully.

"From the first meeting, we felt supported by his professionalism, intentionality, and easy-to-talk-to personality. He remained focused on what we wanted while incorporating his own incredible artistic visions throughout the day — without making it feel like a photoshoot. We were so happy that we had the opportunity to work with Jeremy."

— Verified Wedding Client, Trustpilot

Wedding Collections

Cinematic storytelling. Documentary heart. Your day — authentically captured.

Most couples configure between $6,250–$9,500 for Jeremy-led. Associate-led starts at $4,950.

Jeremy-Led Collections

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

$3,750 – $11,000+

Intimate

$3,750

Up to 5 Hours · Solo

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

Simple. Beautiful. Done by dinner.

Secure Your Date

Essential

$6,250

Up to 8 Hours · Two Photographers

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

Single-venue city weddings. Shorter timelines. Complete coverage.

Reserve

Signature

$7,450

Up to 10 Hours · Two Photographers

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

The full story — getting ready to grand exit. No clock-watching.

Reserve

Weekend

$9,500

Up to 13 Hours · Rehearsal + Wedding

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

The rehearsal dinner toast deserves to be remembered too.

Inquire

Full Story

$11,000

Up to 16 Hours · The Complete Weekend

  • 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.

Inquire

Associate-Led Collections

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

✓ Every gallery 100% hand-edited by Jeremy

$2,500 – $7,750

Associate-Led

Intimate

$2,500

Up to 5 Hours · Solo

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

Beautiful elopement coverage. Same aesthetic.

Secure Your Date
Associate-Led

Standard

$4,950

Full Coverage · Up to 9 Hours

  • Lead photographer (Associate)
  • 500+ hand-edited images
  • 48-hour highlights
  • Full gallery within 5 weeks
  • Timeline planning + vendor coordination
  • All images edited by Jeremy
Add second shooter: +$600 for dual coverage all day.

Full wedding day coverage at an accessible investment. Perfect for couples who prioritize quality over hours.

Secure Your Date
Associate-Led

Full

$5,750

Complete Wedding · Up to 10 Hours

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

Full coverage with two photographers. Same cinematic look — guaranteed.

Secure Your Date
Associate-Led

Weekend

$6,750

Wedding + Rehearsal · Up to 13 Hours

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

Extended coverage for the full wedding weekend experience.

Secure Your Date
Associate-Led

Full Story

$7,750

The Complete Weekend · Up to 16 Hours

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

The complete story at an accessible investment.

Secure Your Date

Don't see exactly what you need? Every wedding is different. Tell me your plan and I'll tailor coverage, team size, and deliverables to fit. Popular venue? Check out my venue guides or let's talk.

Proposal Photography

Discreet coverage, perfect timing, iconic Chicago backdrops.

I position myself before you arrive — invisible until after the "yes." Then we celebrate with portraits at your chosen location. Highlights delivered within 48–72 hours so you can share the news immediately. See how I capture proposals →

Essentials

$72520 min
  • Discreet timing + exact positioning
  • The moment + quick portraits
  • 48–72 hour highlights

Simple proposals at one iconic spot

Secure Your Date

Signature

$8251.25 hrs
  • Location consult + timing-by-light
  • The moment + mini portrait loop
  • 48–72 hour highlights

Proposals with multiple portrait locations

Reserve

Cityscape

$9251.75 hrs
  • Rooftop/skyline vantage optimization
  • Multiple portrait spots
  • 48–72 hour highlights

Skyline-focused with scenic variety

Reserve

Private Venue

$9852.5 hrs
  • Private venue or styled setup
  • Family/friends reveal options
  • 48–72 hour highlights

Restaurant proposals with family celebration

Inquire

"Proposing can be a stressful thing and Jeremy helped me with nailing down the best location and time. He communicated throughout the entire process, up to a few minutes before letting me know he was ready. I can't even start to talk through how good the pictures came out. I gave him a vision and he made it come to life better than I could've expected."

— Verified Google Review · Read more reviews →

Engagement Sessions

Cinematic, creative portraits with natural direction — frame-worthy and real.

This is where most camera-shy couples realize: "Oh, this isn't going to be awkward." You'll forget the camera's there. We enter the wedding day not as strangers, but as co-conspirators. Professional editing, painterly light, sublime results. See sessions →

Local

$7251 hr
  • 1 location
  • Wardrobe guidance
  • Private gallery
Inquire

Signature

$8251.5 hrs
  • 1–2 locations
  • Golden hour timing
  • 60–120 edited images
Reserve

City Loop

$9252 hrs
  • Neighborhood + skyline combo
  • 2 outfits
  • Private gallery
Reserve

Cinematic

$9852.5 hrs
  • Styled concept + 2–3 locations
  • Director-led movement & micro-prompts
  • Optional rush preview
Inquire

"We had a great time getting creative and capturing our relationship through his photography. Jeremy is a person who is passionate about his craft, and when he does his work he is very proactive and enthusiastic about it. We couldn't be happier with the results."

— Kassy and Tyler, Engagement Session · View portfolio →

Configuration

  • Engagement Session — $725 standalone (included with Signature+)
  • Additional hour (two photographers) — $750
  • Additional hour (solo) — $500
  • Additional 30 min (two photographers) — $350
  • Additional 30 min (solo) — $250
  • Second photographer (Intimate/Standard) — $600
  • Third photographer — $300/hr
  • Rush deliveryLet's discuss

Common Questions

"We feel awkward in photos. Will this be uncomfortable?"

Half my couples say this. I don't point a camera at you and say "smile." I spent 10+ years in theater learning how to help people relax. I give you something real to do — tell each other a story, whisper something funny. You'll be focused on each other. You'll forget I'm there. That's when it works. More on my approach →

"What's the difference between Essential and Signature?"

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

"Why are you more expensive than some photographers?"

I edit every image myself. No AI, no overseas editing. I limit my calendar to 18 weddings so I can give each couple full attention — planning through delivery. That's a different experience.

"What's the difference between Jeremy-led and associate-led?"

Jeremy-led: I'm your primary photographer. Associate-led: One of my personally selected photographers — each brings their own unique flair while matching the aesthetic you want. Light and airy, dark and moody, editorial, Super 8-esque — I have the talent. The constant: I edit every gallery myself. That's how the look stays consistent. Meet the team →

"What's your background?"

10+ years in professional theater — Steppenwolf Theatre Company, Jeff Award winner, IMDb credits. A decade of fine art street photography. That background taught me how to help people reveal their authentic selves on camera. Full story →

"When do we get our photos?"

Highlights: 24 hours (Full Story), 48 hours (Signature/Essential/Weekend), 72 hours (Intimate).
Full gallery: 3–5 weeks. You'll get a specific date at booking.

"Do you shoot LGBTQ+ weddings?"

Yes. Love is love. Your story matters. I'd be honored to tell it.

"What if our venue isn't 'Instagram-worthy'?"

I started as a street photographer. I can make a parking lot cinematic. Light, emotion, framing — that's what makes photos. Bring me your community center, your backyard, your favorite dive bar. See examples →

"Do you offer payment plans?"

Yes. 50/50 split (half now, half one month before) or thirds. Final payment always due one month before the wedding.

"What happens if something goes wrong?"

Professional liability insurance. Backup equipment at every shoot. Relationships with top Chicago venues. 300+ weddings, zero missed moments.

"Can we customize a collection?"

Every collection is a starting point. Tell me your vision and I'll configure coverage, team, and deliverables to fit. Let's build.

Limited Availability — Endless Possibility

18 weddings. Peak season books 12–18 months out. Let's see if we're right for each other.

Jeff Award Winner · Former Steppenwolf Theatre
151 Five-Star Reviews · Preferred: Chicago Winery & Cuneo Mansion