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 →

Investment Overview

Every wedding is custom. Pricing depends on your date, venue, and coverage needs.

  • Weddings

    $5,000 – $9,500+

    Most couples invest $5,500–$7,000. Custom proposals based on your venue, date, and vision.

    Learn More

  • Proposals

    $725 – $985

    Discreet. Perfectly timed. The moment, captured impeccably. Learn more →

    Plan Your Proposal

  • Engagements

    $725 – $985

    Cinematic portraits. Natural direction. Frame-worthy and real. View sessions →

    View Sessions

Every Collection

18 weddings. That's it. Peak season books 12–18 months out.

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 Photography

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

Wedding Collections

$5,000 – $9,500+

Most couples invest $5,500–$7,000

"Every wedding is custom — pricing depends on your date, venue, and coverage needs. Let's talk about yours."

What Shapes Your Investment

Four factors determine your custom proposal

Coverage Hours

5 hours for intimate celebrations to 16+ hours for full weekends

💍

Engagement Session

Included with most collections — or add separately

Delivery Speed

24-hour highlights to 72-hour turnaround options

📷

Team Size

Solo coverage or two photographers for complete storytelling

What's Included

Every collection starts with these essentials

Hand-Edited by Me

Every image, every gallery. Never AI. Never outsourced. That's how the look stays consistent.

Theater-Trained Direction

No stiff poses. No "say cheese." I give you something real to do — you'll forget I'm there.

Timeline Strategy

I work with your planner and venue to optimize lighting and flow. You stay present.

Private Gallery

High-resolution images with full print rights. Download, share, print — forever.

Fast Highlights

24–72 hours depending on collection. Share the best moments while they're still fresh.

Backup Everything

Dual card slots. Backup equipment at every shoot. 300+ weddings, zero missed moments.

What's Different

This isn't a commodity. Here's why.

Steppenwolf Training

10+ years as actor, director, and acting coach. I know how to help people reveal their authentic selves.

Fine Art Foundation

A decade of street photography before weddings. Light, composition, and timing are instinct.

Limited Calendar

18 weddings per year. Full attention from inquiry to final delivery. No assembly line.

Venue Relationships

Preferred vendor at Chicago's finest venues. Coordinators trust me. That means better access, smoother days.

Configure Your Collection

Popular additions and customizations

  • Engagement session — included with most collections
  • Additional coverage hours — extended or multi-day events
  • Second photographer — complete storytelling, multiple angles
  • Rehearsal dinner — capture the toasts and gathering
  • Day-after brunch — the farewell chapter
  • Rush delivery — priority turnaround available

How It Works

1

Connect

Tell me about your wedding — date, venue, vibe. I'll confirm availability.

2

Custom Proposal

You'll receive a tailored proposal based on your specific needs — not a one-size-fits-all package.

3

Secure Your Date

Sign and pay retainer. Your date is locked. We start planning.

4

Wedding Day

You'll feel comfortable. I'll capture it all. Highlights delivered fast.

Ready to talk specifics? Every conversation starts with your vision. Let's build your collection →

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 →

Additional Options

  • Engagement Session — $725 standalone (included with most wedding collections)
  • Additional hour (two photographers) — $750
  • Additional hour (solo) — $500
  • Second photographer — $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 →

"How do you determine pricing for weddings?"

Every wedding is different. Your investment depends on coverage hours, team size, engagement session inclusion, and delivery timeline. Most couples invest $5,500–$7,000. After we talk about your specific day, I'll send a custom proposal tailored to your needs — not a one-size-fits-all package.

"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 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: 24–72 hours depending on collection.
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?"

That's the entire point. Tell me your vision and I'll configure coverage, team, and deliverables to fit. Let's build.

"You Complete Me."

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