Investment & Pricing | Jeremy Glickstein Photography | Chicago Wedding Photographer
Iconic Rookery Building spiral staircase wedding portrait with bride descending marble stairs in Chicago
Jeff Award Winner Former Steppenwolf Theater Actor 151 Five-Star Reviews Preferred Vendor — Chicago Winery & Cuneo Mansion

Your Heirloom Awaits

Cinematic. Painterly. Hand-edited by me.

10+ years in theater & film — Jeff Award winner, Steppenwolf Theatre Company — plus a decade as a fine art street photographer.
What does that mean for you?

You'll feel comfortable. Your photos will be art.

Investment Overview

Every couple is different. Here's where most couples land — but let's talk about what makes sense for your day.

  • Weddings

    From $2,500 – $11,000+

    Half-day elopements to full weekend coverage. Jeremy-led collections from $7,000, associate-led from $5,500. Most couples invest $7,000–$9,500.

    See Wedding Collections

  • Proposals

    $750 – $1,100

    Discreet, timed-to-the-minute coverage. I position myself before you arrive — invisible until after the "yes."

    Plan Your Proposal

  • Engagements

    $750 – $1,050

    Cinematic portraits with natural direction. You'll forget the camera's there.

    See Engagement Sessions

Every Collection Includes

  • Comfort-based direction (no awkward posing)
  • Hand-edited by me — never AI, never outsourced
  • Timeline coaching + lighting strategy
  • Private online gallery with print rights
  • Camera-shy friendly approach

I photograph 20–25 weddings per year to give every couple my full attention. Peak season dates book 12–18 months in advance.

Why Camera-Shy Couples Choose Us

About 70% of my couples tell me upfront: "We hate having our photos taken." Sound familiar? You're in good company.

Theater-Trained Comfort

10+ years at Steppenwolf taught me how to help people relax and reveal their authentic selves. No stiff poses. No awkward "say cheese." Just you, being you.

24–72 Hour Highlights

Share the best moments before you've even opened your thank-you cards. Same-night teasers available for premium collections.

Hand-Edited. Always.

You hire me, you get me. Every image touched by my hands — never AI, never outsourced overseas. That's how I maintain the cinematic, painterly look.

All Love Celebrated

LGBTQ+ weddings, non-traditional ceremonies, elopements, second marriages — every love story deserves to be 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 meets photojournalism. Your day, your way — captured authentically.

What most couples invest: $7,000–$9,500 for complete Jeremy-led coverage with two photographers, timeline planning, and highlights within 24–72 hours. Associate-led collections from $5,500.

Jeremy-Led Collections

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

$7,000 – $11,000+

Most Popular

Full Day

$7,000

Complete Wedding · Up to 10 Hours

  • 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. This is what 80% of couples choose.

Lock In Your Date

Weekend

$9,500

Wedding + Rehearsal · Up to 13 Hours

  • Everything in Full Day, plus:
  • Rehearsal dinner coverage (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 Proposal
Complete Experience

Full Story

$11,000

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 — fastest delivery
  • Full gallery within 3 weeks

The complete story — every moment from welcome drinks to farewell brunch — delivered faster than any other collection.

Build My Collection

Associate-Led Collections

Same artistic direction · Same cinematic aesthetic · Personally selected & trained by Jeremy

✓ Every gallery 100% hand-edited by Jeremy

$5,500 – $7,750

Associate-Led

Full Day

$5,500

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, exceptional quality, accessible investment. Same cinematic look — guaranteed.

Check Availability
Associate-Led

Weekend

$6,750

Wedding + Rehearsal · Up to 13 Hours

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

Extended coverage for the full wedding weekend experience.

Check Availability
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.

Check Availability

Intimate Collections

Elopements, micro-weddings & courthouse ceremonies

Jeremy-Led

Intimate

$3,750

Half Day · Up to 5 Hours

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

For couples who want it simple, beautiful, and done by dinner.
Single venue, 60 guests or fewer

Check Availability
Associate-Led

Intimate

$2,500

Half Day · Up to 5 Hours

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

Beautiful elopement coverage at an accessible investment.
Single venue, 60 guests or fewer

Check Availability

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. 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.

Essentials

$75020 min
  • Discreet timing + exact positioning
  • The moment + quick portraits
  • 48–72 hour highlights

Simple proposals at one iconic spot

Check Availability
Most Popular

Signature

$8501.25 hrs
  • Location consult + timing-by-light
  • The moment + mini portrait loop
  • 48–72 hour highlights

Proposals with multiple portrait locations

Plan My Proposal

Cityscape

$9501.75 hrs
  • Rooftop/skyline vantage optimization
  • Multiple portrait spots
  • 48–72 hour highlights

Skyline-focused with scenic variety

Reserve

Private Venue

$1,1002.5 hrs
  • Private venue or styled setup
  • Family/friends reveal options
  • 48–72 hour highlights

Restaurant proposals with family celebration

Start Planning

"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

Getting married after? Book your wedding within 60 days of your proposal and receive a $500 credit toward any wedding collection.

Engagement Sessions

Cinematic 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. True color editing, painterly light, zero cheese.

Local

$7501 hr
  • 1 location
  • Wardrobe guidance
  • Private gallery
Book
Most Popular

Signature

$8501.5 hrs
  • 1–2 locations
  • Golden hour timing
  • 60–120 edited images
Lock In Your Date

City Loop

$9502 hrs
  • Neighborhood + skyline combo
  • 2 outfits
  • Private gallery
Reserve

Cinematic

$1,0502.5 hrs
  • Styled concept + 2–3 locations
  • Director-led movement & micro-prompts
  • Optional rush preview
Start Planning

"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

Add-Ons & Customization

Need more time, another photographer, or faster delivery? Let's make it work.

  • Engagement Session — $750 standalone (included with Full Day+)
  • Extra hour (two photographers) — $750
  • Extra hour (one photographer) — $500
  • Extra 30 min (two photographers) — $350
  • Extra 30 min (one photographer) — $250
  • Second photographer for Intimate — $600 (5 hrs)
  • Third photographer — $300/hr
  • Rush delivery — Let's talk, depends on your timeline

Questions You Might Be Thinking

"We hate having our photos taken. Will this be awkward?"

About 70% of my couples say this. Here's the thing: I don't just point a camera at you and say "smile." I spent 10+ years in theater learning how to help people feel comfortable. I'll give you something real to do — tell each other a story, whisper something that makes you laugh. You'll be so focused on each other, you'll forget I'm there. That's when the magic happens.

"Why are you more expensive than some photographers?"

Two reasons: First, I edit every single image myself. No AI, no overseas editing farms. You hire me, you get me. Second, I limit my calendar to 20–25 weddings per year so I can give every couple my full attention — not just on your wedding day, but in planning, timeline coaching, and delivery. That's a different experience than volume photographers who shoot 50+ weddings and outsource everything.

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

Jeremy-led means I'm your primary photographer. Associate-led features one of my personally trained photographers — same artistic direction, same editing style. Here's what doesn't change: I edit every gallery myself, regardless of who shot it. That's how I guarantee the same cinematic, painterly look across all collections.

"What's your background?"

Before photography, I spent 10+ years in professional theater — including work at Steppenwolf Theatre Company, one of America's most respected theaters. I won a Jeff Award (theater's equivalent of a Tony) and have credits on IMDb. That background taught me how to help people reveal their authentic selves on camera. It's why camera-shy couples consistently say my sessions feel different.

"When do we get our photos?"

Highlights: 24 hours (Full Story), 48 hours (Full Day & Weekend), or 72 hours (Intimate).
Full gallery: 3–5 weeks depending on collection. I'll give you a specific date when you book.

"Do you shoot LGBTQ+ weddings?"

Absolutely. Love is love. Non-traditional ceremonies and same-sex weddings aren't just welcome — they're celebrated. Your love story matters, and 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 look cinematic. Your venue matters way less than you think. Light, emotion, and framing — that's what makes photos beautiful. Bring me your community center, your backyard, your favorite dive bar. I'll make it look like a movie.

"Do you offer payment plans?"

Yes. Two options: 50% to reserve your date, 50% due one month before your wedding. Or split it into three equal payments — a third immediately, a third at the midway point, and a third one month before. Either way, your final payment is due one month before the wedding.

"What happens if something goes wrong?"

I carry professional liability insurance, bring backup equipment to every shoot, and have relationships with top Chicago venues who trust me to handle anything. In 200+ weddings, I've never missed a moment. But if something did happen, you're protected.

"Can we customize a package?"

Absolutely. These collections are starting points, not straitjackets. Tell me your plan and I'll tailor coverage, team size, and deliverables to fit. Let's talk.

Ready to See If We're a Good Fit?

I photograph 20–25 weddings per year to give every couple my full attention.
Peak season dates book 12–18 months in advance.

Jeff Award Winner · Former Steppenwolf Theatre Actor
151 Five-Star Google Reviews · Preferred Vendor: Chicago Winery & Cuneo Mansion
Fearless Photographers Member · WPJA Featured · Zola Best of 2025