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 Photography

Just be yourselves. We'll make photos that look and feel like a dream.

Camera-shy or creatively bold, you're in the right place. Cinematic, painterly, true.

151+ Five-Star Reviews
Two Photographers Included
24-72 Hour Highlights
Romantic Chicago wedding photography featuring couple in soft natural light
300+ Proposals · 250+ Weddings 151+ Five-Star Reviews Best of Zola 2025 & 2026 Preferred Vendor: Chicago Winery
Actor, Acting Coach & Director · Steppenwolf Theatre Company Credit Jeff Award Winner

Chicago Proposal & Wedding Photographer

Your Heirloom Awaits

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

From the question to the vows: cinematic, painterly galleries hand-edited personally by Jeremy.

10+ years as an actor, acting coach, and director. Jeff Award winner, with a Steppenwolf Theatre Company credit. A decade of fine art street photography before ever touching a wedding. 8 years as a professional wedding photographer and 250+ weddings captured.

You'll feel comfortable. Your photos will be cinematic and frame-worthy. That's the whole point.

Investment Overview

Clear collections for proposals, weddings, and engagements. Lead with the coverage that fits, and we shape the details together.

  • Proposals

    $795 to $1,795

    Four Collections. The Cinematic at $1,795 brings two photographers for editorial-quality coverage.

    Plan Your Proposal

  • Weddings

    $5,975 to $7,500

    Three collections, two photographers on every one. Most couples invest $6,750.

    Learn More

  • Engagements

    $750 to $950

    Three sessions. Cinematic portraits, natural guidance, frame-worthy and real.

    View Sessions

Every Collection

18 weddings. That's it. Peak season books 12 to 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.

Comfort-Based Guidance

A decade in theater, including a Steppenwolf Theatre Company credit, taught me how to help people relax on camera. Natural guidance, not stiff poses. No "say cheese." Just you.

Fast Highlights

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

Hand-Edited Galleries

Every wedding and proposal image edited personally by Jeremy. That's how the cinematic look stays consistent across every gallery.

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."

Verified Wedding Client

Proposal Photography

Discreet coverage, perfect timing, iconic Chicago backdrops.

300+ proposals captured since 2019. We position before you arrive, invisible until after the yes. Then we celebrate with portraits at your chosen location. Four Collections built around how much coverage, how many locations, and whether you want one photographer or two. See how we capture proposals.

Proposal Collections

One photographer through Collection III. Two on The Cinematic.

Collection I

$795
  • 30 minutes of coverage
  • One location
  • One photographer

Focused coverage of the moment, plus portraits after the yes.

Inquire

Collection II

$895
  • 60 minutes of coverage
  • Walkable location flexibility
  • One photographer

More time, and the freedom to move to a nearby spot.

Inquire

Collection III

$985
  • 90 minutes of coverage
  • Multi-location capability
  • One photographer

Multiple locations and a fuller portrait session.

Inquire

The Cinematic

$1,795
  • 150 minutes of coverage
  • Two photographers, two angles
  • Multi-location flexibility
  • 24-hour highlights

Two photographers for the moment that only happens once.

Inquire

The Cinematic Proposal · $1,795

Two photographers. Two simultaneous angles. One unrepeatable moment.

A proposal happens once. The Cinematic exists because some moments deserve coverage from more than one perspective.

Jeremy plus a senior associate

Jeremy leads creatively. A senior associate captures the moment from a second angle. Both photographers brief together pre-session so the coverage is coordinated, not chaotic.

150 minutes of coverage

Pre-proposal moments, the moment itself, family or friend reveals, and editorial portraits at your chosen location. Multi-location flexibility built in.

Expedited delivery

24-hour highlights (vs 48 to 72 hours standard). Final hand-edited gallery within 5 days (vs 5 to 7 days standard). Share the news while it's still fresh.

Senior-only staffing

No junior second shooters at this tier. The Cinematic books only when a senior associate is available. That structural scarcity is part of what makes the product different.

For couples planning high-design proposals at premium venues, or anyone whose vision deserves a larger visual treatment. Subject to senior associate availability.

What's Included in Every Collection

Planning Support

Full consultation on location, timing, logistics, and positioning. We handle the details so you can focus on the question.

Discreet Coverage

Pre-scouted angles and a text-signal system. You send a text when you're close. We're already in position.

Portraits After the Yes

Natural, comfort-based guidance from a former actor, acting coach, and director. Comfortable, real portraits.

Hand-Edited Gallery

Every proposal image edited personally by Jeremy. Full-resolution files with print rights.

Highlights Within Days

Curated set delivered within 48 to 72 hours (24 hours for The Cinematic) so you can share the news while it's still fresh.

Full Gallery

Complete hand-edited collection via private gallery with full-resolution downloads. 5 to 7 days standard, 5 days for The Cinematic.

"Proposing can be a stressful thing and Jeremy helped me nail down the best location and time. He communicated throughout the entire process, up to a few minutes before letting me know he was ready. The pictures came out better than I could have expected."

Verified Google Review · Read more reviews

Wedding Photography

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

Wedding Collections

$5,975 to $7,500

Most couples invest $6,750. Two photographers, every wedding.

"Three collections, each with two photographers. We find the right one for your day."

Wedding Collections

Two photographers on every one.

Collection I

$5,975
  • 8.5 hours of coverage
  • Two photographers included
  • Hand-edited gallery by Jeremy
  • Timeline planning and full print rights

Intimate celebrations and tighter timelines.

Inquire

Collection II

$6,750
  • 9.5 hours of coverage
  • Two photographers included
  • Hand-edited gallery by Jeremy
  • Timeline planning and full print rights

A full day, getting ready through the send-off.

Inquire

Collection III

$7,500
  • 10.5 hours of coverage
  • Two photographers included
  • Hand-edited gallery by Jeremy
  • Timeline planning and full print rights

Longer days, larger celebrations, more coverage.

Inquire

Most couples invest $6,750. Every collection is complete as built: tell me what your day looks like and I will point you to the one that fits.

What's Included

Every collection starts with these essentials

Hand-Edited Personally by Jeremy

Every wedding image, every gallery, delivered in a private gallery with full print rights. That's how the cinematic, painterly look stays consistent.

Comfort-Based Guidance

From a former actor, acting coach, and director. No stiff poses. No "say cheese." I give you something real to do so you'll forget I'm there.

Timeline Strategy

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

Two Photographers, Every Wedding

While one of us is on the candid moments your guests are living, the other is on you two. Complete coverage is the standard, not an upgrade.

Fast Highlights

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

Backup Everything

Dual card slots. Backup equipment at every shoot. 250+ weddings, zero missed moments.

Choosing Your Collection

What shapes the right fit

Coverage Hours

Collections run 8.5 to 10.5 hours. Your timeline points to the right one

💍

Engagement Session

Book a session before the wedding so the camera already feels easy on the day

Delivery Speed

Highlights land in 24 to 72 hours depending on collection

📷

Team Size

Two photographers standard. A third is available for large guest lists or multi-venue days

The one extension: a third photographer at $300/hr for large guest lists or multi-venue days. Everything else is already in the collection. Engagement sessions are booked separately ($750 to $950).

How It Works

1

Connect

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

2

Choose Your Collection

Pick the collection that fits your day. The details get shaped together after.

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 find your collection.

Engagement Sessions

Cinematic portraits with natural guidance. 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. Professional editing, painterly light, sublime results. See sessions.

Collection I

$750
  • 1 hour
  • Natural, comfort-based guidance
  • Hand-edited gallery by Jeremy
  • Session planning
  • Private gallery with print rights

Clean, cinematic portraits at a location that means something to you.

Inquire

Collection II

$850
  • 1.5 hours
  • Natural, comfort-based guidance
  • Hand-edited gallery by Jeremy
  • Session planning
  • Private gallery with print rights

More room for variety with a longer photo walk, movement, and a less rushed session.

Inquire

Collection III

$950
  • A little over 2 hours
  • Natural, comfort-based guidance
  • Hand-edited gallery by Jeremy
  • Session planning
  • Private gallery with print rights

A robust session with an extended walk and the option to change locations by car. Perfect for couples planning a wardrobe change and a more curated set.

Inquire

Not sure which session fits? Tell me about your shoot and I'll point you to the right one.

"We had a great time getting creative and capturing our relationship through his photography. Jeremy is a person who is passionate about his craft. We couldn't be happier with the results."

Kassy and Tyler, Engagement Session · View portfolio

Additional Options

  • Engagement sessions (booked separately): $750 to $950
  • Third photographer: $300/hr

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 as an actor, acting coach, and director, learning how to help real people relax on camera. 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. More on my approach.

"How do you determine pricing for weddings?"

Three collections from $5,975 to $7,500. Two photographers are included on every collection. Collections run 8.5 to 10.5 hours, and most couples invest $6,750. After we talk about your specific day, I'll point you to the collection that fits.

"Is a second photographer included?"

Yes. Every wedding includes two photographers. While one of us covers the candid moments your guests are living, the other stays on you two. Complete coverage is the standard here, not an upgrade. A third photographer is available for large guest lists or multi-venue days.

"What is The Cinematic and why does it cost more?"

The Cinematic is the two-photographer proposal at $1,795. Jeremy plus a senior associate shoot together, capturing two simultaneous angles of the same moment. Coverage runs 150 minutes instead of the standard 30 to 90. Multi-location flexibility is built in. Highlights deliver in 24 hours (vs 48 to 72 hours standard) and the final gallery in 5 days (vs 5 to 7 days standard). It books only when a senior associate is available, which is part of what makes the product different. Most couples don't need this tier. For those who want spectacle, it exists.

"How is proposal photography priced?"

Four Collections from $795 to $1,795. Collection I ($795) covers 30 minutes of focused proposal coverage. Collection II ($895) extends to 60 minutes with walkable location flexibility. Collection III ($985) covers 90 minutes including multi-location capability. The Cinematic ($1,795) brings two photographers for 150 minutes of editorial coverage. Tell us about your proposal and we'll recommend the right Collection.

"How are engagement sessions priced?"

Three sessions, $750, $850, and $950, scaling by how much time you want. Tell me about your shoot and I'll recommend the right fit.

"Why are you more expensive than some photographers?"

I personally hand-edit every wedding and proposal gallery. Every wedding includes two photographers. I limit my calendar to 18 weddings a year so each couple gets full attention from planning through delivery. That's a different product than volume photography. The Cinematic tier exists because some moments warrant a larger production, but my couples get exactly what they need from the core collections.

"What's your background?"

10+ years as a professional actor, acting coach, and director, with a Steppenwolf Theatre Company credit. Jeff Award winner. IMDb credits. A decade of fine art street photography before ever touching a wedding. That background taught me how to help people reveal their authentic selves on camera. Full story.

"When do we get our photos?"

Wedding highlights: 24 to 72 hours depending on collection. Wedding full gallery: 3 to 5 weeks. Proposal highlights: 48 to 72 hours (24 hours for The Cinematic). Proposal full gallery: 5 to 7 days (5 days for The Cinematic). Engagement gallery: 7 to 10 days. 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.

"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. 250+ weddings, zero missed moments.

"Can we customize a collection?"

Every collection is complete as built: two photographers, a hand-edited gallery, timeline strategy, and full print rights. The one extension is a third photographer at $300/hr for large guest lists or multi-venue days. Tell me what your day looks like and we will shape the details once your date is secured. Let's talk.

Let's See If We're Right for Each Other

18 weddings a year. Peak season books 12 to 18 months out.

300+ Proposals Captured · 250+ Weddings Photographed
Jeff Award Winner · Steppenwolf Theatre Company Credit
151+ Five-Star Reviews · Best of Zola 2025 & 2026
Preferred: Chicago Winery

Chicago Venues I Know

250+ 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

Outdoor

  • North Avenue Beach: Skyline reflections, golden hour
  • Alfred Caldwell Lily Pool: Hidden gem, prairie serenity
  • Chicago Riverwalk: Urban energy, architectural backdrops
  • Ping Tom Memorial Park: Pagoda pavilion, river walkway, skyline angles
  • Milton Lee Olive Park: Lakefront skyline without the Navy Pier crowds
  • 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, and rooftops with skyline views 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.

Guidance That Doesn't Feel Like Guidance

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 added).

Wedding Day

I arrive early. Scout light. Stay steady 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 to 700+ 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

250+ weddings. These come up every time.

"We're not photogenic."

Most people feel this way. I use movement-based guidance 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. Steady, 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?

Check Your Date

Tell me about your day and we'll build the right collection. It starts with a quick note.