Chicago • Non-Traditional • Collections Begin at $6,500

Chicago Wedding, Proposal & Engagement Photography

Wedding Photography That Looks and Feels Like a Good Dream

The kind of dream you want to have again and again—romantic, surreal, unmistakably yours. I'm your creative director with a camera: former Chicago actor/director/street photographer. I know both sides of the lens. Natural direction, sublime moments. I find light and beauty everywhere—from urban romance to forest fantasies. Signature Vision Weddings for all the lovers.

I'm your dream weaver.

  • Shepherd for the camera shy
  • Hype man for the life of the party
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"We had the BEST experience working with Jeremy. He made our vision come to life & even trekked through a forest to get our dream photos." — Alyssa & Danny
Preferred Vendor: Chicago Winery • 145+ ★★★★★ Reviews • Fearless & WPJA Member • 🏳️‍🌈 LGBTQ+ Welcoming
Weddings Proposals Engagements
Lyric Opera of Chicago wedding portrait—multicultural couple on stage in dramatic cinematic lighting

As Seen In / Trusted By

Fearless Photographers Member badge Wedding Photojournalist Association Member badge Featured on Equally Wed badge Best of Zola Award badge 145+ ★★★★★ Reviews

Your Creative Director's Approach

Most wedding photographers show up and shoot. I plan scenes, direct moments, and create a visual story that feels like you—not a cookie-cutter Pinterest board.

"Jeremy treats the session as a casual hang that allows any anxiety to melt away. It was an absolute joy to walk around and spontaneously snap pictures when he found a nicely lit nook or environment. The finished product was perfection." — Jason Babinsky
01

Pre-Production Call

We talk about your vision, your vibe, and what makes you uncomfortable. I scout locations if needed. This isn't an intake form—it's a creative collaboration.

02

Shot List + Storyboard

I create a loose shot list based on your must-haves and my directorial instincts. Think: "moody forest portraits at golden hour," not "bride and groom by tree #47."

03

Day-Of Direction

I guide you through natural movements and interactions—not stiff poses. You'll feel like you're in a scene, not a photoshoot. Camera-shy couples especially love this.

04

48-Hour Highlights

The best 20-30 shots in your inbox within 48-72 hours. Full gallery in 4-6 weeks. You're not waiting months to relive your day.

Why Couples Feel Relaxed With Me

With professional roots as an actor and director, I know both sides of the camera—guiding natural movement, reading energy, and pacing moments so you feel present (not posed).

Years of directing and performing taught me how to draw out real emotion and connection—so your images feel like an authentic reflection of you, not a staged version.

  • Calm, clear direction when you want it; quiet observation when it counts.
  • Camera-shy friendly: gentle prompts that feel natural, never stiff.
  • Cinematic storytelling: emotion first, trend-proof, creative portraits second.

Why Our Couples Keep Coming Back (And Bringing Their Friends)

Camera-Shy?

We specialize in making you comfortable

"Jeremy was very kind and helped me feel comfortable with being photographed, which is a big deal. The pictures were so creative and each one looked like something from a movie. Easily the best pictures of my life." — Gabi F.
Fast Delivery

Highlights in 48-72 hours, not weeks

"He gave us the finished edited photos early, and included a few extras. Jeremy is professional, kind, patient (huge plus for someone like me haha), and just fun!" — Tiffany W.
Non-Traditional

When your vision doesn't fit the mold

"He is so considerate, professional, and easy to talk to. He is incredibly creative and motivated to make our dreams come to life. He was even willing to hike in a forest with us on a hot, buggy evening to capture the most beautiful photos we've ever seen." — Alyssa & Danny

What Couples Say

Real notes from real celebrations

"Jeremy, thank you again for all your help and diligence, and for making our wedding day unforgettable! We couldn't be happier with how everything turned out, and we can't thank you enough for being there for us. We love the shots!"

— Jen & Kirill • The Rookery Building

"We couldn't be happier with our engagement photoshoot experience with Jeremy! He did an absolutely fantastic job capturing my fiancé Kristine and me in some of Chicago's most iconic locations… Thank you for giving us memories we'll treasure forever, Jeremy!"

— Kristine & Nick • River North & Chicago Winery

"Jeremy was a pro to work with. He scouted the location weeks in advance to set up a surprise shot and made use of every last minute of our time. He made some beautiful images — they speak for themselves!"

— Carlos Frias (James Beard award-winning journalist) & Gaby • Skydeck, Willis Tower

145+ Five-Star Reviews Verified Across:

Google ★★★★★ 104 reviews Yelp ★★★★★ 6 reviews Zola ★★★★★ 7 reviews Facebook ★★★★★ 11 reviews Trustpilot ★★★★★ 16 reviews
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Fine art Chicago wedding photographer captures intimate bride and groom laying together in cinematic portrait.
Cinematic Chicago wedding photography with dramatic lighting inside industrial barrel room at Chicago Winery.
Bride in white gown in front of rustic barn at Chicago suburb countryside wedding.
Modern black tie Chicago wedding portrait with bride and groom separated by glowing light panels.
Silhouette of couple framed by Chicago city skyline through architectural window.
Engagement-style photo of couple in autumn at Ping Tom Park.
Bride and groom sharing a quiet moment in golden hallway, Chicago wedding photographer Jeremy Glickstein.
Candid outdoor Chicago wedding moment with bride and groom leaning against wal with interesting light patter cascading in fine art style.
Romantic cinematic Chicago wedding kiss in dramatic modern hallway.
Bride illuminated against Byzantine-style icons in Wisconsin Monastery.
Romantic fine art wedding portrait of bride and groom seated on garden bench near ivy wall.
Cinematic couple’s portrait framed by historic Chicago architecture at sunset.

Why Couples Choose Jeremy Glickstein Photography

Unmistakably You—Not a Template

We build around your story and aesthetic so the work feels singular. Editorial polish, human heart—never cookie-cutter.

Calm Direction, Real Moments

Camera-shy friendly. Natural direction that looks effortless on camera, with space for genuine emotion.

Two Photographers, Every Angle

Seamless coverage with quick highlights and confidence in any venue, any light.

Fearless & Inclusive

Bold vision with honest emotion—LGBTQ+, interfaith, and multicultural celebrations welcome.

Painterly Backdrops

Urban romance to dreamy gardens—timed by light and tailored to you. Explore a recent Chicago proposal.

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Frequently Asked Questions

How much do couples typically invest in wedding photography?

Most wedding collections range from $6,500–$8,150 and include two photographers for full-day, cinematic coverage with 48-72 hour highlights. Proposals start at $750; engagements are $750–$1,050.

How fast will we see our wedding photos?

You'll receive 48–72 hour highlights perfect for sharing with family and vendors. Full galleries follow on your promised delivery timeline—never rushed, always refined.

Do you help plan proposals and sessions?

Yes. Location scouting, timing-by-light, and subtle coordination so it unfolds naturally and beautifully. I stay hidden during proposals and capture every genuine emotion.

Do you travel for weddings?

Yes—Chicagoland, Midwest, and destination weddings worldwide. Share your plans for a tailored quote. Travel fees apply for destinations outside the Chicago area.

We're camera-shy. Can you help?

Absolutely. My actor/director background means I know how to make people comfortable on camera. Gentle direction, natural movement, and authentic moments—never stiff or awkward posing.

How does your actor/director background help us?

I know both sides of the lens. I direct scenes like a film director—blocking movement, reading light, anticipating emotion—but it feels natural, not staged. You get cinematic imagery without the stress.

What do we receive after our wedding?

48-72 hour highlights, full edited gallery (typically 500-700 images for weddings), high-resolution digital files with print rights, and an online gallery for easy sharing with family and friends.

How does booking work?

Simple e-contract and retainer secure your date. Flexible payment plans available (2-3 installments). Final balance due before your wedding day. We handle all logistics and coordination.

What about weather and reschedules for proposals?

We plan with weather fallbacks. If conditions shift, we move to a covered or alternate spot quickly. The moment stays stress-free and perfectly captured.

Do you handle photo permits and location logistics?

Yes. We guide you on permits (parks, rooftops, landmark lobbies), timing to avoid crowds, and venue coordination. We handle all scouting and logistics in advance.

Are albums and prints available?

Heirloom albums, framed prints, and parent books are available à la carte or bundled with collections. Design help included. Ask about premium Italian albums during booking.

Jeremy Glickstein Photography

Cinematic with Soul — For Couples Who Want More Than Typical Photos

I create cinematic, painterly photography with true color and honest emotion—photojournalistic in spirit, elevated in style. Proposals planned to the minute. Engagements timed by light. Weddings documented with two photographers, so nothing is missed.

48–72 hour highlights • Inclusive & multicultural expertise • Calm direction, zero stiff posing

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Cinematic Wedding & Proposal Reel

Our videography captures the same painterly light and soulful honesty as our photography— weaving vows, laughter, and fleeting moments into a cinematic story you'll replay for decades.

Based in Chicago, we create wedding and proposal films with cinematic storytelling and painterly visuals. From intimate elopements to full-day celebrations, our videography blends natural sound, authentic emotion, and editorial polish—crafted to feel timeless and unforgettable.

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