How much do couples typically invest?

Weddings: $5,500–$11,000. Most couples land at $7,000–$9,500 for Jeremy-led coverage with two photographers, 48-hour highlights, and hand-edited galleries. Associate-led collections start at $5,500. Proposals: $750–$1,100. Engagements: $750–$1,050.

How fast will we get photos?

Highlights: 24–72 hours depending on collection. Full gallery: 3–5 weeks, hand-edited by me. Never rushed, never outsourced.

We want great photos but we are self conscious and feel a little scared about not looking good. Will this be awkward?

About 70% of my couples say exactly this. I spent 10+ years as a professional actor, director, and acting coach—including work at Steppenwolf Theatre Company and a Jeff Award. I give you something real to do. You'll be so focused on each other, you'll forget I'm there. That's when the magic happens.

What does your theater background actually do for us?

Three things: 1. I know how it feels to be on camera. 2. I read energy and adapt. 3. I find the moments. You're not performing. You're living your day while I use 10+ years of experience to help you look and feel like yourselves.

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

Jeremy-led: I'm your primary photographer. $7,000–$11,000. Associate-led: One of my personally selected and trained photographers leads your day. Same artistic direction and editing style—because I edit every single gallery myself. $5,500–$7,750.

Our venue has terrible lighting. Is that a problem?

No. I thrive in low light. Professional gear, mastery of ambient light, and years of shooting in dark churches, candlelit receptions, and nighttime ceremonies. I bring subtle professional lighting your guests won't even notice.

Our venue isn't very photogenic. Can you still make it look good?

There are no boring venues—only boring photographers. I started as a fine art street photographer—I find beauty in unexpected places. Your venue becomes a canvas. I find the light, the angles, the textures. Trust the process.

Do you travel for weddings?

Yes—Chicagoland, Midwest, and destination weddings worldwide. Travel fees apply outside the Chicago area. Share your plans and I'll send a tailored quote.

How do proposal sessions work?

I handle everything: location scouting, timing by light, hidden positioning. I'm in place before you arrive—invisible until after the 'yes.' Then we celebrate with portraits. Highlights delivered within 48–72 hours. Last-minute requests welcome—I accommodate proposals with as little as 48 hours notice.

JEREMY GLICKSTEIN PHOTOGRAPHY
PREFERRED PHOTOGRAPHY & VIDEOGRAPHY VENDOR AT:

Chicago Winery Wedding Photography & Videography

Soulful, cinematic photo & video crafted specifically for Chicago Winery — from candlelit vows to skyline portraits. My theater background means camera-shy couples feel at ease in the dramatic Barrel Room lighting.

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🏆 Jeff Award Winner 🎭 Former Steppenwolf Theatre 📸 Fearless Photographers

Quick Answer: Chicago Winery Weddings

Typical investment: $6,500–$8,100 for 8–10 hours of coverage (photo), with venue-ready lighting and a rain-safe portrait plan.

Lighting realities: warm, low-light ceremony—fast primes + off-camera flash for clean skin tones.
A stress-proof timeline that works: Barrel Room portraits + Atrium transitions with buffer windows so you stay present.
Delivery: same-week highlights for family & vendors; full gallery delivery per your contracted timeline.

Why couples feel at ease here

10+ years as an actor and director at Steppenwolf Theatre taught me how to help camera-shy couples forget the lens exists — even in the dramatic Barrel Room lighting. Instead of "smile at the camera," I give you something real to do. You'll feel like yourselves.

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About Chicago Winery

In River North, Chicago Winery blends the romance of a working winery with modern architecture — dramatic Barrel Room, sculptural ceremony arches, and rooftop skyline views. Hotels, restaurants, and nightlife are a short walk, making it guest-friendly and effortless.

Signature spaces: the intimate Barrel Room, elegant ceremony site, and a spacious reception hall with warm arches.
Guest-friendly access: elevator, nearby parking, easy hotel blocks.
Food & wine: on-site culinary team and pairings designed for celebration.
Photo flexibility: natural window light by day, ambient glow by night, skyline looks at dusk.

Ceremony arches with candlelight at Chicago Winery wedding

Chicago Winery Wedding Photography & Videography — Highlights

A quick look at the venue's aesthetic — Barrel Room warmth, ceremony arches, and editorial portraits.

Kim & Brad's Chicago Winery Mini-Story

A warm arc from early moments to the last toast — with signature Barrel Room frames. Click any image to view full-size.

Chicago Winery wedding closing portrait at night—cinematic editorial finish — Closing portrait.

Dance floor celebration at Chicago Winery wedding reception — Dance floor energy.

Barrel Room silhouette portrait at Chicago Winery wedding—dramatic backlit shot — Barrel Room silhouette portrait.

Quiet moment in the Barrel Room at Chicago Winery—intimate couple portrait — Quiet moment in the Barrel Room.

Editorial Barrel Room portrait at Chicago Winery wedding—fine art style — Editorial Barrel Room portrait.

Wedding details and dress at Chicago Winery before ceremony — Details before the ceremony.

Champagne tower moment on the patio at Chicago Winery wedding — Champagne tower moment on the patio.

Ceremony framed by warm architectural arches at Chicago Winery — Ceremony with warm arches.

Black and white Barrel Room portrait at Chicago Winery wedding—classic artistic style — Black & white Barrel Room portrait.

Mystical Barrel Room portrait at Chicago Winery with dramatic lighting and atmosphere — Mystical Barrel Room portrait.

Tender embrace in the Barrel Room at Chicago Winery wedding—romantic moment — Tender embrace in the Barrel Room.

Fine art couple's portrait shot through the fireplace at Chicago Winery wedding — Fine art couple's portrait shot through the fireplace.

Patio portrait with bride smiling at Chicago Winery wedding—natural light — Patio portrait, bride smiling.

First look on the staircase at Chicago Winery in black and white—emotional moment — First look on the staircase (B&W).

Kim & Brad — Wedding Films

Cinematic storytelling that pairs with their gallery — the Winery's glow in motion.

Chicago Winery FAQ (Photos & Timeline)

How much photography time do we really need here?

Most couples book 8–10 hours. The extra buffer helps with Barrel Room portraits and smooth room flips.

Is flash allowed during the ceremony?

I plan for no-flash ceremony coverage unless your officiant confirms otherwise; my low-light primes keep skin tones clean.

Best places for portraits if it rains?

Barrel Room staircase, interior arches, and covered entry within ~100 ft—zero-stress, weather-proof options.

What if we're awkward in photos?

Most of my couples tell me they hate being photographed. My theater background means I give you something real to do — not stiff poses. You'll feel like yourselves, and the Barrel Room shots will blow you away.

How soon do we see photos?

Same-week highlights; full gallery delivery per your contract timeline.

Can you coordinate with our planner/band?

Yes—timeline and lighting cues are shared in advance so speeches and first dance are perfectly lit.

Do you also offer video?

Yes—cinematic add-on crafted for the Winery's look, with natural audio and matching color profile.

Do you edit your own photos?

Every single image. Hand-edited by me, never AI, never outsourced. Your gallery has consistent artistic vision from first look to last dance.

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Learn more: Chicago Wedding Photography · Full FAQ · Investment & Packages

Preferred Vendor at Chicago Winery | 151+ Five-Star Reviews | Featured on Style Me Pretty

"We HATE being photographed, but Jeremy made us forget he was there. The Barrel Room shots blew us away — we look like ourselves, just... dreamy."
— Kim & Brad, Chicago Winery 2024

📅 Now booking 2026 Chicago Winery weddings — Only 3 prime Saturdays remaining

Your Chicago Winery Wedding Investment

Transparent, tailored coverage with photo + video crafted for the Winery's lighting and flow.

Wedding Photography Collections: from $6,500
Cinematic Wedding Videography: custom add-on
Engagement Sessions: $600 when bundled with wedding coverage

Every image hand-edited by me. Never AI. Never outsourced.