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 if we have a bold creative vision for our wedding photos?

You're my people. I live for couples who want something unexpected — whether that's elaborate themes, cinematic concepts, or 'what if we did something completely different' ideas. My fine art background and theater training mean I can help you execute ambitious creative visions while still making you feel comfortable in front of the camera. Let's design something unmistakably yours together.

What if we're camera-shy but also want creative photos?

That's not a contradiction — that's most of my favorite couples. Maybe you're introverts who are also massive Star Wars fans. Maybe you want romantic AND cinematic. My theater background helps you feel comfortable enough to forget the camera exists, AND my fine art eye ensures the images are gallery-worthy. You can absolutely have both.

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.

How do you keep a surprise proposal secret?

We plan everything in advance: a cover story for your partner, exact positioning, timing down to the minute. I arrive early, blend into the environment, and use a subtle signal so you know exactly when to walk into position. Your partner won't see me until after the YES.

What's the best time of day for a Chicago proposal?

Golden hour (1-2 hours before sunset) or sunrise for the most cinematic light. I scout the exact angle so your backdrop glows and your faces are beautifully lit. For indoor venues like The Ledge or restaurants, I adjust lighting recommendations based on the specific location.

What happens right after they say yes?

We take a short, natural mini-session nearby—usually 20-30 minutes of guided prompts that capture real emotion, zero stiff posing. This is often couples' favorite part: the pure joy right after the moment, photographed with the same cinematic quality.

How soon do we get our proposal photos?

Same-day sneak peeks (2-5 images) so you can share immediately. Full highlights gallery in 48–72 hours. Your complete curated gallery follows via Pic-Time within 1-2 weeks, all hand-edited—never AI or outsourced.

Where are the best proposal spots in Chicago?

Popular locations include Willis Tower Skydeck (The Ledge), 360 Chicago, Chicago Riverwalk, North Avenue Beach at sunrise, Lincoln Park's Honeymoon Bridge, Garfield Park Conservatory, Ping Tom Park with skyline views, rooftop restaurants, and private venues like Chicago Winery or Ella Elli. I help you choose based on your vision, timing, and crowd levels.

Can you do a last-minute or same-week proposal?

Yes—I accept proposals with as little as 48 hours notice when my schedule allows. Last-minute bookings are subject to availability, so reach out as soon as you know. Rush fee may apply for same-week requests.

Do you help with timing and lighting for Chicago proposals?

Yes—sunrise or golden hour is ideal. Jeremy scouts the exact angle so your backdrop glows and your faces are beautifully lit. He'll send you pins and timing recommendations based on the season and location.

How soon do we get proposal photos?

Same-day sneak peeks for immediate sharing, 72-hour highlights with your best images, and a full curated gallery delivered via Pic-Time within 1-2 weeks.

Where do you photograph proposals in Chicago?

Popular Chicago proposal locations include Willis Tower (The Ledge/Skydeck), 99th Floor Surprise, Chicago Riverwalk, North Avenue Beach, Lincoln Park (Honeycomb, South Pond), Garfield Park Conservatory, Ping Tom Park, Ella Elli, Chicago Winery, rooftops with skyline views, and private venues. Jeremy scouts any location in advance.

Chicago Proposal Photography

One satisfyingly sneaky moment.
Perfectly planned. Flawlessly captured.

Discreet positioning. Cinematic timing. The "yes" and everything after.

Packages from $750 | Most couples invest $850–$1,100

Plan Your Proposal

The Ledge · Skydeck · North Ave Beach · 151+ Five-Star Reviews

Chicago Proposal Photographer

Chicago proposal photographer delivering cinematic, candid images with zero stiff posing. My theater background means I know how to help nervous proposers feel calm and present—so you're focused on the moment, not the camera. I plan the spot, timing, and lighting, then capture the "yes" and natural portraits—fast, romantic, unmistakably you.

🏳️‍🌈 LGBTQ+ Welcoming • Multicultural Expertise • Sensory-Friendly Approach

Where we plan & photograph proposals

Willis Tower The Ledge / Skydeck
Chicago Riverwalk
North Avenue Beach
Lincoln Park (Honeycomb, South Pond)
Garfield Park Conservatory
Ping Tom Park
Ella Elli
Chicago Winery
Rooftops & skyline vantage points
Private venues & styled reveals

Not sure yet? I'll scout and send pins, timing-by-light, and a simple cover story to keep it secret.
And wherever your heart and my camera take us to capture your big moment!

Client Stories: Real Chicago Proposals

"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

"Jeremy planned a surprise proposal on the 99th floor of the Willis Tower. He is professional, kind, patient… and just fun! Photos were delivered early with extras."

Tiffany & Mike Sabev 99th-Floor Surprise Proposal, Willis Tower

Proposal Photography Collections

Choose the pace and coverage that fits your story—every option includes stealth planning, the moment itself, and natural portraits right after.

Essentials

$750 20 min

Exact position + timing-by-light
The YES + quick portraits
72-hour highlights

Book Essentials

Signature

$850 ~75 min

Location consult + pins
Reveal + mini portrait loop
72-hour highlights

Plan My Proposal

Cityscape

$950 ~1 hr 45 min

Skyline/rooftop vantage optimization
Multiple nearby portrait spots
72-hour highlights

Reserve Cityscape

Private Venue

$1,100 ~2.5 hrs

Private venue or styled set
Friends/family reveal options
72-hour highlights

Start Planning

All collections include a private Pic-Time gallery with downloads and optional print store.

Check Availability See Packages & Pricing

Proposal Photography — Quick Answers

How do we keep the proposal a surprise?

We plan a cover story, map the approach, and share pins. I arrive early, coordinate timing, and signal when to walk into position. Your partner will have no idea until you're down on one knee.

Do you help with timing and lighting?

Yes—sunrise or golden hour is ideal. I scout the exact angle so your backdrop glows and your faces are beautifully lit. I'll send you pins and timing recommendations based on the season.

What happens after the YES?

We take a short, natural mini-session (15–25 minutes) nearby. Whether you're camera-shy or want something creative, I use guided prompts for real emotion—zero stiff posing.

How soon do we get photos?

Same-day sneak peeks for sharing; 72-hour highlights; your curated gallery follows via Pic-Time within 1-2 weeks.

Where do you photograph proposals?

Willis Tower (The Ledge / Skydeck), 99th Floor Surprise, Chicago Riverwalk, North Avenue Beach, Lincoln Park, Garfield Park Conservatory, Ping Tom Park, Ella Elli, Chicago Winery, rooftops, and private venues.

What if I have a creative vision for the proposal?

I love that. Flash mob? Themed setup? Hidden musicians? My fine art background means I can help you execute ambitious ideas—not just document them. Tell me what you're imagining.

How much does Chicago proposal photography cost?

Packages range from $750 to $1,100. Most couples choose Signature ($850) for 75 minutes of coverage including location consultation and a mini portrait session after the YES.

Lock In Your Date View Wedding Collections