Chicago • Skyline • Rooftops • Landmarks
Chicago Proposal Photography — Discreet. Timed. Cinematic.
One chance, perfectly planned. I scout the exact spot, lock timing to the minute, cue your position—and capture the "yes," then craft elevated, artful portraits after. Quality-first, never factory edits.
Led by a former professional actor & director—cinematic direction, real emotion, zero forced moments.
★★★★★ "They're all fantastic… we're blown away. It's beautiful work." — Carlos Frias
Chicago proposal photographer delivering cinematic, candid images with zero stiff posing. 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
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!”
“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.”
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
- Exact position + timing-by-light
- The YES + quick portraits
- 72-hour highlights
Signature
- Location consult + pins
- Reveal + mini portrait loop
- 72-hour highlights
Cityscape
- Skyline/rooftop vantage optimization
- Multiple nearby portrait spots
- 72-hour highlights
Private Venue
- Private venue or styled set
- Friends/family reveal options
- 72-hour highlights
All collections include a private Pic-Time gallery with downloads and optional print store.
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.
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.
What happens after the YES?
We take a short, natural mini-session (15–25 minutes) nearby—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.
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.
