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.

How much does Chicago proposal photography cost?

Proposal packages range from $750 to $1,100 depending on duration and location complexity. Most couples choose the $850 Signature package, which includes pre-planning consultation, the proposal coverage, 20-30 minute portrait session after, and 48-72 hour highlights delivery. All packages include hand-editing by me personally.

What if it rains on proposal day?

We pivot. I maintain a list of stunning covered backup locations (Garfield Park Conservatory, Union Station, hotel lobbies) and monitor weather closely. We confirm go/no-go status 4 hours before your planned time. Your surprise stays safe regardless of weather.

Chicago Proposal Photography

One satisfyingly sneaky moment.
We plan it together. I disappear.
They never see it coming.

Surprise proposal photographer in Chicago.
I handle timing, location, and logistics.
You focus on the ring. I capture the real thing
from a hidden position, then we take portraits after.

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

All include stealth planning + portraits after the yes

Start Planning

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