The Investment
Custom-designed experiences for every couple.
Every session at The Proposal Studios includes a personal planning consultation, naturally guided coverage, and a hand-edited gallery of full-resolution files. No AI software. No batch processing. Every image edited individually, by hand.
Every session is custom-designed around the couple, the location, and the moment you are trying to create. The structures below are starting points. Reach out and we will build something together.
Proposal Photography
ChicagoSurprise proposal photography anywhere in Chicago. We arrive early, stay hidden, and capture every genuine reaction from the first glimpse of the ring to the joyful yes. Highlights in your inbox within 48 hours. Our founder is a Jeff Award-winning actor with a credit at Steppenwolf Theatre Company, bringing a decade of stage and screen direction to every session.
Lead with the amount of time and planning support you need. We will land on the right fit together on a quick planning call. The Cinematic is the only collection with two photographers capturing simultaneous angles.
- Planning consultation and location guidance
- Discreet, hidden proposal coverage
- Portraits right after the yes
- Hand-edited gallery, full-resolution files
- Highlights within 48 hours
300+ proposals · Hand-edited · 48-hour highlights
- Everything in Collection 1
- Longer portrait session after the yes
- Room for phone calls home and unscripted moments
- Ideal for most Chicago locations
- Extended hand-edited gallery
300+ proposals · Hand-edited · 48-hour highlights
- Everything in Collection 2
- Expanded portrait session
- Two distinct Chicago locations
- Wardrobe change welcome
- Required for multi-location planning
300+ proposals · Hand-edited · 48-hour highlights
Two photographers. Two angles. One moment.
Jeremy plus a senior associate capturing two simultaneous angles. A proposal happens in a fraction of a second. Two angles means certainty.
Best for high-design or once-in-a-lifetime plans where the moment deserves dual coverage and faster turnaround.
- Two senior photographers on the moment
- Two simultaneous angles during the proposal
- 2.5 hours of total coverage
- Multi-location flexibility built in
- 48-hour highlight delivery, faster final gallery
Limited senior associate availability · Book early
Have a vision that does not fit any of these? Reach out anyway. Private venues, destination proposals, larger productions, and fully styled sessions can all be designed around your specific goals.
Enhancements: Rush full gallery within 72 hrs $225 · Champagne service $135 · Proposal films inquire · Private venues and destinations inquire
50% retainer to reserve your date. Balance due upon gallery delivery.
Engagement Photography
ChicagoRelaxed, cinematic sessions designed to capture your relationship as it actually is. Natural guidance means you will feel like yourselves, not models. Every image hand-edited individually within 10 days.
- 1.5-hour cinematic session
- One or two Chicago locations
- Naturally guided for genuine comfort
- 50-70 hand-edited images
- Full-resolution digital files
- Online gallery with print shop
- Gallery delivered within 10 days
Hand-edited · 10-day delivery · 5.0★ rating
- 2-hour extended cinematic session
- Multiple Chicago locations
- Wardrobe change welcome
- Naturally guided for genuine comfort
- Extended hand-edited gallery
- Full-resolution digital files
- Online gallery with print shop
- Gallery delivered within 10 days
Hand-edited · 10-day delivery · 5.0★ rating
Have a vision that does not fit either of these? Reach out anyway. Sunrise sessions, destination engagements, larger productions, and fully styled shoots can all be designed around your specific goals.
Enhancements: Rush delivery within 72 hrs $200 · Sunrise session $195 · Already a Proposal Studios client? Ask about your exclusive engagement credit.
50% retainer to reserve your date. Balance due upon gallery delivery.
Skip the separate engagement session.
Our Collection 3 proposal session at $985 includes 1 hour 45 minutes of cinematic portrait time across two Chicago locations with a wardrobe change welcome. The surprise moment plus a full engagement shoot, all in one. It is the best value if you are planning both. Ask about this option when you reach out.
Ask about the combination option →Questions about pricing
What is included in every session?
Every session includes a personal planning consultation, location guidance, naturally guided coverage so you feel completely comfortable in front of the camera, a hand-edited gallery of full-resolution digital files, and an online gallery with print shop access. No AI software, no batch processing, no shortcuts.
How is each session designed?
Every session is custom-designed around the couple, the location, and the moment you are trying to create. The structures shown above are starting points. Anything can be refined to fit your specific vision. Reach out and we will build something together.
What is The Cinematic and why is it different?
The Cinematic is the only collection with two photographers. Jeremy plus a senior associate capture two simultaneous angles during the proposal moment. A proposal happens in a fraction of a second. With one photographer, you get one angle. With two, you get certainty. It is the right fit for high-design proposals, elaborate plans, premium venues, or anyone who wants the most coverage possible during the actual moment.
Is there a discount for booking both a proposal and an engagement session?
Yes, in two ways. Our Collection 3 proposal session at $985 includes 1 hour 45 minutes of cinematic portrait time across two locations, effectively replacing a separate engagement session. And if you book separately, Proposal Studios clients receive an exclusive engagement credit. Ask about both options when you reach out.
Do you offer rush delivery?
Yes. Rush delivery of your full gallery within 72 hours is available for $225 on proposal sessions and $200 on engagement sessions. Proposal highlights (a curated selection perfect for sharing immediately) are always delivered within 48 hours at no extra charge. The Cinematic includes 48-hour highlights and an expedited final gallery as standard.
What are the payment terms?
A 50% retainer is due to reserve your date. The balance is due upon gallery delivery. We accept all major credit cards and digital payments.
Jeremy, we love your style and approach. Can we hire you for our wedding as well?
Absolutely. The Proposal Studios is the sister brand of Jeremy Glickstein Photography, an award-winning Chicago wedding photography studio with 151+ five-star Google reviews and Best of ZOLA recognition for 2025 and 2026. Many of our proposal couples continue with us for engagement sessions and wedding day coverage. Proposal and engagement clients also receive an exclusive credit toward wedding photography. Same creative vision, same hand-edited care, from the first surprise to the last dance.
From the proposal to the last dance.
The Proposal Studios is the sister brand of Jeremy Glickstein Photography. Proposal and engagement clients receive an exclusive credit toward wedding coverage. Same creative vision, same hand-edited care, from the first surprise to the final toast.
Start the ConversationWedding photography by Jeremy Glickstein Photography