The Investment
Custom-designed experiences
for every couple
Every session at The Proposal Studios includes a personal planning consultation, naturally directed coverage, and a hand-edited gallery of full-resolution files.
Every image edited individually, by hand. No batch processing.
Every session is custom-designed around the couple, the location, and the moment you're trying to create. The structures below are starting points. Reach out and we'll build something together.
chicago proposal photography
Proposal Photography
Surprise 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 Steppenwolf Theatre Company credit. A decade of stage and screen experience shapes every session. You'll feel directed without being told what to do, and looked after without anyone hovering.
300+ proposals · Hand-edited · 48-hour highlights
$825
Single-Location Session
Best for couples who want the proposal moment captured cleanly and a focused portrait window after.
- Planning consultation and location guidance
- Ccovert proposal coverage
- 30 minutes of portraits at the proposal spot
- Hand-edited gallery, full-resolution files
- Highlights within 48 hours
- Full gallery in 5 to 6 days
$895
Extended Single-Location Session
Best for couples who want extended portrait time at a single location, with breathing room for phone calls and unscripted moments.
- Everything in the single-location session
- 60 minutes of portrait time
- Room for phone calls home and unscripted moments
- Extended hand-edited gallery
- Images curated for save-the-dates
- Highlights within 48 hours
$1095
Two-Location Session
Best for couples who want two locations and the most variety in their final gallery.
- Everything in the extended session
- 75-90 minutes of portrait time
- Two distinct Chicago locations
- Wardrobe change welcome
- Same-day sneak peek delivery
- Ideal for couples skipping a separate engagement session.
The Cinematic Price
Some proposals deserve more than one perspective. The Cinematic pairs Jeremy with a senior member of our team, two photographers working in concert, capturing the moment from two angles at once. One frames the wide cinematic scene. The other stays close on the faces, the hands, the tears.
Two and a half hours. Multiple locations if you want them. The freedom to move through the city without watching the clock.
This is our most complete proposal experience, built for plans that have been months in the making and deserve to be remembered in full. Because of the senior staffing it requires, availability is limited.
$1,795
Reach out anyway. Private venues, destination proposals, larger productions, and fully styled sessions can all be designed around your specific goals.
Building something bigger?
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.
chicago engagement photography
Engagement Photography
$895
1.5-Hour Single-Location Session
Relaxed, cinematic sessions designed to capture your relationship as it actually is. Natural direction means you'll feel like yourselves, not models. Every image hand-edited individually within 10 days.
Best for couples who want a focused session at one meaningful location, with room to relax into it.
- 1.5-hour cinematic session
- One or two Chicago locations
- Naturally directed for genuine comfort
- 50-70 hand-edited images
- Full-resolution digital files
- Online gallery with print shop
- Gallery delivered within 10 days
$1095
2-Hour Multi-Location Session
Best for couples who want multiple distinct backdrops, a wardrobe change, and the most variety in their final gallery.
- 2-hour extended cinematic session
- Multiple Chicago locations
- Wardrobe change welcome
- Naturally directed 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-star reviewed
Reach out anyway. Sunrise sessions, destination engagements, larger productions, and fully styled shoots can all be designed around your specific goals.
Have a vision that doesn't fit any of these?
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 two-location proposal session at $985 includes 75-90 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's the best value if you're planning both. Ask about this option when you reach out.
Questions About Pricing
What is included in every session?
Every session includes a personal planning consultation, location guidance, naturally directed 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. Every image edited individually, by hand. No batch processing.
How is each session designed?
Every session is custom-designed around the couple, the location, and the moment you're trying to create. The structures shown above are starting points. Anything can be refined to fit your specific vision. Reach out and we'll build something together.
Is there a discount for booking both a proposal and an engagement session?
Yes, in two ways. Our two-location proposal session at $985 includes 75-90 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.
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.
Jeremy is absolutely fantastic to work with; he IS incredibly positive and brings great energy to any event.
— KRISTINE M.
“
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.
22 Five-Star Google Reviews | 300+ Proposals Captured