Chicago Engagement Photography
Why Book an Engagement Session?
Your wedding day moves fast. There's a timeline, a guest list, and a hundred things pulling your attention. An engagement session is the opposite of that. It's unhurried, unscripted, and entirely about the two of you.
It's also the smartest investment you can make for your wedding photography. By the time your wedding day arrives, you'll already know how we work together. You'll know what it feels like to be in front of the camera without feeling stiff. And you'll have a gallery of images that are genuinely yours, not poses from a Pinterest board.
Natural direction means you'll feel like yourselves instead of mannequins. Every image hand-edited individually.
Most engagement sessions feel awkward. A photographer points a camera at you and says "act natural" while you stand there wondering what to do with your hands. That's not how we work.
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. That background taught him something most photographers never learn: people look their best when they forget they're being watched. Instead of stiff poses and forced smiles, we give you small, real prompts that bring out genuine laughter, quiet intimacy, and the way you actually look at each other when no one else is around.
The result is images that feel like your relationship, not a stock photo of someone else's.
Engagement photography in Chicago ranges widely depending on experience, editing quality, and session
length. The Proposal Studios sessions run $750 to $850 and include extended sessions, multiple locations,
natural direction for genuine comfort, and a hand-edited gallery of 50 to 70 images delivered within 10 days.
If you're also booking proposal photography with us, ask about our two-location proposal session at $985. It combines both into a single experience at a meaningful savings.
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.
What Happens After You Reach Out
01. Share Your Vision
Fill out a quick inquiry or call us. Share your vibe, your favorite spots, and what you're hoping the session feels like. No wrong answers.
02. We Build Your Session
We'll suggest locations, timing, and wardrobe ideas based on your style and the look you're after. We'll plan everything so you just show up and enjoy it.
03. Relax and Be Yourselves
On the day, we handle everything. You'll forget the camera is there within five minutes. Your gallery is hand-edited and delivered within 10 days.
Chicago offers an incredible range of engagement session backdrops, from dramatic skyline views to quiet tree-lined paths and industrial urban texture.
We'll help you choose locations that match your style and the look you're after. Whether you want the classic Chicago skyline, a moody urban vibe, or something green and intimate, we know the spots that photograph beautifully at every time of day.
West Loop & Fulton Market
Industrial textures, murals, and modern architecture. Great for couples who want an urban edge.
Chicago Riverwalk
Architecture, water, bridges, and golden light bouncing off the river. Urban and romantic.
Alfred Caldwell Lily Pool
A hidden gem in Lincoln Park. Lush, intimate, and almost impossibly peaceful.
Lincoln Park & South Pond
Tree-lined paths, the South Pond boardwalk, and the Honeycomb Pavilion wit the skyline reflected in the water.
Promontory Point
Dramatic lakefront views and historic stone architecture. Less crowded than the main beaches.
North Avenue Beach
Skyline backdrop from the lakefront. Incredible at golden hour with the city behind you.
Skydeck Chicago at Willis Tower
103 stories above the city. A wow-factor backdrop for couples who want unforgettable.
Olive Park
Quiet park just north of Navy Pier with some of the best skyline views in the city.
Best Places for Engagement Photos in Chicago
Frequently Asked Questions
What should we wear to our engagement session?
Wear something that feels like you, not a costume. Solid colors and muted tones photograph beautifully. Avoid large logos or busy patterns. We'll share a style guide after you book and can offer recommendations based on your chosen locations and time of day.
When is the best time of day for engagement photos?
Golden hour (the hour before sunset) delivers the warmest, most cinematic light. Sunrise sessions offer similar quality with empty streets and a quieter feel. We'll recommend timing based on your locations and season.
We're awkward in front of cameras. Is that okay?
More than okay. Most of our couples say the same thing, and it's exactly why our background matters. 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.
How many photos will we receive?
The 1.5-hour session delivers 50 to 70 hand-edited images. The 2-hour session delivers an extended gallery with greater variety across locations and looks. Every image hand-edited individually.
How soon will we receive our gallery?
Full engagement galleries are delivered within 10 days. Rush delivery within 72 hours is available for $200. Your gallery includes full-resolution digital files ready for printing, social media, save-the-dates, and invitations.
Do we need a photography permit?
Some Chicago locations require permits for professional photography. We'll let you know during our planning call whether your chosen locations need one and point you in the right direction. No surprises on your session day.
Can we combine our proposal and engagement into one session?
Yes. Our two-location proposal session at $985 includes 75-90 minutes of cinematic portrait time across two Chicago locations with a wardrobe change welcome. Ideal for couples skipping a separate engagement session. Ask about this option when you reach out.
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.
Your Engagement Session Is Just the Beginning
The Proposal Studios is the sister brand of Jeremy Glickstein Photography. Engagement clients receive an exclusive credit toward wedding photography. By the time your wedding day arrives, we'll already know each other. You'll already be comfortable. And the images will reflect that from the first frame.
Ask about your wedding perk when you book your session.
Started
Get
Let's
Whether you have a vision in mind or just want to explore what's possible, we'd love to hear from you. Share a few details and we'll reach out personally, usually within a few hours. Or call us at (312) 895-4560
22 Five-Star Google Reviews | 300+ Proposals Captured