Why Book an Engagement Session?

An engagement session gives you beautiful portraits for save-the-dates and announcements while building comfort with your photographer before the wedding.

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.

What Makes Our Engagement Sessions Different?

Natural direction means you'll feel like yourselves instead of mannequins. Every image hand-edited, never batch-processed or run through AI.

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 spent a decade working as an actor, acting coach, and director — including work at Steppenwolf Theatre Company and a Jeff Award for his craft. 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.

How Much Do Engagement Photos Cost in Chicago?

Engagement photography in Chicago ranges from $300 to $1,000+. Most couples invest $695 to $795 for a premium session with hand-edited delivery.

Pricing varies widely depending on the photographer's experience, editing quality, and session length. Budget sessions start around $300 to $500 but typically use preset filters and deliver smaller galleries. Premium engagement photography, like what we offer at The Proposal Studios, ranges from $695 to $795 and includes 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 Experience package, which combines both into a single session at a significant savings.

Engagement Photography Packages

Relaxed, cinematic sessions designed to capture your relationship as it really is. Every image hand-edited with intention.

The Portrait
$695
An unhurried 1.5-hour session at one or two Chicago locations. Enough time to settle in, explore, and walk away with images that feel effortless.
  • 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
Book Your Session
The Cinematic
$795
A full 2-hour session for couples who want to explore more of the city. Multiple locations, wardrobe changes, and a gallery with greater range and variety.
  • 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
Book Your Session

Enhancements

Rush delivery within 72 hours: $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
Tell Us About Yourselves
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.
Book Your Session

Best Places for Engagement Photos in Chicago

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.

North Avenue Beach
Skyline backdrop from the lakefront. Incredible at golden hour with the city behind you.
Lincoln Park
Tree-lined paths, the South Pond boardwalk, and the Nature Boardwalk with the skyline reflected in the water.
Chicago Riverwalk
Architecture, water, bridges, and golden light bouncing off the river. Urban and romantic.
Promontory Point
Dramatic lakefront views and historic stone architecture. Less crowded than the main beaches.
Olive Park
Quiet park just north of Navy Pier with some of the best skyline views in the city.
West Loop & Fulton Market
Industrial textures, murals, and modern architecture. Great for couples who want an urban edge.
Alfred Caldwell Lily Pool
A hidden gem in Lincoln Park. Lush, intimate, and almost impossibly peaceful.
North Shore Suburbs
Highland Park, Lake Forest, Evanston. Estates, gardens, and lakefront beauty north of the city.

We also photograph engagement sessions at sunrise for couples who want empty streets, soft light, and the city to themselves. Sunrise sessions are available as an add-on for any package.

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 theater background matters. We don't ask you to pose. We give you small, real prompts that bring out genuine reactions. Within five minutes, you'll forget the camera is there. That's when the best images happen.

How many photos will we receive?

The Portrait package delivers 50 to 70 hand-edited images. The Cinematic package delivers an extended gallery with greater variety across locations and looks. Every image is individually edited by hand, never batch-processed or run through AI software.

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 proposal Experience package ($895) includes a 60-75 minute cinematic portrait session after the proposal, which effectively replaces a separate engagement session. It's the best value if you're planning both. Ask us about the details during your inquiry.

Do you also photograph weddings?

Yes. The Proposal Studios is the sister brand of Jeremy Glickstein Photography, an award-winning Chicago wedding photography studio. Engagement clients receive an exclusive perk toward wedding photography. Same creative vision, same hand-edited care, from the engagement session 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.

Book Your Session
Wedding photography by Jeremy Glickstein Photography

Your Story Starts Here

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

A man in a beige coat celebrating with a woman in a black dress on a city bridge, popping champagne and holding glasses, during evening time.
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A smiling couple on the beach during sunset, holding each other and laughing.
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