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 is a Jeff Award-winning actor with a credit at Steppenwolf Theatre Company, one of the most prestigious stages in the country, and brings over a decade of professional stage and screen experience to every session. 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 or more. Most couples invest $750 to $850 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 $750 to $850 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 two-location proposal session at $950, which combines both into a single experience at a meaningful savings.

Custom Engagement Sessions

Every session is designed around the couple, the locations, and the feeling you want to capture. The structures below are starting points. Anything can be refined to fit your specific vision.

$750
1.5-Hour Single-Location Session
An unhurried session at one or two Chicago locations. Enough time to settle in, explore, and walk away with images that feel effortless.
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
Book Your Session

Hand-edited · 10-day delivery · 5-star reviewed

$850
2-Hour Multi-Location Session
A full session for couples who want to explore more of the city. Multiple locations, wardrobe changes, and a gallery with greater range and variety.
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
Book Your Session

Hand-edited · 10-day delivery · 5-star reviewed

Have a vision that doesn't 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 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 & South Pond →
Tree-lined paths, the South Pond boardwalk, and the Honeycomb pavilion 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.
Skydeck Chicago at Willis Tower →
103 stories above the city. A wow-factor backdrop for couples who want unforgettable.

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 session.

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 credit at Steppenwolf Theatre Company, and that decade of stage and screen experience taught him how to direct people without making them feel directed. 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 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 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 two-location proposal session at $950 includes 75-90 minutes of cinematic portrait time across two Chicago locations with a wardrobe change welcome. It effectively replaces a separate engagement session and is the best value if you're planning both. 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.

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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Two men are holding hands, one standing and one sitting on a wooden bench inside a greenhouse with potted plants and trees around.
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A couple stands close together on a bridge, with a city skyline in the background. The woman is wearing a black dress, and the man is wearing a beige coat. They are holding each other tenderly, with romantic expressions. On the ground in front of the
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Two men joyfully embracing outdoors by the water, smiling with eyes closed, one giving a piggyback ride.
Two men standing outdoors in a natural setting, one in the foreground and the other in the background, both smiling and wearing casual shirts.
Two men with beards and short hair leaning noses to each other in a loving pose outdoors, with blurred natural background and sunlight.
Two men lying on a blanket in a grassy park, one with his arm around the other, both wearing patterned shirts and jeans, enjoying a peaceful moment.
Two men with beards and sunglasses sitting close together outdoors, with their heads touching.
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Two men sitting on a purple velvet couch in a bright room, smiling and talking, with drinks on a glass table in front of them.
Two men are sitting at a bar, facing each other, engaging in conversation. One man is holding a tie, and the other has his hand on the other's knee. The bar is stocked with bottles in the background.
Two men in business attire sharing a happy moment at a restaurant table, smiling and leaning close together.
A couple holding hands, walking on the wet sand at the beach during sunset.
A smiling couple on the beach during sunset, holding each other and laughing.
Silhouetted couple holding hands on a beach at sunset or sunrise.
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Two people standing on a wooden bridge over a body of water, surrounded by trees and greenery.
A couple sharing a happy moment at night by the water with a city skyline and illuminated buildings in the background.
A woman is spraying champagne at a man on a waterfront with the city skyline in the background during nighttime.
A man and woman celebrating with a bottle of champagne at night with a city skyline in the background, rain falling.
A man and woman standing close together outdoors with their eyes closed, enjoying a peaceful moment. The woman rests her hand on the man's shoulder, and they are surrounded by trees with autumn-colored leaves under a cloudy sky.
A woman and a man standing on a city bridge with tall buildings in the background, in black and white.
A couple is standing close to each other on a city sidewalk during sunset, near a river with modern skyscrapers in the background.
A woman with dark hair in a white blouse and black cardigan stands behind a man with a beard in a gray sweater, sitting in a leather armchair in a wood-paneled room with a chandelier overhead.
A couple sitting in a cozy wooden booth in a restaurant, leaning close and gazing into each other's eyes, with warm lighting and framed artwork on the wall behind them.
A woman sitting on a bar counter touching the nose of a man standing in front of her in a dimly lit bar with wooden decor.
A man and a woman stand outdoors under a cloudy sky, looking in different directions.
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A man and woman holding hands and looking at each other in front of a large mural featuring trees, flowers, and people in traditional clothing.
A couple walking hand in hand on a city sidewalk, smiling, with a building and trees in the background.
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A young couple sits on the ground in front of a yellow brick wall with colorful mural art, including a heron, red flowers, a boat, and a cloudscape, sharing an intimate moment.
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A smiling couple standing outdoors in front of the Chicago skyline, including the Willis Tower, under a cloudy sky.
A black and white photo of a man and woman standing outdoors near a river, with a city building and cloudy sky in the background. The woman stands behind the man with her hands resting on his shoulders.