Chicago Engagement Photography

Chicago Engagement Photography

Cinematic portraits for couples
who do things their own way.

Comfort-first direction. Zero stiff posing. Photos that feel like you.

Sessions from $750 | Most couples invest $850–$1,050

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48–72 Hour Highlights · Camera-Shy Friendly · 151+ Five-Star Reviews

For Couples Who Want Artful Portraits, Not Templates

Cinematic portraits — guided by an artist, never forced. Real connection, bold Chicago scenes, your vibe.

With roots as an actor and director, I bring comfort-first direction and natural pacing that help even camera-shy couples relax into the moment. Every session is crafted to feel spontaneous, stylish, and authentically you.

"Jeremy made the entire process incredibly comfortable for us. His professionalism, kindness, and exceptional skill set him apart. He has a true gift for putting clients at ease and capturing genuine, heartfelt moments." — Nick & Kristine · Riverwalk Engagement
107 ★★★★★ on Google Multicultural & LGBTQ+ Camera-shy Friendly

★ Read 100+ Five-Star Google Reviews

Engagement Session Collections

Outcome-first, never cookie-cutter—planned by light & location with comfort-first direction. Highlights in 48–72 hours.

Most Popular

Cinematic Session

$825 • ~2 hours • 2 locations

  • Storyboarded locations + timing by light
  • Guided prompts, zero stiff posing
  • ~90–120 edited images
Book Cinematic

Signature

$750 • ~1.5 hours • 1–2 locations

  • Planned route + golden hour
  • Comfort-first direction
  • ~60–100 edited images
Book Signature

Sunrise Add-On

$295 • optional

  • Low-crowd, luminous light
  • Lakefront skyline options
  • Pairs with any session
Add Sunrise

Rush Delivery

$295 • optional

  • Priority curation + edit
  • 72-hour gallery delivery
  • Great for tight timelines
Add Rush
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Engagement Sessions — Quick Answers

How do we choose locations?

Start with meaning—first date, neighborhood, skyline views—then I layer light and scenery for variety.

What should we wear?

Complementary tones, movement-friendly fabrics, one elevated look. I'll send a quick style guide.

Can we bring our dog?

Yes! Bring a handler; we'll plan a pet-friendly stop and a clean background.

How long is the session?

Typically 60–90 minutes across 1–2 locations, timed for the best light.

Do you travel outside Chicago?

Yes—suburbs and destinations with simple travel add-ons.

Why do an engagement session?

Celebrate your story, get camera-comfortable, and create art for save-the-dates or displays.

Check Availability See Packages Read 100+ Google Reviews
A couple stands outdoors with their eyes closed, embracing each other against a background of trees with autumn leaves and dark cloudy skies.
Couple with foreheads touching, eyes closed, smiling gently outdoors with city buildings and river in the background.
A man and a woman standing outdoors under cloudy skies, looking away in contemplative poses.
Two people holding hands in front of a large traditional Asian mural with trees, flowers, and people, during nighttime.
A black and white photo of a man and woman standing outdoors near a river, with an urban building and cloudy sky in the background. The woman stands behind the man, resting her hands on his shoulders.
A couple smiling and embracing in front of a blue brick wall, with green leaves at the top of the image.
A couple standing close together in front of a large brick building with arched windows, holding hands and looking at each other.
A couple standing close together outdoors in front of a city skyline with tall buildings and a cloudy sky, near a large, tilted metal structure.
A couple holding hands walking along a beach at sunset.
Two young people blowing confetti in a subway or train station.
Two men with sunglasses leaning their heads together on a sunny day
A smiling woman in a black jacket standing by a waterfront at sunset with a man partly behind her, with tall city buildings in the background.
A couple standing close and looking at each other by Lake Michigan during sunset with the Chicago skyline in the background.
A man and a woman standing face-to-face in front of a gold-colored metal grid or fence, with the woman having braids and the man wearing a black t-shirt, in a well-lit indoor setting.
Two men lying on a striped blanket on green grass, one resting his hand on the other's chest, enjoying a sunny day outdoors.
A smiling couple embracing outdoors at sunset, framed by a large neon heart sign.
Two men holding hands, standing outdoors with trees and a clear sky in the background, wearing patterned shirts and sunglasses.
A couple embracing in front of a white brick wall covered with green and red ivy leaves.
Two men walking arm in arm on a path outdoors, smiling and close to each other, with trees in the background.
A man and woman leaning against a brick corner wall, with blue and yellow paint behind them. The man is wearing glasses, a pink blazer, white shirt, and dark pants, with one hand in his pocket. The woman is wearing a red dress with a white pattern, h
A couple sitting closely on a patterned couch, touching forehead to forehead, with their eyes closed and hands clasped, in a cozy living room decorated with framed artwork and colorful pillows.
A couple sitting on a park bench, smiling and embracing each other, outdoors.
Two people holding photo masks over their faces, one with a black-and-white photo of a smiling man with a beard, and the other with an album cover of Lady Gaga and Joanne in profile, inside a room with shelves, artwork, and a decorative animal skull.
A couple with their foreheads and noses touching, holding each other close in a living room with a gallery wall of various colorful art and posters behind them.
A couple sitting on a park bench, leaning close to each other and holding hands, surrounded by greenery.
A man and woman holding hands, standing in front of a wall mural of black and colored floral designs.
Two men conversing outdoors during sunset, one man with hand on his head appears thoughtful, the other is blurry in the foreground. Sunlight creates a warm glow.
A young woman with black hair and a young man with brown hair sit on a park bench back-to-back, smiling. The woman wears a white shirt and black ripped jeans, while the man wears a blue shirt and dark pants. Autumn trees with orange and yellow leaves
Two men smiling and embracing each other near a body of water, with one giving a piggyback ride to the other, outdoors with grass and a sandy area.
A young couple standing close to each other with foreheads touching, eyes closed, and smiling slightly, against a pink-lit concrete wall.
Two men with beards, one lying on the ground and the other leaning over him, smiling at each other outdoors on a grassy field.
A couple is standing close together, touching foreheads and smiling, against a large white brick wall during sunset.
A young woman with blonde braids wearing a black off-shoulder top and ripped denim shorts stands with her hands in her pockets, looking down. Behind her, a young man in a black t-shirt and camouflage shorts is leaning against a beige wall, looking at
Two men holding hands and walking away in an outdoor setting, with their shadows cast on the ground. One is wearing dark pants, and the other is in light-colored pants, both in short-sleeved shirts.
A young couple sitting on metal stairs, smiling and leaning close to each other, face to face, in an urban setting.
Two men lying on a blanket in a grassy park, smiling at each other.
A young man and woman standing back-to-back against a reflective black tiled wall in an urban downtown area. The man is wearing a black T-shirt and camouflage pants, with one foot raised and leaning against the wall. The woman is wearing a black off-
Two men with beards and short hair embracing outdoors with foreheads touching and eyes closed, smiling, during sunset.
Two men with beards smiling and with foreheads touching, standing outdoors at sunset.
Two men holding hands and walking along a sandy path at sunset, smiling, with trees in the background.
Two men standing outdoors in a field with trees in the background, one in the foreground looking to the left and the other in the background smiling and looking at the first man, both wearing casual shirts.
Two men with beards hugging and touching foreheads, sitting on a blanket in a park on a sunny day, smiling with eyes closed.
Two men, smiling, sitting close on a purple couch, engaging in a warm moment of affection. One man is wearing a light-colored blazer and the other a dark blazer. They are in a room with elegant white cabinetry and a fireplace in the background.
Two men sitting on a purple velvet sofa in a well-decorated room, smiling and engaging in conversation, with drinks on a glass table in front of them.
A man and woman stand close together in a narrow brick hallway. The woman, smiling and fittingly affectionate, has her arm around the man's shoulder. The man looks away with a neutral expression. The hallway is warmly lit at the ceiling.
Two men in business casual attire holding hands and standing against a dark brown wall, looking at each other, smiling.
Two men are sitting at a restaurant table, smiling and laughing together. One man is adjusting his tie while the other is facing him. There are drinks and rolled napkins on the table, and a tufted headboard-like booth backdrop behind them.
Two men standing outdoors on a waterfront, holding hands behind their backs, with city buildings in the background.
Two men walk along a pier beside a large body of water with a city skyline in the background on a sunny day.
A couple sharing a kiss on the beach at sunset, holding hands, with the ocean and colorful sky in the background.
A couple standing close together in front of a wooden door near a window, smiling and enjoying each other's company in sunlight.
A couple laughing and embracing on a beach at sunset, with the ocean and a colorful sky in the background.
A couple laughing and playing on the beach at sunset, with the man holding the woman in his arms as she leans back, both smiling joyfully.
A black and white photo of a couple embracing on the beach at sunset, with the woman being lifted off the ground, both barefoot, with waves in the background.
A couple hugging on the beach during sunset with ocean in the background.
A couple holding hands standing in the shallow water at the beach during sunset
Silhouette of a couple holding hands on the beach at sunset, facing the ocean.
A man proposing to a woman on a waterfront with a city skyline in the background during sunset.
Close-up of a couple embracing, with the woman resting her head on the man's shoulder or chest, and the man looking content with a slight smile, wearing a light-colored shirt.
Two people standing near a city street during sunset, looking away from the camera.
A man and woman embrace closely with their eyes closed against a concrete wall, conveying intimacy and connection.
A couple sharing a kiss by the water with a city skyline in the background at sunset.
A man and a woman are standing side by side against a textured concrete wall, holding hands. The woman has natural curly hair and is wearing a black spaghetti strap top and light blue jeans. The man has short hair and is wearing a beige button-up shi
A man and woman dancing on a beach at sunset, with the ocean and a partly cloudy sky in the background.
A man and woman on a seaside promenade during sunset. The man is dipping the woman backwards in a dance move.
A couple holding hands and smiling while walking along the shoreline of a city waterfront at sunset, with a city skyline and half moon in the sky.
A couple walking hand-in-hand along a pathway near the beach, smiling and talking, with trees and streetlights in the background during dusk.
A couple embracing and smiling in front of a white door in a black wall, with minimal surroundings.
A large mural of a geometrical giraffe and a stylized white deer with antlers touching noses, set against a night landscape with mountains, water, and a starry sky. Two people stand in front of the mural, embracing.
A couple shares an intimate moment with their foreheads touching and eyes closed against a blue textured wall.

Let's Start Your Cinematic Session

Painterly light, true color, and natural direction—crafted around your story.

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The Full Story

Your engagement is just the beginning

Wedding Photography

Most engagement clients continue with me for their wedding. Same style, same comfort, deeper connection.

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Proposal Photography

Know someone about to pop the question? Discreet coverage that captures every genuine emotion.

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Chicago Winery Weddings

Still choosing a venue? I'm a preferred vendor here—happy to share what makes it special.

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Investment & Pricing

Transparent pricing for all services. No surprises, no hidden fees.

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151+ Five-Star Reviews

See what couples say—especially those who felt camera-shy before we worked together.

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Questions & Answers

What to wear, best locations, timing by light, and everything else you're wondering.

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