Chicago’s Most Artful Photography Experiences

Three ways to tell your story — each crafted with intention, discretion, and hand-edited, fine-art delivery.

Chicago proposal photographer capturing a skyline rooftop moment

Proposals

Marriage Proposal Photography

Discreet planning, precise timing, and cinematic coverage of the moment you ask. Delivery in days — never AI, never factory edits.

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Cinematic Chicago engagement session with champagne celebration

Engagements

Engagement Photography Sessions

Editorial polish with nostalgic warmth. Locations that fit your story; direction that feels natural — never stiff or cliché.

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Cinematic Chicago wedding photography by The Proposal Studios

Weddings

Wedding Photography & Film

Explore full-day collections and films with our sister brand — the same cinematic depth, emotion, and artistry.

Explore Weddings
Couple celebrating engagement with champagne on Chicago bridge at sunset
A couple stands close in an indoor greenhouse with large green plants and a glass ceiling, touching foreheads with eyes closed.
A couple stands on a bridge with a city skyline in the background, surrounded by red roses, candles, and a "MARRY ME" sign, during dusk.
A couple kissing on a bridge with a city skyline in the background.
A couple is embracing and smiling at each other on a rooftop at sunset with the city lights in the background. The woman is wearing a navy blazer dress and gold heels, and the man is in a beige blazer, plaid pants, and white sneakers.
A romantic proposal scene on a city bridge with a man smiling at a woman, a bouquet of red roses, and illuminated 'MARRY ME' sign, surrounded by scattered rose petals.
A man proposes marriage to a woman on a bridge with a city skyline in the background, decorated with roses, candles, and 'MARRY ME' letters.
A man and woman holding hands while walking on a beach at sunset.
A man proposing marriage to a woman on a bridge with a city skyline in the background. The man is kneeling with a ring, and the woman is smiling. Rose petals are scattered, and love signs are on the ground.
A man proposes marriage to a woman on a rooftop with a city skyline in the background. The man is kneeling with a ring, and the woman looks surprised and happy. There are rose petals scattered on the floor, a bouquet of roses, and a sign lit up that
A couple stands close together, embracing and touching foreheads in front of an orange metal structure with decorative panels, in an outdoor garden area with greenery and a cityscape in the background.
A man proposing to a woman on a glass observation deck high above a city at sunset, with city lights visible below.
A young couple holding hands by the waterfront with a city skyline and a crescent moon in the background at dusk.
A couple stands close together on a high-rise balcony overlooking a city skyline, with their foreheads touching, holding hands, and smiling, against a background of blue sky with clouds.
A man proposing marriage to a woman by a river with a city skyline in the background at sunset.
A couple holding hands and looking out a large window at a city skyline and water. The man wears a white shirt and blue pants, the woman wears a white and blue floral dress.
A couple sitting on the ground in front of a yellow wall with painted murals, including a heron, boats, trees, and a mailbox with graffiti, embracing and gazing at each other.
A couple kissing in front of a large window with a city skyline and water in the background.
A smiling woman and a man in a black suit standing near a waterfront at sunset, with city buildings in the background.
A man and woman stand outdoors with their backs against each other, eyes closed, as the woman gently rests her hand on the man's shoulder. They are surrounded by lush greenery and a tall tree with orange and green leaves, under a cloudy sky.
A couple stands together in front of a city skyline with skyscrapers, including the Willis Tower, under a cloudy sky, with a large dark industrial structure partially in frame on the left.
A man and woman standing outdoors under a cloudy sky, looking in different directions.
A man and woman holding hands stand in front of a large traditional Asian mural depicting trees, a crane, and a group of people on a hillside.
A couple celebrating by a body of water at night, with a city skyline and city lights in the background, holding a bottle of champagne and smiling.
A couple stands close together on a city sidewalk at sunset, with tall buildings in the background and warm orange light reflecting on the scene.
A woman and a man standing on a city bridge with tall buildings in the background in black and white.
A couple holding hands and walking in the shallow surf on a beach at sunset.
A couple lying on a bed surrounded by red and white rose petals, gazing into each other's eyes.
Black and white photo of a woman with light brown hair and a man with short hair and a beard, looking at each other outdoors against a cloudy sky.
Silhouette of a couple facing each other, standing close and smiling, against a glowing amber background in an indoor setting.
A man in a tan coat and a woman in a black dress celebrating on a bridge, with the man holding a champagne bottle and the woman holding a champagne flute, as they celebrate with champagne.
A man proposing marriage to a woman on a glass observation deck with a cityscape at sunset in the background.
A man and woman holding hands and kissing on a beach at sunset.
A man proposes to a woman in a desert landscape with tall palm trees and mountains in the background.

We’ve Captured Love Across Chicago… and the United States

From hidden skyline decks to serene parks and destination beaches, these moments reflect the heart of what we do—cinematic, personal, and undeniably real.

Skyline proposal at sunset from Willis Tower, 99th floor Chicago
Willis Tower • 99th Floor
Skyline proposal at sunset
Champagne celebration after a surprise proposal at Ping Tom Park, Chicago
Ping Tom Park
Champagne celebration by the river
Romantic proposal among the greenery at Garfield Park Conservatory
Garfield Park Conservatory
Proposal among lush greenery
Epic coastal proposal session at Stinson Beach, Marin County, California
Stinson Beach • Marin County, CA
Epic coastal proposal session

Why Choose The Proposal Studios

Because your proposal deserves more than a quick snapshot — it deserves storytelling, care, and the kind of artistry that stands the test of time.

Handcrafted Imagery

No AI filters. No auto batches. Every image is hand-edited for depth, tone, and timeless color — because this moment deserves intention.

Full-Service Experience

Planning help, location scouting, timing coordination — we make the entire process easy, discreet, and stress-free.

Cinematic Storytelling

Every session is approached like a short film — emotion, pacing, light, and narrative woven into one unforgettable visual story.

-Mikayla

“an absolute pleasure to work with and made us feel comfortable the whole time…if you're planning a surprise proposal and want every detail to be perfect, TPS is the one you need.”

What Our Clients Say

5-Star Google Business • Real words from couples whose proposals and engagements we've had the honor to capture.

"We couldn't be happier with our proposal and engagement photos. Jeremy captured us across Chicago — from Michigan Avenue to quiet corners along the Riverwalk — with such a cinematic eye. He somehow made two camera-shy people feel completely at ease. Our favorite image was taken near River Roast as the sun bounced off the bridge behind us. It feels like something out of a movie."

Nick & Kristine
Chicago Riverwalk

"Jeremy's been with us from our engagement to our wedding to family sessions — and every single shoot feels like art. He knows how to capture the real emotion and flow of a moment without ever making it feel posed. Every photo carries that same soulful, timeless energy."

Sean G.
Engagement Session

"Jeremy brings creativity and calm to every shoot. We loved how naturally the session unfolded — no stiff poses, just laughter, movement, and connection. The result was a blend of editorial elegance and nostalgic warmth that feels completely 'us.'"

Hanya S.
Editorial Engagement

"Jeremy helped me plan and photograph a surprise proposal at the beach — and made it effortless. He guided me through the setup, lighting, timing, everything. The photos are stunning — fine-art level, full of emotion. More than just pictures, they feel like a memory replayed beautifully."

Sebastian T.
North Avenue Beach Proposal

Frequently Asked Questions

How far in advance should I book my proposal session?

Ideally 3–6 weeks ahead to allow time for planning, permits, and location scouting. If you're working on a tighter timeline, reach out anyway — we often accommodate last-minute surprises.

Do you help plan the proposal or just photograph it?

We help with both. From scouting to timing to discreet positioning, we handle logistics so you can focus on the moment. Many clients describe us as their "covert creative partner."

Can we include friends or family after the proposal?

Absolutely. Whether it's a quiet champagne toast or a surprise reveal, we'll coordinate the timing to capture the emotion naturally and beautifully.

How soon will we see our photos?

You'll receive handcrafted highlights within 48 hours — perfect for social media. Full proposal galleries are delivered within 5-6 days, engagement sessions within 10 days. Every image is hand-edited for tone, mood, and artistry — never AI-processed or batch-edited.

Do you offer engagement or wedding photography too?

Yes — our sister brand, Jeremy Glickstein Photography, handles full wedding coverage with the same cinematic and intentional approach.

Can we choose specific Chicago locations?

Definitely. From Skydeck Chicago and Millennium Park to hidden lakeshore paths and Garfield Park Conservatory, we'll recommend ideal settings based on your vision, timing, and lighting.

Chicago proposal moment at North Avenue Beach Engagement session in Chicago city streets Cinematic wedding moment captured in Chicago

Ready to Plan Your Perfect Proposal?

Let's create something unforgettable together. Fill out the form below or call us at (312) 895-4560

Contact Us

Eager to explore a collaboration? Kindly share your details, and we will reach out to you promptly. We look forward to the opportunity to connect.