A man is proposing marriage to a woman in a high-rise building with a city view in the background. The man is on one knee, holding out a ring box, while the woman responds with surprise and happiness.

Chicago’s Most Cinematic, Custom

Proposal Photography Experience

We don’t just capture the moment—you live it.

Every proposal is artfully planned,

creatively directed, and soulfully

photographed with emotion, intention, and style.

For couples who want more than a quick gallery—

they want a memory that moves.

Google logo with five yellow stars below it on a black background.

Proposal & Engagement Photography That’s

Personal, Powerful, and Unforgettable

Each couple’s story is different—and your photos should be, too. Below are real images from surprise proposals and engagement sessions we’ve captured throughout Chicago, from hidden rooftop moments to golden-hour strolls through Lincoln Park. Whether you're planning a cinematic surprise or celebrating your love with an intimate portrait session, these images show what’s possible when creativity, intention, and emotion come together.

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.

-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.”

-Sophia + Michael

“ THE Best Artistic PHOTOGRAPHERS AROUND.”

-TESTIMONIALS-

chicago’s premier proposal Photographers

A man kneeling on one knee on a glass floor, holding a small box and proposing to a woman on a high rooftop with a city skyline at sunset in the background. The woman is smiling and wearing a navy blazer and gold high heels.

MARRIAGE PROPOSAL PHOTOGRAPHY SESSIONS

STARTING at 695 | MOST POPULAR 875

Indulge in exquisite artistry with our Galleria Prints, where each photograph is transformed into a stunning masterpiece. Our premium print services capture every detail, offering you the ultimate expression of elegance and sophistication.

A man and woman standing close together on a park bench in front of a traditional pavilion with a tiled roof, surrounded by lush greenery with tall trees and a high-rise apartment building in the background.

ENGAGMENT PHOTOGRAPHY SESSIONS

STARTING at 750 | MOST POPULAR 875

Dive into a curated collection where artistry meets luxury. Our gallery transcends mere visuals, providing a sophisticated haven for discerning connoisseurs of fine photography.

A happy bride and groom in wedding attire sharing a moment outdoors, surrounded by trees.

WEDDING PHOTOGRAPHY & FILM COLLECTIONS

4.5K to 10.5K DEPENDING ON CUSTOMIZATION. AVG 6K

Craft the perfect showcase for your memories with our bespoke framing service. Each piece is afforded unmatched attention and designed to enhance your space with timeless sophistication. Visit our sister company to learn more: WEDDING PHOTO & FILM COLLECTIONS

Our company ethos

e·thos

/ˈēˌTHäs/

noun

  1. the characteristic spirit of a culture, era, or community as manifested in its beliefs and aspirations.

At The Proposal Studios, we believe in celebrating love stories with artistry, intention, and heart. We approach every proposal session as an opportunity to create something extraordinary—not just capturing a moment but telling the story of your journey together.

Our ethos is rooted in personalization and creativity. Each session is tailored to reflect your unique connection, whether it’s incorporating personal elements like a championship belt for a boxing enthusiast or designing a shoot that aligns with your passions and personalities.

We embrace a blend of timeless elegance and modern artistry, avoiding clichéd poses or over-editing in favor of images that feel natural, emotional, and authentic. Our goal is to provide not just photography but a bespoke experience that elevates your proposal into a memory that will last forever.

With a deep respect for the importance of this milestone, we are committed to delivering a service that combines professionalism, creativity, and care. Your love story is exceptional—and it deserves to be captured with the same level of distinction.

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.