Make Your Proposal Unforgettable – Iconic Locations & Stunning Photography


Navigating the journey to a perfect proposal in Chicago can feel overwhelming, whether you're a local or visiting the Windy City. Let us take the stress off your shoulders with expert planning, candid captures, and unparalleled attention to detail.


As Chicago’s leading proposal photography team, we specialize in turning ‘Will you marry me?’ into a breathtaking story you’ll cherish forever. With a commitment to seamless planning and stunning photography, we guarantee beautifully captured moments—whether it’s a secret setup or a candid, heartfelt reaction that you’ll relive for a lifetime.


As trusted Chicago proposal photographers, we know the city’s most stunning locations, including Millennium Park, Navy Pier, the Lincoln Park Zoo Bridge, and more. Whether you dream of proposing by the iconic Cloud Gate or a secluded romantic spot, we’ll guide you every step of the way.


Browse our portfolio of proposal photography in Chicago to see how we’ve helped couples create unforgettable memories. Don’t leave your special moment to chance—trust Chicago’s best proposal photographers to capture the magic.




Is a Proposal Photographer Worth It? Here’s Why You Should Hire One


Proposals have evolved from intimate moments into cherished milestones, often shared alongside engagement and wedding photos. Having a professional photographer capture this once-in-a-lifetime moment ensures every emotion, reaction, and detail is preserved beautifully.


According to The Knot's 2023 Real Weddings Study, 25% of proposers hired a professional photographer or additional vendors to assist with the proposal, more than double the rate in 2019. As social media continues to shape modern engagements, 58% of proposers report feeling pressure to plan highly unique proposals, often leading them to hire professional photographers to document and share these moments.


Beyond personal keepsakes, professional proposal photography enhances the engagement experience, ensuring picture-perfect memories in iconic Chicago locations. Whether you're a meticulous planner or orchestrating a last-minute surprise, hiring a Chicago proposal photographer guarantees a seamless experience and stunning images that tell your love story.


A couple in tan coats hold hands while walking together on an autumn day with blurred trees in the background.
Two people walk along a curved pathway near modern skyscrapers and autumn trees in an urban setting.
Two people share a moment under an umbrella on a rainy path surrounded by bare trees in a park.
A couple stands together by a waterfront railing with Chicago's iconic skyline and Lake Michigan in the background.
Close-up of hands showing an engagement ring with red nail polish and a sparkling diamond solitaire.
A happy couple in white clothing poses together outdoors with warm natural lighting and ornamental grasses in background.
A romantic proposal moment captured inside a lush greenhouse with tropical plants and glass ceiling.
A scenic view of tall buildings in a city park during autumn with bare trees and a person sitting on a bench.
A couple shares a special moment along Chicago's lakefront with the city skyline as a backdrop on a foggy day.
A romantic winter proposal scene at a park with Chicago's modern skyline and illuminated decorations in the background.
A couple shares a special moment in front of Chicago's iconic Cloud Gate sculpture, also known as The Bean, in Millennium Park.
People sitting on North Avenue Beach with the Chicago skyline visible in the background on a winter day.
A marriage proposal taking place in front of a large white Ferris wheel with a dome structure in the background.
Two people walking together in a sunlit greenhouse filled with lush plants and greenery.
A joyful proposal scene on a rooftop terrace with luxury apartments in the background.

Engagement Trends & Proposal Insights


📍 Annual Proposal Trends: Approximately 2.8 million couples get engaged annually in the U.S., though this number declined to 2.2 million in 2023. A rebound is expected, with projections of 2.4 to 2.5 million proposals in 2024 (Source: CNN).


📷 The Rise of Proposal Photography: Professional proposal photography is on the rise, with 25% of proposers hiring a photographer—a significant increase from previous years (Source: The Knot).


📅 Seasonal Proposal Trends: December remains the most popular month for engagements, accounting for 19% of proposals (Source: Statista).


📲 Social Media's Influence: With the rise of Instagram and TikTok, 58% of proposers feel pressured to create a highly unique and shareable proposal experience (Source: Houston Chronicle).

Capture the Moment, Create a Lasting Memory


Let us help you turn your proposal into a story you’ll relive forever. From scouting the perfect location to capturing the surprise, we ensure every detail is seamless. Book your Chicago proposal photography session today and make this magical moment unforgettable!

Ready to book?

Love & Celebration


30-minute  with a Professional Photographer

Private Online Gallery with All the Best Shots

15 Digital Photos beautifully Edited

Moments to Remember 

1-hour with a Professional Photographer

Private Online Gallery with All the Best Shots

30 Digital Photos beautifully Edited

Heartfelt Happenings

90-minutes with a Professional Photographer

Private Online Gallery with All the Best Shots

30 Digital Photos beautifully Edited


Curious About the Ideal Spot to Propose in Chicago?


Insights from The Knot suggest the most sought-after settings for proposals include vacations, meaningful personal spots, and iconic landmarks—a perfect blend of options offered by the Windy City.


Our expertise extends beyond just photography; we guide you in selecting the most picturesque location tailored to your unique story. Explore our curated list of Chicago’s Top 10 Proposal Spots or find inspiration from over 100 beautifully captured proposals in our gallery. From the stunning skyline at North Avenue Beach to the enchanting Chicago Riverwalk, we know each location's unique charm.


📍 Top Proposal Locations in Chicago:

  • North Avenue Beach – Stunning skyline views & romantic sunsets
  • Chicago Riverwalk – Iconic bridges & waterfront elegance
  • Millennium Park (Cloud Gate) – Classic, photogenic, and timeless
  • Lincoln Park Nature Boardwalk – Scenic city-meets-nature vibe
  • Wrigley Building & Michigan Ave – Perfect for city lovers
  • Olive Park - secluded city views
  • Alfred Caldwell Lily Pool - hidden garden-like spot in Lincoln Park
  • Rooftop bars & hotels - LondonHouse, The Robey, The Peninsula, etc.
  • Private Rooftop Venues – Intimate settings with breathtaking backdrops


🌦 Rain or Shine, Indoors or Outdoors: Our team is fully equipped to capture your proposal in any setting, ensuring your special moment is immortalized in the beauty and spirit of Chicago—no matter the season or weather.


Insights from The Knot suggest the most sought-after settings are vacations, meaningful personal spots, and iconic landmarks - a perfect blend of options offered by the Windy City.


Our expertise extends beyond just photography; we guide you in selecting the most picturesque location, tailored to your unique story. Explore our curated list of Chicago's Top 10 Proposal Spots or draw inspiration from over 100 beautifully captured proposals in our gallery. From the stunning skyline at North Avenue Beach to the enchanting Chicago Riverwalk and beyond, we know each location's unique charm. Rain or shine, indoors or outdoors, our team is equipped to capture your proposal in any setting - ensuring your special moment is immortalized in the beauty and spirit of Chicago, no matter the season or weatherRe

ady to plan the perfect proposal?