07/01/2025
As a Chicago proposal photographer, engagement season holds a special place in my heart. This magical time of year brings an influx of couples seeking to capture one of the most important moments of their lives: their marriage proposal. From the excitement of preparing the perfect plan to the thrill of seeing the joy on your partner's face when they exclaim "Yes!", there's no greater honor than helping document such a personal and unforgettable experience.
💍 What is Engagement Season?
In the world of marriage proposals, engagement season is a magical period when most couples decide to pop the question. For photographers, it's the time when social media feeds are filled with engagement announcements and glowing couples sharing their big news. Engagement season typically spans from late fall to early winter, with the peak happening between November and February.
The numbers don't lie — according to The Knot's Real Weddings Study, nearly 45% of couples get engaged during this time.
💍 Planning the Perfect Proposal: A Photographer’s Perspective
The excitement of a proposal is contagious, and every couples' journey to this moment is unique. As a photographer, my job is to help capture these once-in-a-lifetime memories. But before the ring is even on the table, there’s a lot of planning involved. Proposals are deeply personal moments that reflect the couple’s shared interests, personalities, and dreams. For instance, if your partner loves the outdoors, imagine popping the question during a winter walk along the Chicago Riverwalk or a cozy winter stroll in Lincoln Park's South Pond Boardwalk. Not into the outdoors? We've also got some great indoor options which offer climate-controlled environments and absolute privacy such as proposing at The Rookery in Downtown Chicago. When the moment is as personal and thoughtful as the relationship itself, it’s guaranteed to be extraordinary!
A key part of proposal planning is knowing whether or not you’d like professional help. A growing trend has been for proposers to hire photographers like Jason Kaczorowski Photography to document the big moment. The Knot's Jewelry & Engagement Study found that a growing number of couples hire a photographer to capture the proposal. As a Chicago-based proposal photographer, I’ve had the honor of witnessing proposals in stunning Chicago locations — sometimes right under the city’s iconic skyline, at a private stunning indoor location, or even during an intimate rooftop. Professional photographers not only ensure that the moment is beautifully captured but also take the pressure off you, letting you focus on the excitement of your big question.
💍 Ring Shopping: Should They Be Involved?
Another major part of preparing for the proposal is the engagement ring. In today’s world, many couples choose to shop for the ring together or, at the very least, discuss what type of ring they’d love. Research shows that 77% of people had a hand in choosing their engagement ring. In fact, 29% of couples intentionally picked out the ring together before the proposal, which helps avoid any surprises but, of course, in the best way possible! If you’re unsure whether your partner wants to be involved in the process, it’s always a good idea to ask them early on. This way, you can keep them on their toes while still being confident in your choice of a meaningful and personal ring.
💍 Crafting the Perfect Proposal: What to Say?
Now, let’s talk about the heart of the proposal itself and specifically, what you’ll say when the moment arrives.
While many choose the classic, "Will you marry me?", some couples prefer a more personalized speech that truly reflects their relationship. Whether you’re going for something sentimental or lighthearted, the key is to speak from the heart. As someone who captures these moments, I can tell you that it’s not about perfection—it’s about raw emotion. Practice your words beforehand, but don't worry about the nerves. It’s perfectly normal to feel jittery at such a pivotal moment.
💍 Proposal Trends in 2025: What to Expect
As a photographer, I’ve noticed a few key trends emerging in the proposal scene:
Personalization is Key: Gone are the days of generic proposals. Today’s couples are focused on creating unique experiences that reflect their love story. Whether it’s using an heirloom ring or incorporating a favorite movie or hobby, making the proposal your own has become more important than ever.
Higher Investment in the Proposal: Proposals have evolved into significant events, with couples investing more in the experience itself. On average, proposers are spending over $2,500 on the proposal (excluding the ring), creating memorable and shareable experiences that are just as important as the wedding day itself.
Social Media and Proposals: Platforms like Instagram and Facebook have become integral to the proposal process, offering inspiration and becoming the space where couples share their big news. In fact, nearly 75% of couples announce their engagement on social media within two days of the proposal.
📸 We’ve had the privilege of photographing more than 750 proposals in Chicago and throughout the world from intimate, quiet moments to grand, spectacular events. No matter how it’s planned, the proposal is a magical experience, and being able to preserve those memories through photography is something I deeply cherish. If you’re planning your proposal this engagement season, take the time to make it personal, memorable, and most importantly, true to the love you share with your partner. And don’t forget—whether you go big or keep it intimate, capturing those first moments of joy is priceless.
Our team will handle everything from location ideas to securing permits (if needed) and even arriving early to ensure the perfect moment. We offer different styles of capturing your proposal – whether you're into candid shots or want a more hands-on approach! Plus, you’ll get your photos SAME DAY!
And here's the BEST part: We're so confident you'll love working with us that your "Yes!" moment is FREE! We'll rebate your Proposal Photography cost and apply it toward your Wedding Photography if you choose us for your big day too!
Contact Us TODAY to start planning your perfect Chicago proposal.
Chicago Wedding & Portrait Photographer, Jason Kaczorowski Photography
