Hi, I'm Kenny Nakai.
As a Chicago wedding photographer, I’m lucky enough to document some of the city's most beautiful love stories.
I hope you find inspiration here and connect with the feelings I had when I created each photo.
Hi, I'm Kenny Nakai.
As a Chicago wedding photographer, I’m lucky enough to document some of the city's most beautiful love stories.
I hope you find inspiration here and connect with the feelings I had when I created each photo.
Because you can no longer imagine
life without them.
It's your moment. One that marks the beginning of everything that comes next. Let me help you plan it, protect it, and capture every expression so you can be fully present when it happens.
You've planned the ring.
You've planned the location.
Now comes the part
that keeps you up at night.
What if she finds out early?
What if the moment looks awkward?
What if I'm so nervous I can't even be present for it?
This is the most important question you've ever asked. You've been planning it for months. The last thing you need is to wonder whether the photos will do it justice. Or worse, whether anything will go wrong at all. That's exactly where I come in. I've photographed hundreds of Chicago proposals. I help you plan the moment, build the alibi, think through the light and the logistics. So when the time comes, your only job is to be there.
I know how the setting sun looks for your proposal at different locations along the lakefront. I know the rooftops with the best skyline angles and the quiet garden corners that feel more private. I know where the crowds might be in your background and give suggestions on how to deal with them.
But more than the locations — I know how to disappear. When the moment is happening, I'm already positioned. You won't feel me there. And that's exactly when the most real, most emotional photographs are made.
From your first message to the last photo delivered, I'm your guide. We'll talk through the plan together. I'll help you think through every variable: foot traffic, weather, timing, the cover story. You bring the love. I'll handle the rest.
THE PROCESS
How I make sure
everything goes
exactly right.
You don't need to have everything figured out when you reach out. Most people don't. That's what the first conversation is for. From location ideas to alibis to the exact angle I'll be standing. By the time the day arrives, you'll feel completely prepared. And so will I.
01
Planning the Moment
Every proposal starts with a conversation. You share your story, your vision, and what makes your relationship unique. I help you explore locations, timing, and overall feel: quiet and intimate, or iconic Chicago skyline backdrop.
We walk through every detail: foot traffic, lighting, weather, crowd patterns, the cover story. By the end of our first call, you'll have a plan that feels completely yours.
02
The Final Check-in
As the day approaches, we confirm every last detail. Any last-minute adjustments, questions, or new ideas are worked through together. This isn't just logistics. It's calm reassurance that everything has been considered.
You'll go into your proposal day feeling confident and prepared, not anxious. That calm shows up in your face and in the photos.
03
The Moment Itself
I arrive early. Always. I position myself so nothing looks forced or staged. When the moment unfolds, I'm already ready. Capturing every expression, every reaction, every tear, every laugh. You won't feel me there.
The result is genuine, beautifully composed imagery that honors both the significance of the moment and the energy of the city around you.
04
Same Day Delivery
I work fast. A handful of edited images are delivered the same night! So when you get back to your room, there's already something to look at together. Your full set of files arrives within a week.
You can share professional photos with family and friends before the night is even over. No waiting weeks to relive the moment.
"My fiance and I were absolutely delighted with the incredible work Kenny did in capturing our proposal! From my initial contact, he demonstrated great professionalism, clear communication, and enthusiasm for our special moment.
Kenny went above and beyond to ensure everything was perfect and helped us feel at ease before the big question was popped. He captured every raw emotion, genuine reaction, and the pure joy of the moment without us feeling intrusive."
SANDESH & NIKITHA
Every location. Every season.
Every kind of moment.
"Kenny is an excellent photographer. He helped me walk through my whole plan and was there for me every step of the way. He took every photo that I wanted and then some.
The quality of these photos were top tier. I cannot express how lucky I was to have Kenny there for my proposal. He directed us to take photos that I would not have thought of. He is a true professional!"
ESTHER & LUKE
What people say
after the moment is captured.
★★★★★
"I couldn't be happier with how our proposal photos turned out! Kenny captured everything so beautifully — from the emotions to the scenery, every shot was just perfect. His talent for finding the perfect angles is remarkable. The photos feel natural and full of emotion."
CRISTIAN & LIZETH
★★★★★
"Through the planning and implementation of the proposal I could tell Kenny had a lot of experience and helped consider different logistics such as people in the background and the wind conditions. He made us feel very comfortable and was able to get a lot of really amazing candid shots! This was one of the most important moments of my life and I'm glad Kenny was there to document it."
JOHNFAVOUR & MELANIE
★★★★★
Kenny was fantastic! I wanted my proposal to be a surprise and he helped me plan it out and even helped come up with an alibi. Not only were the pictures fantastic, his communication and expertise made the day perfect.
I HIGHLY RECOMMEND KENNY TO EVERYONE!! I couldn’t imagine having anyone else capture the moment, thanks Kenny!!
DON & LAURA
★★★★★
"The pictures came out AMAZING and are everything we could have hoped for. I'm so glad we trusted Kenny to capture this special moment and simply put would 100% recommend him for any event."
FAHAD & NASHWAH
★★★★★
"Very flexible with locations, and gave very good ideas to improve on my proposal. Kenny was amazing from beginning to end — will definitely recommend for a smooth process with great photos!"
LUCAS & BRUNA
★★★★★
"He was incredibly helpful in working with me to identify the right locations, talk logistics, and overall helped ensure everything was planned to perfection. Great guy, awesome photographer, and 100% a great decision to hire him."
STU & JESS
You don't need to have every detail figured out. Just send a message and we'll start talking through the plan together. Whether you're proposing in two weeks or six months, the earlier we connect, the more options we have.
Tell me what you're thinking: the location, the date, and any ideas you've had. I'll take it from there.
Chicago Proposal Photography · $600–$900
60–90 minutes · Weekday, weekend & holiday availability
Weather flexibility · Same-night image delivery
WHERE TO NEXT
SERVICES
Photos of couples before their wedding in different outfits and locations all over Chicago!
PORTFOLIO
Wedding Portfolio
See the work behind the words - real Chicago weddings photographed at the city's finest venues
HOME
Return to the homepage and learn more about working with me for your wedding day.
I'm Kenny Nakai, a Chicago proposal photographer creating beautifully planned, discreetly captured proposals since 2007. For partners who want the most important question of their life to look exactly as good as it feels.
