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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.

CHICAGO ENGAGEMENT PHOTOGRAPHY

Engagement photos
that feel natural

yet take your
breath away.

You should look amazing. You should feel completely like yourselves. Both things are possible. I've spent 19 years figuring out how to make them happen at the same time.

BASED IN CHICAGO · AVAILABLE WORLDWIDE

19 YEARS PHOTOGRAPHING CHICAGO COUPLES

What most couples feel before their session

You want to look good.
You don't want to look

like you're trying to look good.

"We're not really photogenic people." "We don't know how to pose."

"What if it feels awkward and forced?"

I often hear some version of this from couples before their session. And after 10 to 15 minutes, they nearly always says the same thing: "Oh...this is actually fun." That shift is the job. Not just capturing beautiful images, but creating the space where you forget the camera is there. That's where the real photos happen. And that's what I've built my entire process around.

How I Work with You

Most couples have never been professionally photographed before. That's where I come in.

Chicago engagement photography is more than choosing a beautiful backdrop. It's about creating images that feel natural, authentic, and unmistakably you. My priority is simple: you should look and feel your best.

I approach every session with calm direction and an editorial eye... guiding you through natural movements and flattering poses that never feel stiff or forced. We all have flattering and unflattering angles. My job is to find yours.

I give you space. Sometimes I'll send you walking 50 feet ahead of me so you can exhale and just be together while I work. I hold back when a real moment is unfolding. I step in when you need direction. By the end of the session, most couples tell me they feel comfortable posing and flowing through photos on their wedding day.

FEEL YOURSELF

"Such an amazing photographer! It was our first time taking professional photos as a couple and he captured every moment so beautifully and made us feel comfortable the entire time! So impressed with how the photos turned out!"

PUJA & KISHAN

What Every Session Includes

What 19 years of Chicago engagement photography

actually gives you.

An engagement session isn't just about getting beautiful photos, though you will. It's about learning how to be in front of my camera before your wedding day. It builds trust. It dissolves nerves. And it produces images you'll share for years. Here's exactly what goes into making that happen.

01

Location guidance that fits you, not the trend

I start every conversation the same way: "Are there any locations that have sentimental value to you? Any vibes you have in mind?" We start there, then I bring in my knowledge of what works best at different times of day, seasons, and light conditions. I have an extensive library of Chicago locations. From the iconic to the unexpected, and I match them to your vision, not just what looks good on my website.

02

Calm direction from someone who's seen everything

You don't need to know how to pose. That's my job. I direct with confidence but never make it feel like a production. I watch for the light, the angles, and the expressions. I give you clear, natural direction that helps you look your best without feeling like you're performing. Most couples are surprised by how quickly it starts to feel comfortable.

03

Chicago in every season. I know this city

I know exactly which trees in Lincoln Park peak first in October and which ones hold their color into November. I know where the light breaks between the buildings on LaSalle Street Avenue in September. I know the paths along the Riverwalk that feel like a movie set at night. Your session isn't just in Chicago. It should feel Chicago.

04

Multiple locations and outfits, 90–120 minutes

Engagement sessions can range from 90 to 120 minutes with up to three locations and three outfits. This gives us the flexibility to capture a range of vibes. More relaxed and romantic in one spot, more editorial and architectural in another. We're never in a rush. I work fast through poses and transitions so we maximize the time without it ever feeling overwhelming.

05

Personal editing on every image. By me

Every photograph from your engagement session is personally edited by me. Consistent color, light, and tone. Timeless in feel. A curated selection of your favorites is also hand-retouched. Distracting background elements or anything that pulls your attention away from the two of you. The goal is polished, natural, and effortless. Nothing that looks worked on.

06

Your rehearsal for the wedding day

This is the one that most couples don't realize until after. By the time your wedding day arrives, you've already learned my cues. You know how I work, and I know how you move. That familiarity means you can relax on the most important day of your life: knowing you will look good in your photos...instead of spending the first hour of portraits figure out my directions.

IN THEIR OWN WORDS

"He cares deeply about taking beautiful, timeless and modern photojournalistic style photos.

He goes above and beyond what you expect. The photos were absolutely spectacular and technically gorgeous. Kenny gives you careful, attentive personalized service that is second to none."

JEANAH & BRIAN

CHICAGO ENGAGEMENT LOCATIONS

Iconic locations.

Unexpected corners.

Every kind of light.

Chicago offers an extraordinary range of settings: from iconic skyline views, the Riverwalk, Buckingham Fountain, Millennium Park, and historic bridges to quieter natural spaces, urban art in Wicker Park, and the industrial vibe of the West Loop. Each location is chosen to reflect your style. Sometimes the setting is instantly recognizable. Sometimes it's something unexpected. We work together to match your vibe and vision.

ENGAGEMENT PHOTOGRAPHER REVIEW

"We hired Kenny for a photoshoot and couldn't be happier with the results! Not only did we have a great time during the session, but Kenny was incredibly professional, flexible, and responsive throughout the entire process. He answered all our questions promptly and thoroughly. We came in with a few ideas, and he brought them to life with his creative eye and deep knowledge of great photo spots around the city. He guided us through a variety of poses and helped us feel completely comfortable in front of the camera."

YERI & MARK

OPTIONAL NIGHT SESSION

Chicago at night.

A completely different city.

I love how Chicago comes alive after dark. Everything looks different. A little more romantic. A little more dramatic. A little more cinematic.

 

Taking photos at night is much more technically demanding. The light, the exposure, and the way the city looks changes completely. It requires a different kind of confidence in front of the camera, which is why I offer it as an add-on to a daytime session. You learn how to be directed in the daylight first and then when we step into the city at night, the results are spectacular.

 

The Chicago Riverwalk after dark. State Street with the lights from the Chicago Theatre. Michigan Avenue bridges at midnight. If you're open to it, a night session produces some of the most memorable images of the whole engagement experience.

ENGAGEMENT PHOTOGRAPHER FAQs

Everything you're wondering about your engagement session.

Answered honestly — because you deserve to know exactly what you're getting into before you say yes.

Most couples have never been professionally photographed before and your wedding day is not the ideal time to figure out your best angles and how to follow a photographer's cues and directions. For most, it takes time to feel comfortable in front of a camera.

An engagement session helps with that.

You get beautiful, professional, authentic photos of this season of your relationship. And on your wedding day, it makes my job as your Chicago wedding photographer easier. You already know my cues, you've built trust, and you know the photos will look good. It makes the portrait time on your wedding day so much more relaxed and enjoyable. Not required — but I always recommend it.

I always start with the same question: "Are there any locations that have sentimental value to you, or any vibes you have in mind?"

We start there, then I bring in my knowledge of what works best for your style, the time of day, and the season.

A typical daytime engagement session is 90 minutes with up to two locations and two outfits. I have an extensive library of hand-selected Chicago locations and I'm happy to share ideas once we start talking.

I also offer a night session as an add-on where we pick a location that looks amazing once the sun goes down.

Of course...that's what I do.

We all have flattering and unflattering angles, and most people genuinely don't know theirs until someone shows them.

During your session we work together to find the poses that look the best and feel the most natural. I give clear direction without making it feel like a production. About 10 to 15 minutes in, someone often says "oh, this is actually fun." By then we're usually just getting started.

Yes, and I love how Chicago looks at night. Everything is a little more romantic, a little more dramatic. But taking photos at night is much more technically demanding from a photography standpoint, so I only offer it as an add-on to a daytime session. You have to learn how to be directed and flow through poses during the day so that when we step into the city at night, everything goes smoothly. The results are worth it.

Every image is personally edited by me for consistent color, light, and tone. A curated selection of your favorites is also hand-retouched with distracting elements removed. Anything that pulls attention away from the two of you.

I don't outsource editing. I don't batch-process. Every photo you receive has been seen by me, selected by me, and edited by me. That's what takes the time and that's what makes the difference.

Chicago engagement sessions typically range from $800–$1,650, depending on the scope of the session.

That includes 90–120 minutes, up to two locations and outfits, weekday and weekend availability, an optional night session add-on, and all the Nakai Essentials. Head to the info and pricing page for full details, or just reach out and we can talk through what makes sense for you.

BOOK YOUR SESSION

Let's talk about your engagement photography.

Tell me about your vision: any locations you've been thinking about, what kind of feel you're going for, or even just that you have no idea yet. That's what the first conversation is for.

 

Every engagement session is different because every couple is different. I'd love to hear your story.

"He goes above and beyond to capture the best possible shots. We cannot recommend him enough!"
-Amalia & Stephen

90–120 min · Up to three locations + outfits
Weekday & weekend · Optional night session

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I'm Kenny Nakai, a Chicago engagement photographer creating relaxed, story-driven engagement sessions since 2007. For couples who want to remember how it felt when it all began.

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