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Nakai Photography Logo White

 

CHICAGO ENGAGEMENT PHOTOGRAPHY

Engagement Photos That Feel Natural

Yet Take Your Breath Away

Chicago engagement photography is more than choosing a beautiful backdrop—it’s about creating images that feel elevated, authentic, and unmistakably you. With over 19 years of experience, I guide couples through every part of the process, from selecting the perfect location to feeling confident and comfortable in front of the camera.

My priority is simple: you should look and feel your best. Engagement sessions are a celebration of this chapter in your relationship, and I approach them with the same care and attention as your wedding day. Through calm direction and an editorial eye, I guide you through natural movements and flattering poses — never stiff and never forced.

sunflare between smiling faces chicago sunset engagement photo
chicago botanic garden engagement photos sunset
engagement photos chicago romantic puppy rooftop

"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

Iconic Locations for Chicago Engagement Photography

Chicago offers an extraordinary range of settings and I approach each engagement session with intention. From iconic skyline views, the Riverwalk, Buckingham Fountain, Millennium Park, and historic Chicago bridges to quieter natural spaces, urban streets, and industrial environments. Each location is thoughtfully chosen to reflect your style and values. Sometimes the setting is instantly recognizable; other times it’s something unexpected — we work together to match your vibe and vision.

couple standing under CTA train tracks

"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, making him a pleasure to work with from start to finish. 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

Modern, Timeless Engagement Imagery

 

My Chicago engagement photography often blends editorial-style portraits with candid moments. Some images feel cinematic and romantic, others bold and modern, while some carry the refined presence of a fashion editorial or luxury brand campaign. Every photograph is created with intention, balancing light, architecture, emotion, and connection.

"People, I am telling you--this man knows his craft, he is a perfectionist and he cares deeply about taking beautiful, timeless and modern photojournalistic style photos. He goes above and beyond what you expect from a wedding photographer .

The photos were absolutely spectacular and technically gorgeous.

Kenny gives you careful, attentive personalized service that is second to none...It was exactly what we wanted - subtle holiday touches and classic but not cliche Chicago locations."

JEANAH & BRIAN

A Relaxed, Refined Chicago Engagement Experience

Most couples have never been professionally photographed before, and that’s where my experience makes all the difference.

 

I create a relaxed, enjoyable environment that allow you to be yourselves. Every couple featured on this site is real —real relationships, real emotion, real moments—celebrating this chapter of their lives and preserving it beautifully.

 

For couples seeking Chicago engagement photography that feels modern, elevated, and enduring, I invite you to connect and to begin your experience. I would be honored to create something meaningful together.

CHICAGO ENGAGEMENT PHOTOGRAPHER FAQS

Most couples have never been professionally photographed before. You want beautiful, professional, authentic photos of this season of your life! Finding love, getting to know one another, and committing to one another!

As a wedding photographer it's extremely helpful on your wedding day to have couples who understand my cues and direction. Not necessary, but it just alleviates one point of tention. It also builds trust on your end...you will see the completed engagement photos and realize...YOU LOOK GOOD!

We want you to enjoy your wedding photography time on your special day, not worried about how the photos will turn out!

A typical day time engagement session is 90 minutes with up to two locations and up to two outfits.

Rather than just telling you what I think, I like to start off the conversations with: “Are there any locations/vibes you have in mind? Are there any locations that have any sentimental value to you?”

We start there and then collaborate on finding locations that match your answers! I have a vast library of locations to share and am happy to be a resource for you.

Of course! It is my job to help my clients look their best in their photographs.

We all have flattering and unflattering angles. During the session we work together to find the poses that look the best and feel the most natural.

It is the main reasons why I always recommend an engagement session…so you can learn how I direct and be comfortable in front of the lens. This way on your wedding day, you can relax a little bit more, knowing that your photos will look good!

I love how Chicago comes alive at night. Everything looks a little different. A little more romantic. A little more drama.

Taking photos at night is much more technical from a photographer’s point of view. The experience is a little different and so I only offer night photos as an add-on option to a daytime session. You have to learn how to be directed and the posing flow during the daytime session to help our evening time go smoothly!

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

Amalia & Steven

Chicago Engagement Photography

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I'm Kenny Nakai, a Chicago engagement photographer creating beautiful, creative, & timeless imagery since 2007. I would love to capture your love story!

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3334 N Avers Ave #2

Chicago, IL 60618

312-298-9721