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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.

kenny nakai chicago photographer in tuxedo on dark backdrop

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.

 

Welcome to my Chicago wedding blog, where I share my latest work and the deeper stories behind the photos. I hope you find inspiration here and connect with the feelings I had when I created each one.

CHICAGO WEDDING BLOG

REAL STORIES.

REAL VENUES.

REAL MOMENTS.

chicago skyline engagement night

It's been quite the journey since I started this Chicago wedding blog in 2007. Photography is more than something to post on social media. It's a time capsule. Stopping. Freezing. Holding a moment forever.

 

There is no greater privilege than being trusted to preserve these moments for the people I love working with.

 

Wedding photography has brought me to the rooftop Cupola at The LondonHouse and on to the turf at Wrigley Field. Not just documenting people, but our ever-evolving city, one frame at a time. One love story at a time.

A helicopter wedding entrance, flown in by the groom’s own father.

Callie and Jared were married at Twin Orchard Country Club, with a ceremony entrance by helicopter, a quiet tribute to Callie’s late sister, and a fire dancer who kept the reception going.

Callie and Jared met because his parents insisted. Jared’s mom and stepdad struck up a conversation with Callie at a business networking event and walked away certain she was the one for their son. There is usually a polite amount of doubt built into that kind of parental prediction. This time, they were exactly right.

Family, from the very start

Callie is aunt to five kids, and she wanted them close to her throughout the wedding. When I got married, I had seven nieces and nephews standing in as my ring bearers and flower girls, so I knew exactly what that felt like from the other side of the camera. It was fun to watch her nieces and nephews move through her wedding day the same way, proud of their jobs and a little wide eyed about the whole thing.

Cars, cowboy hats, and the things they love

Jared and Callie built pieces of the day around what they actually love. Cars, for one. They set up a small showcase of vintage and modern sports cars in two rows, so guests walked between them on the way to the ceremony and again on the way back for cocktail hour. We made sure to get a few photos with them.

They love horses too. Jared, his groomsmen, and both fathers wore custom cowboy hats, with the wedding date seared into Jared’s.

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Then there was the helicopter

Jared’s dad and stepmom are both pilots, and between the two of them, they had a helicopter. There was really only one way to put that to use: fly Callie in for her own ceremony. It wasn’t just a circus trick…it was a meaningful moment of the two families coming together.

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Chalk cannons helped accentuate their ceremony exit!

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Wedding Details:

Planner and Coordinator: Events by Shaun Rajah
Photographers: NAKAI Photography
Ceremony and Reception Venue: Twin Orchard Country Club
Florals and Decor: Juliet Tan Floral Design
MUA and Hair: The Bridal Beauty Team
Band: Sway Chicago
Transportation: Midwest Transitsystems
Gown: Bella Bianca Bridal
Content Creation: La Novia Creations

A day with this many moving parts doesn’t come together on its own. Callie and Jared got ready at separate locations across Chicago, guests were shuttled from downtown out to Long Grove, and somewhere in between all of that was a helicopter and a fire dancer. Shaun and his team, along with staff at Twin Orchard Country Club, kept every piece of it running smoothly.

Getting Ready Photos in Chicago

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Carrying Erica with her

Callie carried her late sister Erica with her all day. Her veil was monogrammed with a private message, and she signed the ketubah with a multicolored pen that had belonged to Erica since they were kids. Her sister, Chelsea, also honored her presence during her reception toast and an emotionally moving slideshow.

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A first look near North Avenue Beach

Family shaped the wedding party too. Callie and Jared brought their siblings into it, put their nieces and nephews to work as ring bearers and flower girls, and kept both sets of parents, including Callie’s stepmom, close for photos all day.

For the first look, we went to North Avenue Beach. On paper, it’s an unexpected choice for a couple getting married thirty miles north in Long Grove. But it wasn’t random to Callie. She and her siblings used to spend time there with their late grandmother, right outside her home, and those memories mattered enough to bring along on her wedding day.

The most meaningful locations on a wedding day aren’t always the most photogenic ones on paper. They’re the ones that mean something.

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The Helicopter Entrance

Landing a helicopter on a golf course takes more coordination than people assume. After the ketubah signing, Callie, her parents, and I were shuttled to a regional airport where the helicopter was waiting. Jared’s dad walked us through every safety check before we were escorted out to the tarmac.

I had never been in a helicopter before this. Twenty years into this job, it’s still one of my top five moments as a wedding photographer. Listening to the pilots talk to each other through their headphones, watching the ground drop away beneath us. I wish I’d thought to record the radio chatter.

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The flight from the airport to the golf course only took two to five minutes. Conditions were about as good as we could have asked for, clouds out in the distance but clear skies right where we needed them. We made such good time that the pilots circled the ceremony a couple of times while guests pulled out their phones to film from the ground. Then came the landing, the hugs, and Callie taking her place to walk down the aisle.

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events by shaun rajah leading ring bearers to ceremony

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The most powerful moment was a surprise to the bride and groom. During her sister’s toast, an old video played, one from Callie’s bat mitzvah, of Erica talking about Callie’s future wedding. She couldn’t have known what she was describing back then. Hearing it, years later, in the middle of Callie’s actual wedding, felt like something out of a movie, the kind where a character watches a moment from the past connect directly to where they’re standing now.

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A voice from the past, at the exact right moment.

Chelsea tracked down the video and made sure Erica had a place at the reception. It gave Callie’s late sister a presence in the room she would have wanted, and it’s a moment Callie’s family will hold onto long after the wedding day itself.

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Chelsea…wow…what a moment.

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A reception with room to spare

A golf course reception means space, and Twin Orchard Country Club made good use of it. One of Jared’s closest friends, Ian, put on a fire dance for the whole reception, working sticks, poles, and whips trailing flame across the open lawn.

At one point, Ian swallowed a fireball, then invited Chelsea to try it herself. Not something most people get to say they’ve done.

There are things in life you can say you did. Chelsea can now say she swallowed fire, at a wedding.

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Congratulations, Callie and Jared – what an unforgettable day, for all the right reasons.

Planning a Wedding at Twin Orchard Country Club?

Let’s talk about your day.

I’m Kenny Nakai, a Chicago wedding photographer who has photographed weddings at Twin Orchard Country Club and across the North Shore since 2007. I would love to hear what you are envisioning, helicopter optional. Let’s start a conversation!

Chicago Rooftop Engagement Photos // C&M

People meet in all kinds of ways. Apps. Mutual friends. Workplace coincidences. But Chris and Mary Ellen met the old-fashioned way…at a gathering. A rooftop gathering, specifically, at their own apartment building in Lincoln Park.

The Eugenie Terrace on the Park is an “older” building on Clark Street, it kind of feels like it has been there for a while. But it has something more reflective of “newer” Chicago apartments: a multilevel rooftop with a pool, a lounge, and a grill. It’s a space where conversations can happen easily. Theirs did. And it turned into something more.

After that first conversation came more time together.  Long walks through Lincoln Park with Chris’s dog, which Mary Ellen was more than happy to join. One thing led to another the way it does, and here we are. His dog was a perfect wingman.


How the Rooftop Became the Session

When we started talking locations for their engagement session, I casually asked if they knew of any rooftops, or if their building happened to have one. They said yes, and then they paused. That’s where we met!

They hadn’t even thought of it themselves. Once they said it out loud, there was no question. We had to shoot there.

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Chris and Mary Ellen are getting married next year at Café Brauer in the Lincoln Park Zoo. Because we knew we’d be near the South Pond area on their wedding day, we made a conscious decision to save that stretch of the park. Instead we started their engagement session somewhere else: North Avenue Beach.

As their Chicago wedding photographer, it was helpful for them to learn how I flow through different poses and spots during their engagement session.


North Avenue Beach — September Light

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September in Chicago can be unpredictable, but that afternoon gave us exactly what we needed. It had been raining in the morning. The sun had been hiding behind clouds for most of the day, and right as we arrived at North Avenue Beach, it broke through. The skyline lit up. The timing was perfect.

We started on the pier, which stretches out over the water and puts you right in front of one of the best Chicago skyline views anywhere in the city. At the end of the pier there’s a metal structure about forty feet tall with a red light on top. Part navigational marker, part accidental sculpture. It makes for a unique photo with the couple against the skyline, a detail most people walk past without noticing.

Then Chris and Mary Ellen took their shoes off. This was not part of the photo timeline. But it was stunning. They walked along the sand, right at the edge of the water, just the two of them. It was one of those unplanned moments that ends up being a favorite from the whole session.

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The Rooftop at Sunset — The Eugenie Terrace

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We made our way back to their apartment on Clark St with enough time to change outfits and get up to the roof before the sun dropped below the skyline. Chicago rooftop engagement photos live and die by timing, and we timed it perfectly.

The Eugenie Terrace’s rooftop looks west over Lincoln Park and the city. We shot as the sun crossed the horizon, the skyline going from gold to amber to something warmer. Then the sun went down and the sky turned pink. That short window of time after sunset when everything softens and the light turns the sky into a painting. It was romantic just to be there witnessing their moment of solitude.

There is something meaningful about photographing a couple on the exact spot where their story started. They both noticed it. I did too.


The Riverwalk at Night

We finished the session downtown on the Riverwalk after dark. The city at night is a completely different subject than the city in daylight. Moodier, more cinematic, and romantic in a way that’s hard to manufacture during the day.

We worked through some of the most recognizable architecture in Chicago: the Wrigley Building lit up white against the sky, the twin corn cob towers of Marina City reflected in the river, the classic lamp posts lining Wacker Drive. Each one is a little piece of the city’s personality.

We closed the night at the Chicago Theatre sign on State Street. There’s significant construction around it right now as they renovate the nearby Red Line stop, but we found the angle anyway. The sign is iconic enough that nothing can really take away from it.

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Chris and Mary Ellen, you made this easy. From the pier to the rooftop to the river, it was a night that felt like Chicago at its best. I cannot wait for Café Brauer next year!

If you are planning a Chicago engagement session and want something that actually feels like your life in this city, not just the tourist locations, I would love to hear about it. Let’s connect.

A wedding surprise nobody saw coming, not even the bride.

Halle and Jordan married at the Radisson Blu Aqua, inside one of Chicago’s most recognized buildings. Then a full marching band walked into the reception.

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Halle and Jordan met as kids, back when their dads coached T-ball together. Years later, in middle school, they saw each other again at a bar mitzvah, and Halle gathered the courage to walk across the dance floor to talk to him. Their friendship started that night and never really stopped.

Most couples meet after each person has already lived through life’s ups and downs on their own. Halle and Jordan lived through theirs together. Their relationship deepened by their shared experiences. By the time they got married, so many of their friends and family said the same thing: it was never a question of if, only when. That “when” finally arrived a couple weeks ago, at the Radisson Blu Aqua Chicago Hotel.

Shout out to Johnna from Great Events, Tara from the Radisson Blu Aqua, and Mal from HMR Designs for making this wedding a magical night for Halle & Jordan!

Wedding Details:
Ceremony and Reception Venue: Radisson Blu Aqua Hotel, Chicago
Photographers: NAKAI Photography
Planner & Coordinators: Johnna from Great Events, Inc
Florals & Decor: Mal from HMR Designs
Band: Lakeshore Encores
Hair: Erin Ahern
MUA: Kelly La Banco
Gown: Ines Di Santo

A wedding inside one of Chicago’s most recognized buildings

The Radisson Blu Aqua sits inside the Aqua Tower, an 82 story building in the Lakeshore East neighborhood designed by architect Jeanne Gang. Completed in 2009, the building is known for its curved, rippling concrete balconies, inspired by the striated limestone formations found around the Great Lakes. It was named Emporis Skyscraper of the Year the year it opened, and it remains one of the most awarded buildings in the city.

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Halle wore an Ines Di Santo gown with the perfect matching veil (the veil comes later)bride Radisson blu aqua hotel chicago wedding getting ready bride photo Radisson blu aqua hotel chicago wedding close up of bouquet Radisson blu aqua hotel chicago wedding smiling bride Radisson blu aqua hotel chicago wedding

Halle’s first look with her dad was an emotional one for both of them. Watching her wipe a tear from his eyes is one of my favorite moments from the entire day.

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Her friends were stunned when they saw her for the first time!

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The guys were busy getting ready themselves

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Love this candid moment of Jordan’s mom touched his nose during his own getting ready photos. Small moments, but the kind that end up meaning the most later.

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We took advantage of their private outdoor terrace for their first look

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The Radisson Blu Aqua is an award winning building, and it would have been a mistake not to use it. I coordinated with my associate photographer to build one portrait specifically around the architecture, the rippling balconies photographed from below, with Halle and Jordan built into the frame. It is one of my favorite images from the day, and one that could only happen at this specific hotel.

Radisson blu aqua hotel chicago wedding couple on balcony

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 Mal from HMR Designs brought the whole vision to life, green pipe and drape paired with white, pink, and green florals: roses, hydrangeas, calla lilies, and more.

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A surprise nobody saw coming

Halle had always dreamed of having a marching band at her wedding. Her dad decided to make it happen, and somehow kept it a secret from her through the entire planning process. During the reception, the Lakeside Pride Marching Band walked in unannounced but definitely heard. Halle had no idea. Neither did any of the guests. The reaction across the room was priceless, and I still do not know how her dad, or her planner, managed to keep something that big under wraps for that long.

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Hidden from the bride, until the exact right second.

A real shoutout is owed to Johnna from Great Events Inc, who helped plan and coordinate the whole wedding and somehow kept a marching band hidden from Halle until the perfect moment.

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Lakeshore Encore, part of the Gold Coast Events family, played the rest of the night and kept the dance floor full of energy.

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And as with every Great Events wedding I have photographed, the dessert table was a genuine highlight to close out the night.

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Congrats again Halle + Jordan! Loved photographing your wedding, from the tears in your bridal suite to the surprise marching band – it was everything!

Planning a Wedding at Radisson Blu Aqua?

Let’s talk about your day.

I’m Kenny Nakai, a Chicago wedding photographer who has photographed weddings inside the Aqua Tower many times, along with venues across the city since 2007. I would love to hear what you are envisioning, marching band optional. Inquire for more information!

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I'm Kenny Nakai, a Chicago wedding photographer creating beautiful, timeless imagery since 2007. For couples who value artistry, authenticity, and the moments that last forever.

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