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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.

Chicago Private Proposal at Ambassador Hotel

An Intimate Chicago Private Proposal at the Ambassador Hotel 

It was a beautiful day for Yuheon and Mia’s Chicago private proposal! Yuheon chose the Ambassador Hotel, located in Chicago’s Gold Coast neighborhood, and it ended up being the perfect spot. The rooftop offers an unobstructed view of the Chicago skyline from the north — it almost feels like you’re standing in a mountain range looking out at the landscape of buildings and sky.

ambassador chicago private proposal guy on bended knee

The sun was shining, and the clouds gave the sky just the right texture overhead. You really couldn’t have asked for better conditions.

Setting the Scene

Yuheon arrived early to set everything up exactly the way he wanted it for Mia — white roses in vases, candles, the whole rooftop transformed into something intimate and romantic. There was a little sliver of sunlight cutting across the space where they would stand, and I knew that was the spot. The light would catch their faces perfectly the moment he asked her the question.

Once everything was ready, he went downstairs to bring her up. The moment Mia stepped onto the rooftop, she was completely surprised. As a proposal photographer Chicago couples trust to capture this exact kind of moment, witnessing that reaction never gets old. She went from stunned to shocked to pure jubilation in a matter of seconds — and of course, the second the ring was on her finger, she made sure to show it off!

ambassador chicago proposal on rooftop surprised and shocked

laughing at chicago proposal rooftop at Ambassador Hotel

excited during chicago private proposal ambassador

nervous laughing at chicago private proposal rooftop

on bended knee chicago private proposal ambassador rooftop

emotional during chicago private proposal skyline in background

hugging at chicago private proposal ambassador rooftop

kiss after chicago private proposal rootop with skyline in background

emotional during looking at ring during chicago private proposal skyline in background

A Relationship Full of Laughter

One of the defining things about Yuheon and Mia’s relationship is their humor. They genuinely make each other laugh, and it shines through in every single photo from the day. Even in the middle of this huge, life-changing moment, they were smiling, giggling, teasing each other. That kind of natural ease is something you can’t manufacture, and it’s exactly what makes proposal photos feel like them and not just a pretty scene.

laughing during chicago proposalambassador chicago private proposal laughing showing off ringkiss with ring in foreground

For a little while, they had the entire Chicago skyline to themselves for their Chicago private proposal on The Ambassador rooftop. It was a quiet, special time — just the two of them, the city in the distance, and the beginning of everything that comes next.

Capturing the Moment

After the proposal itself, we slowed down and took our time with portraits. I love using the natural light at the Ambassador, especially in the late afternoon. We took some photos with the sun flare behind them, rim lighting them for a more dramatic, cinematic feel.

laughing and having fun during chicago proposallooking at camera sunflare at ambassador chicago proposal rooftop

We made sure to grab a champagne toast too, and I positioned the glasses so the John Hancock shone through the champagne — a little Chicago detail you only notice when you look closely. Those are the kinds of frames I’m always hunting for.

ambassador chicago proposal skyline in background drinking champagnechampagne glasses during ambassador chicago proposal rooftop

I also had to get a dancing picture. A little twirl, a spin, a celebration in motion. You could feel the excitement coming off Mia from the moment she said yes — her heart was overflowing. We finished with a close-up of her ring and a beautiful, quiet portrait of just the two of them on the day they committed themselves to each other.

emotional during dancing at ambassador chicago proposal skyline in backgroundambassador chicago proposal skyline in background on rooftopsoaking the moment in chicago private proposal skyline in backgroundcouple looking out at skyline ambassador chicago proposal rooftop

Why the Ambassador Hotel Is Perfect for a Chicago Private Proposal

If you’re planning a Chicago private proposal, the Ambassador Chicago should be at the very top of your list. The rooftop gives you the Chicago skyline as your backdrop with none of the usual headaches — no crowds, no strangers walking into your shot, no anxiety about someone standing in your spot. The hotel does a great job of offering this private, beautiful space, and that privacy makes a huge difference. The moment gets to feel like it’s truly just for the two of you.

That’s the thing about a great Chicago private proposal location: the venue should disappear into the background just enough for the couple to take center stage, while still giving you that unmistakable Chicago feel. The Ambassador hits that balance perfectly. Privacy, views, romantic lighting, and a skyline that does a lot of the heavy lifting for you.

Congratulations again, Yuheon and Mia! Thank you for letting me be a part of this day. I can’t wait to see what comes next for you two.


Planning your own proposal in the city? I’d love to help. Learn more about working with a Chicago wedding photographer or reach out to start planning your day.

 

A Surprise North Ave Beach Proposal!

A North Ave Beach Proposal

Don called a couple months ago wanting to talk about winter proposal photography. He wanted it to be special for Laura. We talked a bit, threw out some ideas for locations, and talked about possible scenarios.

He hung up the phone, thought about it, and formulated his plan. It would be a North Ave beach proposal! Fingers crossed for good weather towards the end of winter-

We spoke a few more times solidifying the plan as the date got closer and closer.

He recruited his parents and her friends to help make sure this moment was perfect.

As a Chicago proposal photographer…I LOVED photographing all of Laura’s expressions as she was shocked, overwhelmed, full of joy, and full of love. Scroll down to view all 26 photos!

You can read about his experience in his own words: Don’s Five Star Google Review

“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!!”

If you were looking to learn more about my proposal photography services – be sure to send me a message!

north ave beach proposal chicago ring on hand looking at skyline

There’s a lot of detail that went into the alibi, but needless to say, Laura was shocked when she realized the moment was happening! Bonus: the best part of having a North Ave Beach proposal is having our epic Chicago skyline as your background!

north ave beach proposal on bended knee, woman surprised, skyline in background

She stepped back, hands clasped in front of face in disbelief – and then this smile. This smile..this is why I was hired and they have this moment captured…forever

north ave beach proposal chicago on bended knee, woman surprised, skyline in background

north ave beach proposal chicago on bended knee, woman about to kiss

kiss during north ave beach proposal chicago on bended knee

woman surprised during chicago north ave beach proposal

None of these next couple photos are scripted…it was their genuine expressions of love and joy

newly engaged couple standing, foreheads touching at North Ave beach

newly engaged couple kiss and lifting her off her feet after their North Ave beach proposal

Definitely wanted to get a creative ring photo to commemorate the moment!

newly engaged couple kissing holding out hand with her ring on it during their North Ave beach proposal

The newly engaged couple!

Don surprised Laura by having their parents show up – Her mom (who flew in from out of town) was SOOOOO happy for her daughter!

hugging parents surprise daughter at proposalhugging parents surprise daughter at proposal

Her mom sneaking in a little kiss during the photoshoot =)

Before departing, we took a few more North Ave beach proposal photos! This picture almost looks like a cover to their romantic comedy movie!

engagement picture, couple walking at North Ave Beach with skyline in background

Real smiles, real moments…all the feels. As much as I am hired to capture the actual proposal – I love capturing these real expressions-

couple laughing during north ave beach proposal

couple dipping during engagement photo at North ave beach

As our photo time began to dwindle down…her parents departed and I noticed a shift for Laura…a little more relaxed as she soaked the moment in-

couple with foreheads touching

We walked over to a spot where they could sit down to get this phot0-

One last ring photo before I said my last congratulations and departed-

walking showing off ring on her hand during north ave beach proposal

Real talk…this proposal happened on the last day of Feb. It was not terribly cold…but it also was not warm. Chicago weather can be fickle like that. One good thing about colder weather…there are less people around. It was like they had the pier and beach to themselves for their proposal! Don was hoping for a little privacy for their proposal – and they definitely got it! Prime location with a gorgeous view of the Chicago skyline AND minimal people around.

The moment took care of everything else.

The Post Proposal Surprise Celebration

I rushed over to Tapster where Don had gathered their closest friends to celebrate! They have a private room in the back…perfect for their occasion. I wanted to make sure I was able to capture her expression as she walked in and saw everyone-

Loved this moment shared between Don and his sister-

Shout out to all their friends who came out to celebrate!

Congrats again Laura + Don! Thank you for having me there to capture your North Ave beach proposal!

Indoor Winter Love with Chicago Luxury Proposals

Indoor Winter Chicago Luxury Proposals

To say it has been cold in Chicago is an understatement. Despite the frigid temperatures, Emeka surprised the love of his life with a gorgeous rose heart wreath from Chicago Luxury Proposals! As part of their services, they have an indoor location overlooking the river. You get all the winter Chicago vibes from the comfort of a heated room. Shout out to Vanessa and Miguel for an amazing set up for these two!

Hundreds of red roses and candles set the perfect ambiance-

To learn more about our services, be sure to check out our Chicago proposal photographer page!

chicago luxury proposals indoor winter rose heart wreath

We love capturing the moment when Kaitlyn first lays eyes on the proposal set up – look at her smile! Photographer’s insight: We got a little creative and shot through the wreath to frame the couple!

indoor winter chicago proposals couple walking into room

Even though this is a ‘winter Chicago proposal’ – they were able to pause, remove their coats and enjoy this moment – away from the crowds and the cold!

rose wreath chicago luxury proposals woman smiling holding hands

He could take his time share his words of love and commitment to Kaitlyn. They had nothing but time in their private room.

flower wreath chicago proposal couple holding hands

On Bended Knee with Chicago Luxury Proposals

As he got on one knee…he made sure to take his time, so we could capture plenty of photos of their moment with their gorgeous Chicago Luxury Proposals heart wreath!

indoor winter heart wreath chicago proposals guy on bended kneechicago luxury proposals indoor winter rose heart wreathindoor winter heart wreath chicago proposals kiss afterwards

Kaitlyn had all the smiles and giggles afterwards-

indoor chicago luxury proposals during winter laughing holding hands

An indoor winter proposal location with a picture perfect view of the Chicago river-

chicago luxury proposals indoor winter rose heart wreath

The emotions began to hit and a few tears trickled down her cheeks-

flower wreath chicago proposal couple hugging crying

And just to clarify, she did say “YES!”

rose wreath chicago luxury proposals close up of ring on finger

This photo would not be possible outside with the winter Chicago temperatures that day-

indoor chicago luxury proposals during winter by window overlooking riverwalk

Love this photo of her smile and their embrace-

chicago luxury proposals during winter indoors, couple hugging afterwardsflower wreath chicago proposal couple walking in holding hands

That smile on his face is both joy and relief! =)

winter chicago luxury proposals couple together smilingwinter chicago luxury proposals by window overlooking riverwalk indoor chicago luxury proposals during winter by window overlooking riverwalk

Congrats again Emeka + Kaitlyn on your engagement! Hope these photos of your indoor winter setup from Chicago luxury proposals help commemorate your moment forever

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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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