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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.

Stunning Chicago Skydeck Proposal at Willis Tower

How Matt proposed to Emma on the Willis Tower Skydeck Ledge at sunset. What it took to pull it off, and where we went next.

both kneeling together chicago skydeck proposal

Emma had been waiting a little bit for her ring. A quick scroll through her social media revealed a post using Raye’s “Where Is My Husband” as the song, posted just a few days before Matt actually proposed. She thought it was coming. She just did not know when. Or where. Or how.

What she did not know is that Matt and I had been communicating for months about a Chicago Skydeck proposal that would happen at sunset on the 103rd floor of the Willis Tower. And that a chance encounter at a bar in Iowa had brought her to this moment.

Why Willis Tower, and why the sunset

Matt wanted to propose above the city with the sunset lighting up Chicago behind them. The Willis Tower Skydeck offers private rental opportunities after closing time, which is the option most couples looking for a Willis Tower engagement moment default to. But those rentals happen after the observation deck closes, which means no sunset. No golden hour light. No skyline glowing warm behind the ring.

Matt wanted the sun. So we skipped the private rental and did it a different way.

He purchased two Skydeck tickets, plus a third for me, and we timed the whole thing to arrive on the observation deck as the sun was low in the western sky. Just before closing. Just as the light was doing what it does best.

A private rental gets you the view. A ticketed visit at the right hour gets you the light. For a Chicago Skydeck proposal, the light is part of the show.

suit and yellow dress chicago skydeck proposal at willis tower

The hiding game

Emma and Matt shared a romantic dinner, enjoying Chicago’s downtown restaurant scene. Then they Ubered over to the Willis Tower. I met them at the Skydeck. Well, I say I met them. What actually happened is that I waited outside the elevators, watched them arrive, and then started a game of following them without being seen.

This is harder than it sounds. The Skydeck observation floor is not a large space. You cannot exactly hide behind a pillar for twenty minutes without being noticed. What makes it possible is that everyone at the Skydeck is holding a camera and taking pictures. A photographer with a lens looks like every other tourist. I blended in.

I followed them into the room where you wait in line for your ninety seconds on The Ledge. I had corresponded with an employee at the Skydeck ahead of time who volunteered to help me out. He spotted them right away. Matt in a tailored suit. Emma in an elegant yellow dress. They were dressed for something.

They took their place in line. Matt and I waited with anticipation and, I will admit, a little bit of nerves. \

THE CONSTRAINT-  You get ninety seconds on The Ledge.

This is the thing most couples planning a Willis Tower Skydeck proposal do not know about. There is a time limit on The Ledge. Ninety seconds per group. That means the ring, the words, the yes, the tears, the hug, and the first photographs all technically need to happen inside that window. The good news: the Skydeck staff is understanding when a proposal is unfolding. If you wanted more photos you can  go back to the end of the line for another ninety-second turn if you want more portraits. Plan for ninety seconds, hope for a little grace. That is why the coordination matters so much on a proposal like this.

The moment on The Ledge

After some time in line, they finally reached the front. It was their turn. Emma stepped out onto the glass Ledge, 1,353 feet above the sidewalk below, with the entire city of Chicago spread out beneath her feet.

I came out of nowhere from the other side of the room where I had been hiding. I raised my camera. And Matt got down on one knee.

kneeling at chicago skydeck proposal

Emma had been waiting for her ring, but the moment still hit her like she had not seen it coming at all. Gratitude, love, disbelief, all rushed in at once. The city glowed underneath them. The sun sat low behind the skyline. Matt shared his words. Emma got a little emotional. She said yes.

kneeling at chicago skydeck proposal she's in disbeliefwillis tower chicago skydeck proposal both on their knees with emotionschicago skydeck proposal willis tower looking at each otherchicago skydeck proposal looking at ringeyes watering chicago willis tower skydeck proposal putting ring on finger chicago skydeck proposal willis towerhug after willis tower chicago skydeck proposal

And then all the folks around us erupted in cheers. Strangers who had been waiting in line behind them realized what they had just witnessed and started applauding. We probably went over the ninety seconds. I don’t think anyone minded. That is the kind of flexibility you get when the whole room is rooting for you.

showing off ring at chicago willis tower skydeck proposal first kiss after chicago willis tower skydeck proposal wide city shot at with couple at chicago willis tower proposal

We captured the moment, the ring, the reaction, the embrace, and a few of the wider skyline images that make a Chicago Skydeck proposal so unlike any other proposal location in the city.

sitting on ledge at chicago willis tower skydeck proposal kiss on ledge at chicago willis tower skydeck proposal looking at ring on hand at skydeck willis tower proposal kiss looking north at skydeck willis tower proposal close up laughing on skydeck proposal

Down to the Riverwalk

When it was all done, Matt and Emma decided to extend their shoot into the night. They wanted a few more portraits to remember the day, and since they were visiting from the Pacific Northwest, it felt fitting to take advantage of Chicago’s most photogenic outdoor setting. So we headed down to the Riverwalk.

The light had shifted by the time we got there. The sun was fully down. The city lights had come on. The Wrigley Building glowed white above the river. The bridges lit up in warm amber. Every reflection on the water made the whole scene feel almost cinematic. Like something out of a movie.

lift and kiss during chicago riverwalk engagement at nightsitting on bench chicago riverwalk engagement night timesitting laughing at chicago night time riverwalk engagement on bridge wrigley building in background chicago night time riverwalk engagement

The Riverwalk is one of the most photogenic engagement locations in Chicago, and it works so well at night because the reflections do half the work for you. The river becomes a mirror. Every building becomes a light source. Every corner has a different angle to work with.

yellow dress dancing chicago riverwalk engagement night timeromantic chicago nigh time riverwalk engagementromantic chicago night time riverwalk engagement

Emma kept bursting into laughter and smiles between poses. She was just so happy. Every few minutes she would look at her hand, see the ring, and start smiling all over again. Matt would grin. I would keep shooting.

holding up ring hand smiling chicago riverwalk engagement at nightsitting and cuddling chicago night time riverwalk engagement laughing while sitting chicago riverwalk engagement night time

We were able to capture a wide variety of pictures in a short amount of time because the Riverwalk is just that photogenic. It gave us a completely different feeling from the Skydeck images. The Skydeck was the moment. The Riverwalk was the celebration after.

standing look out during chicago riverwalk engagement at nightdancing twirl romantic chicago evening riverwalk engagement photoclose up smiles romantic chicago night time riverwalk engagement

Planning your own Skydeck proposal?

If you are thinking about a Chicago Skydeck proposal at Willis Tower, a few things are worth knowing from someone who has now pulled one off.

Decide between private rental and ticketed visit early. Private rentals give you the entire observation deck to yourselves but only after closing time, which means no sunset (during the summer). Ticketed visits give you access during operating hours, which means you can catch the light, but you share the space with other visitors. Matt chose the light. Both options are valid depending on what matters most to you.

You get ninety seconds on The Ledge per turn. This is the single most important logistical fact about a Skydeck proposal. The good news is that the Skydeck staff most likely will give a little extra grace during actual proposals, and you can also go back to the end of the line for another turn if you want more portraits. But plan for ninety seconds, hope for a little more, and know that whatever you get on The Ledge, it will be worth it. Your photographer needs to know exactly where they will be standing, exactly what the moment will look like, and exactly which shots to prioritize during those first ninety seconds.

Time your arrival for the light, not the crowds. Late afternoon on weekdays is quieter than weekends. Sunset times vary throughout the year, so time this carefully.

Plan for extended coverage. If you are already spending on a Skydeck ticket and coordinating months in advance, add extra coverage after so you can get more portraits somewhere beautiful. The Riverwalk is a natural next stop. It is a short drive from Willis Tower, it photographs beautifully at any hour, and it lets your new fiancée actually breathe and enjoy the moment after the intensity of The Ledge.

If you want to see other Chicago proposal locations worth considering, I put together a guide to the best Chicago proposal locations with sixteen spots ranging from rooftops to gardens to skyline overlooks.

PLANNING YOUR CHICAGO PROPOSAL?

Let’s plan something they will remember forever.

I’m Kenny Nakai, a Chicago wedding photographer who has been documenting proposals across the city since 2007. From the Willis Tower Skydeck to the Riverwalk to hidden rooftops most photographers do not know about, I help you plan, scout, and execute the surprise, and capture every second of it beautifully. See my Chicago proposal photographer service for pricing and process.

Art Institute Engagement Photos in Chicago // F&Z

An Art Institute engagement,
during a Chicago thunderstorm.

How Farzana and Zuyi turned their favorite date spot into a gallery of engagement photos, days before their wedding.

couple standing in chicago art institute engagement photo

It was one of those hot, humid Chicago summer days where the sky can’t decide what it wants to do. Farzana and Zuyi had been talking about doing their engagement session outdoors, somewhere in nature. But as the forecast got worse throughout the week and the humidity climbed, they made a decision that ended up being perfect: let’s do it at the Art Institute of Chicago instead. One of their favorite date spots when they lived in Chicago. A place they had walked through together many times over the years.

It was definitely the right decision.

couple under arch in chicago art institute engagement photos

A place that meant something to them

Some couples come to an engagement session with a location that’s beautiful but generic. Farzana and Zuyi came with somewhere that had a story. They had been on dates walking these halls. They had photos of each other in front of these same paintings from earlier in their relationship. (like the one below) When the bought tickets for their Art Institute engagement session, we weren’t just picking a pretty backdrop, we were revisiting the place where their relationship had actually deepened.

south asian couple standing in front of impressionist painting

They now live out west, but this was a chance to walk these galleries again, and to do it dressed for the occasion.

Farzana wore traditional South Asian formal wear, honoring her Bangladeshi heritage. Their wedding itself, just a few days later, would blend her Bangladeshi background with Zuyi’s Chinese heritage into a multicultural celebration bringing both families together. The Art Institute engagement session became a beautiful chance to celebrate her side of that story before the wedding day.

It wasn’t just a photo shoot. It was a couple returning to the museum where their relationship had grown up, days before they became husband and wife.

The lobby, the staircase, and the stained glass

We started in the Art Institute’s beautiful main lobby, with its grand staircases leading up to the different galleries. The scale of the space itself is stunning, and the natural light coming in from the windows above gives you flattering, soft coverage that most museum spaces don’t have.

One shot I definitely wanted was in front of the large stained glass artwork. The colors, the geometry, and the light create a stunning backdrop.

chicago art institute engagement photo couple on staircase beneath stained glass

Recreating a scene from La Grande Jatte

One of the most memorable images from the day was in front of Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte,” one of the most iconic paintings in the entire Art Institute collection. Rather than just stand and pose, I asked Farzana and Zuyi sit on the ground below the painting, echoing the scene inside the frame. Two figures sitting together on the grass, mirrored across time and canvas.

The photo would only happen if the couple was up for something a little unusual…like sitting on a museum floor. They saw the vision and were willing to try something outside the standard poses. Love how it turned out!

sitting in front Suerat's la grande jatte engagement photo

Georgia O’Keeffe and the Modern Wing

From there we made our way toward the Modern Wing. On the back stairwell leading up to it, there’s a large Georgia O’Keeffe painting that stops you in your tracks. We stopped there for a photo, letting the scale of the artwork frame them.

on stairwell in front of O'keefe painting art institute engagement picture

Once inside the Modern Wing, we took advantage of what I think is one of the best light situations in any Chicago museum: the large floor-to-ceiling windows facing outward. I had Farzana and Zuyi stand on the elevated walkway for a series of portraits with soft, diffused daylight on their faces. Even with storms building outside, the light through those windows was still stunning.

south asian attire for art institute engagement session

kissing her hand in modern wing at art institute engagement photo

A creative composition on the stairwell

One of my favorite technical shots from the day happened on the stairwell leading down to the first floor. I used a slow shutter speed to intentionally blur the movement of people walking through the frame, while keeping Farzana and Zuyi sharp and still at the center. It creates a sense of the museum moving around them, with the two of them anchoring the scene. Real, but also a little bit dreamy.

couple on modern wing staircase in art institute engagement indoor photo

The spiral staircase

One of the most iconic locations inside the Art Institute of Chicago for both engagement and wedding photography is the spiral staircase. On a bright day, the room is filled with sunlight streaming in from the large windows and lighting up the curve of the staircase itself.

By this time though, the storms had rolled in. It was suddenly dark outside, even in the middle of the afternoon. But that shift actually worked in our favor: the strong architectural lines of the window juxtaposed against the graceful curve of the staircase always makes for an iconic engagement photo.

On spiral staircase for chicago art institute engagement photos

creative chicago art institute spiral staircase engagement picture

Meanwhile, outside, Chicago was getting hit hard.

While we were making beautiful photographs inside, the city outside was in the middle of one of the biggest storms of the summer. Seventy mile per hour winds. Trees knocked down all over Chicago. Power lines pulled out. And yet inside the museum, we could barely tell. It looked like a normal rainstorm through the windows. The Art Institute wasn’t just an indoor engagement session with air conditioning and shelter from the heat. It ended up being genuine shelter from a legitimately dangerous storm.

indoor silhouette, rain outside for a rainy day engagement photo

closeup of hands for south asian couple engagement photo

south asian multicultural couple wearing lavender formal wear

What makes an Art Institute engagement session work

If you’re considering a Chicago Art Institute engagement session, there are a few things worth knowing.

The museum is genuinely one of the best indoor engagement locations in the city. Between the Impressionist galleries, the Modern Wing, the stained glass, the spiral staircase, and the grand entryways, you have essentially unlimited backdrops in one building. In a single 90-minute session, we moved through five completely different visual environments without ever going outside.

Photography permits and rules. Art Institute engagement and wedding photos are allowed with the purchase of a ticket as long as we are not blocking anyone’s path with large equipment. It’s one of the rare instances where you don’t need a permit.

The light changes as you move through the museum. The Modern Wing is bright and airy. The lobby is grand and open. The upstairs galleries are dimmer and more intimate. The spiral staircase depends entirely on the weather outside. Each space needs slightly different technique, and part of what you’re paying for is the photographer knowing how to handle all of it.

A perfect choice, in every way

When we walked out of the Art Institute at the end of the session, the storms had passed. The 70 mph winds had died down. Trees were down all over the city. Streets were flooded in places. But for the 90 minutes we were inside making photographs, none of that had touched us.

It was the perfect choice for an indoor engagement session. as it reminded Farzana and Zuyi of their shared appreciation for arts and culture. Days later, they would celebrate a multicultural wedding blending both of their families and heritages into one ceremony. You can see more from their multicultural wedding day at the People’s Gas Pavilion in Lincoln Park.

Their engagement session at the Art Institute of Chicago was the perfect prelude to that day. A quiet couple of hours in a place that had shaped them, dressed in tradition, walking past the paintings they had walked past on so many dates before.

Planning Your Engagement Session?

Let’s find your favorite place in Chicago.

I’m Kenny Nakai, a Chicago wedding photographer who’s been documenting engagement sessions across the city since 2007. Whether it’s a museum you love, a rooftop with a view, or the neighborhood where you first met, I’ll help you plan a session that actually feels like the two of you. Storms optional.

A River Point Park Proposal in Chicago: Charlie & Evy

river point park proposal on bended knee

When I arrived early for Charlie’s River Point Park proposal, I noticed another guy already at the railing, standing alone with that unmistakable “about to propose” energy. I knew this was a possibility as this spot has quietly become one of the go-to locations for proposals in Chicago, and on this particular Saturday afternoon in June, Charlie’s River Point Park proposal to Evy wasn’t going to be the only one happening on this sidewalk.

The Plan

Charlie had it all mapped out. He wanted to propose at River Point Park, on the west side of the Chicago River as it cuts through the Loop. Although it sits across the river from the Chicago Riverwalk, the park offers one of my favorite downtown skyline views and it’s usually much quieter. This stretch of green space next to Gibsons Italia and the River Point tower is one of the more scenic pockets of downtown.

For Charlie, the spot was personal. He commutes daily from Evanston, taking the Metra into Ogilvie and walking through this exact stretch on his way to the office. He’s seen it in every season and every kind of light. He knew this was where he wanted to ask Evy to marry him.

Charlie’s plan was refreshingly simple. He’d text me from the Metra about twenty minutes before arriving. One of the underrated advantages of taking the train is predictability. No traffic surprises, no rideshare detours, just a reliable timeline that makes coordinating a surprise proposal much easier.

An Unexpected Coincidence

I arrived early, as I always do. That’s when I spotted the other guy at the railing. He had that look I’ve come to recognize after photographing so many surprise proposals. Sure enough, he was there for the exact same reason Charlie was. I quickly texted Charlie to give him the heads up, and he graciously agreed to slow his walk from the Metra so the other couple could have their moment in privacy.

When they were done, the other couple graciously moved aside so Charlie and Evy could have the spot to themselves. Two proposals, one afternoon, one perfect little corner of Chicago. Both wins.

The Moment

Charlie and Evy were on their way to a dinner reservation at Gibsons Italia, and they arrived right on cue. I had already positioned myself on the lawn about 15 feet from the railing, low key and camera ready. To Evy, I was just another person enjoying a beautiful Saturday afternoon in the city.

Charlie pulled her toward the railing and started talking. My guess is he was telling her how much this view means to him, how many times he’s walked past it on his way to work. Then it happened, and it was quick. Evy was expecting a proposal at some point, but not until later in the year, and definitely not on a random Saturday in June. She was ecstatic. As soon as Charlie got down on one knee, she was pulling him back up so she could hug and kiss him. Then he slid the ring onto her finger.

Even though the Riverwalk across the way was packed with tourists, their River Point Park proposal felt almost private. Just a quiet stretch of lawn where two very happy couples happened to get engaged on the same afternoon.

pulling out ring at river point park engagement photosgetting on one knee river point park proposal chicagoon bended knee chicago river point park proposalreaching out for a hug after river point park proposal photoshugging after river point park engagementputting ring on river point park proposal chicagolooking at ring river point park proposalkiss after chicago river point park proposalexcited after river point park proposalcreative photo after river point park proposal chicagolooking at ring river point park proposal photosholding hands with ring chicago river point park proposallaughing after river point park proposal gazing at each other river point park chicago photoslooking at each other river point park engagement photos

Portraits Along the River

After the ring was on and the emotions had settled a little, we took our time walking through the neighborhood for more photos. We made sure to get plenty of shots showcasing her ring and her excitement. We stopped by the Kinzie Bridge and walked through Wolf Point Plaza to get closer to the water, then finished with some classic Chicago bridge portraits.

The weather was that perfect kind of Chicago Saturday: sunny, mild, everything glowing. Couldn’t have planned it any better if I tried.

walking on tracks kinzie bridge engagement sessionkissing on kinzie bridge during engagement sessionsmiles and cuddles on Chicago river engagement photoshootstanding on kinzie bridge during engagement sessionindustrial photo near kinzie bridge during chicago river engagement sessionwolf point chicago riverwalk proposal chicago riverwalk proposal standing on bridgestanding on bridge Chicago riverwalk proposal

 

Why River Point Park Works for a Chicago Proposal

If you’re thinking about a Chicago Riverwalk proposal but want something a little more tucked away from the tourist crowds, a River Point Park proposal is a great alternative. You still get the river, the bridges, and downtown skyline views, but with a much quieter, more intimate feel. And because it’s a short walk from Wolf Point Plaza and the Kinzie Bridge, you can easily add a Wolf Point proposal or a riverside portrait stroll into your day.

For couples like Charlie and Evy who want a spot that already means something (whether it’s part of a daily commute, a favorite lunch break view, or somewhere you’ve walked together many times), River Point Park is hard to beat.

Congratulations, Charlie and Evy! Thanks for letting me be part of this one.


More Chicago Proposal Stories

If you enjoyed Charlie and Evy’s story, here are a few more Chicago proposals worth a look:


Planning your own proposal in the city? Learn more about working with a Chicago wedding photographer or explore my full Chicago proposal photography portfolio.

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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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