Chicago Wedding Photographer Blog

Chicago Proposal Photographers w/Andrea + Kate!

Chicago Proposal Photographers Capture THE MOMENT!

Poor Andrea was a little nervous preparing to ask Kate for her hand in marriage. There were so many details to consider! Talk with her father, custom design the ring with RL Jewelers and plan out the details of their morning!

Andrea had search for Chicago proposal photographers and found Nakai Photography…he wanted his Chicago proposal photos to be everything for Kate! Also…with COVID travel restrictions in place, he knew these photos would help tell the story of their special morning!

And so we planned it all out. The Wrigley Building in the background, the perfectly lit Christmas Tree, and a surprised fiancé! This was the photo that Andrea wanted! (scroll down to read more about their Chicago proposal photos!)

chicago proposal photography winter Christmas tree

One their best pictures from their Chicago proposal photos – a picture with the Chicago River in the background and a ring on her finger! =)

chicago proposal photography winter river

A picture of some important hardware. Their ring, their champagne saber (Kate’s first gift to Andrea!), and their bottle of champagne! As Chicago proposal photographers, we are here to tell YOUR story and I think this picture helps tell a little of theirs!

chicago proposal photographers winter Michigan Ave

Chicago Proposal Photos // The Real Story

Now…the first proposal picture at the beginning of this blog post was the one Andrea had envisioned for his special moment…but I was waiting on the other side of the tree! There was some confusion on west facing east and the Tribune Tower…but regardless…Andrea saw where I was hiding out and moved in for his moment!

chicago proposal photographers winter Christmas tree

She said YES! 13+ years as Chicago proposal photographers, and we never tire of the pure joy and emotions that come out after a proposal!

chicago proposal photography winter Michigan Ave

Kate was completely surprised and was all smiles for their special moment!

chicago proposal photographers winter Christmas tree

We can’t predict how we will feel when moments in our life happen. After Kate said YES to his proposal, Andrea was suddenly overwhelmed with emotion. It was so special to witness and I love this tender moment between the two of them.

chicago proposal photography winter Michigan Ave

To all of Kate + Andrea’s family all over the country and globe, here they are – the newly engaged – on Michigan Avenue with our iconic Chicago architecture in the background!


chicago proposal photographers winter Michigan Ave

Chicago proposal photos with the Wrigley Building in the background and the tree where he proposed!

chicago proposal photos winter Michigan Ave

One thing about these two: they love to laugh…and this photo just about sums it up! =)

chicago proposal photographers winter Wrigley Building

They walk this pathway regularly from their home to Michgian Avenue….they love seeing the clock tower from the Wrigley Building!

chicago proposal photos winter Michigan Ave

They wanted to take a few Chicago proposal photos from the their condo – so we made sure to capture a few with their Christmas tree + the John Hancock in the background!

chicago proposal photography winter condo

We proceeded to their rooftop where we were treated to this gorgeous view! You can actually see the tree and spot where Andrea proposed!

Love the symmetry, the Chicago architecture in the background and their silhouette!

chicago proposal photographers winter downtown

Andrea saber’d (is that the correct word?) their bottle of champagne!

chicago proposal photographers winter rooftopchicago proposal photography winter rooftop

Chicago proposal photographers need to get a close up of that ring!!!

chicago proposal photography winter rooftop

Their moment above the city…fitting as they were still on cloud 9!

chicago proposal photographers winter downtownchicago proposal photography winter rooftopchicago proposal photos rooftop champagne

Before ending their Chicago proposal photos, we took a stroll along the riverwalk for a few more pictures! Chicago proposal photographers love our city’s architecture, and the Marina Towers in the background looks great in black and white!

chicago proposal pictures winter downtown

We were on the rooftop of that green mirrored building in the background!

chicago proposal pictures winter downtown

If you were to go on an architecture tour here in Chicago you would learn about the Marina Towers on the left and the Mies van der Rohe building on the right! Also love how they were willing to hop on the bridge for this picture!

chicago proposal pictures winter downtown

It may not be as romantic as a stroll through stone streets of Florence, but our Chicago bridges our iconic to our city! =)

chicago proposal photography winter downtown

Another tender moment as Andrea recounted the emotions he felt when he proposed…needless to say…their families and loved ones were on his heart throughout the morning.

chicago proposal photographers winter emotions

Our Chicago River in the background!

chicago proposal pictures winter downtown river

One last epic photo to finish up their Chicago proposal photos!

chicago proposal pictures winter downtown river

Congrats again Andrea + Kate! We had a wonderful time together capturing your love and your love story together! Thank you for having me!

with love,

your Chicago proposal photographers,

Kenny Nakai from Nakai Photography


Chicago Wedding Photographer


3334 N Avers Ave #2

Chicago, IL 60618