Chicago Wedding Photographer Blog

Chicago Proposal Photography on Riverwalk!

Chicago Proposal Photography on Riverwalk

Nathan found my work when viewing my previous Chicago proposal photography instagram and blog posts and he reached to talk about his upcoming trip to Chicago to surprise Ashley with a ring! Before getting into more details…here’s one of their best Chicago riverwalk proposal photos after she said YES!

chicago proposal photographer riverwalk

Since they had known each other for a long time, Nathan had an idea of what she would like and not like for a proposal. Some where scenic but somehow spontaneous. Nothing elaborate or decorated. She wanted it to feel like it was the spur of the moment surprise!

They don’t live in Chicago, so with 13+ years as a Chicago proposal photographer, I gave my input into a bunch of options! Though the lake front is popular, it can be quite cold this time of year and we wanted to stay near the LondonHouse Hotel, where they were staying.

We settled on this spot along Michigan Avenue for their Chicago riverwalk proposal photos! Here they are heading down the steps…she would have no idea that her life was about to change. =)

chicago proposal photography riverwalk

They admired our beautiful city while taking photos and selfies. Chicago proposal photography is so much fun….the anticipation and emotions are real!

chicago proposal photos riverwalk

Chicago Riverwalk Proposal Photos

And then the moment started! All of a sudden he was on his knee with a box open!

chicago proposal photography riverwalk

And right here…in the middle of our bustling city, Nathan and Ashley had a private moment all to themselves! There was no one around to disturb them or their Chicago proposal photography!

chicago proposal pictures riverwalk

The emotions that unfold are so great to photograph! As a Chicago proposal photographer, I never know how it’s going to go!

chicago proposal photos riverwalk

It’s an emotional moment…not just for the one being asked, but for the one who planned it all out! Nathan was so nervous during lunch when he didn’t have much of an appetite!

riverwalk chicago proposal photographer

Their first hug as fiancé!

chicago proposal photographer riverwalk

All smiles and grins with new jewelry adorning her hand!

The spot for their Chicago Riverwalk proposal photos!

We wanted to make sure to highlight her engagement ring in a picture!

chicago proposal photographer riverwalk

As a Chicago proposal photographer, it’s my job to capture a couple’s relationship…in a way that is real and authentic…and their smiles and laughs make me feel like I accomplished that!

chicago proposal photography downtown

We walked over to the Wrigley Building to take a few photos in front of their Christmas tree to remember the time of year for their Chicago proposal photos!

chicago proposal photography Wrigley building

For those who are viewing these photos from Houston or other parts of the country/world, this is what the Wrigley Building looks like- amazing architecture on our Magnificent Mile!

chicago proposal photography Wrigley buildingchicago proposal photos Wrigley buildingchicago proposal photography riverwalk

Behind them, along the riverwalk, is the restaurant where they had lunch….

chicago proposal pictures riverwalk

Our riverwalk is a newer addition to our city and it is really popular for locals and tourists a like! Makes for the perfect backdrop for Chicago proposal photography!

chicago proposal photos riverwalk

This is one of my favorite spots for Chicago riverwalk proposal photos, and during the summer, you can’t get this picture without boats and a ton of people in the picture!

riverwalk chicago proposal photographyriverwalk chicago proposal photos

Our Chicago bridges are also iconic and really photogenic! I love that these Chicago proposal photos say “Chicago” without being cliche! You have the ‘corncob’ tower on the left, the ‘champagne tower’ on the right, award winning architecture (Aqua building) next to it, as well as Chicago’s newest skyscraper in the middle!

bridges chicago proposal photographer

We were able to capture a lot of amazing pictures in a short amount of time. 13+ years as Chicago proposal photographer helps me maximize our time together!

chicago proposal pictures bridgesbridges chicago proposal photographer

Chicago proposal photographer insights: Love the symmetry, the straight lines, the curved lines leading to the smiling couple in the middle!

bridges chicago proposal photographydowntown chicago proposal photography

Congrats again Nathan + Ashley! So happy for you both! Hope you are enjoying the warmer weather down in Texas and I hope your Chicago riverwalk proposal photos help you relive your moment over and over again!

with love,

your Chicago proposal photographer,

Kenny Nakai


Chicago Wedding Photographer


3334 N Avers Ave #2

Chicago, IL 60618