A CHICAGO WEDDING BLOG FOR NAKAI PHOTOGRAPHY

One of the Best Chicago Proposal Spots

Chicago Proposal Spots // Olive Park

About a month ago, Jack reached out for help to plan his special moment. They are from Florida and would be visiting Chicago for the weekend. He had some ideas for his proposal and he wanted some advice and perspective from a local Chicago proposal photographer.

We were able to share some photos of our favorite Chicago proposal spots and provide information on each one! He loved the sunset view from Milton Lee Olive Park and found Chicago Luxury Proposals to provide the white flower heart arch backdrop.

If you are needing any help with locations or needing Chicago proposal photography for your special moment – be sure to message us!

Take the time to scroll down to see all of our favorites from their Olive Park proposal!

DISCLAIMERS: We had the most perfect weather, Jack followed my suggestion to avoid the Fri/Sat crowds, and these two love taking photos!

lakefront chicago proposal spots on bended knee

Gorgeous setup by Chicago Luxury Proposals

secret chicago proposal spots heart wreath white flowers arch

That look when she realizes this moment is about her…

lakefront chicago proposal spots walking to location

Jack said he was super nervous – but we would never tell by the photos! And somehow there is a ring box in his pocket?!

chicago proposal spots olive park walking and surprisedlakefront chicago proposal spots olive park heart flower arch white roses

He took his time for them to take in this special moment-

chicago proposal spots sunset at Olive Park

Everything was perfect! Shout out to all the people around who gave Jack and Ana privacy and space. They had the whole platform to themselves – we could not believe it!

chicago proposal spots olive park on bended kneesunset chicago proposal spots at Olive Park white flower arch heart shaped in backgroundsecret chicago proposal spots ring on hand

So picture perfect…almost feels like we are watching a movie!

secret chicago proposal spots kiss and dipsunset chicago proposal spots at Olive Park white flower arch heart shaped in background

These two love taking photos together and have practiced a lot of different poses through the years! They were enthusiastic to try all of my posing suggestions-

sunset chicago proposal spots at Olive Park white roses arch heart shaped in background

Due to the time of day (sunset), these photos required a bit more editing than normal (almost double the time) but it’s worth the effort!

chicago proposal spots sunset at Olive Park lift and hug with white roses arch

chicago proposal spots Olive Park hug with white roses arch

As you scroll through these pictures, you can see why Olive Park is mentioned as of the best Chicago proposal spots!

Olive Park chicago proposal spots white flower heart shaped arch in background

Just that perfect kiss of light from the setting sun-

kiss chicago proposal spots lake michigan

Olive Park has one of the best views of our skyline – almost showing off with the sunset! For those that don’t know…Chicago is known for it diverse architecture and you can see it in the background. That is the John Hancock building towering over the rest of the buildings.

Olive Park chicago proposal spots skyline at sunset in background

Took out the sunglasses for a high end luxury fashion vibe

Olive Park chicago proposal spots skyline at sunset in background

Soooo many gorgeous photos, how do you pick which ones are the best? Let us know which one is your favorite!

private chicago proposal spots skyline at sunset in background

A creative way to get a ring shot photo

private chicago proposal spots skyline at sunset in background

Dancing with the sunset into a new chapter in their lives!

Will You Marry Me? The ring on her hand says it all!

chicago proposal spots sunset will you marry me sign in background

Thank you for having us there to document your special moment at Olive Park, one of the best Chicago proposal spots!

Surprise Navy Pier Proposal Photos // S&Z

Navy Pier Proposal Photos

They were visiting Chicago for the weekend. Unbeknownst to her, it was more than just a nice dinner date. Her family had flown in from the East Coast and had a perfect view from the upper deck for their Navy Pier proposal!

There are so many great emotions captured throughout Zach & Sydney’s photos, be sure to scroll through the whole blog post to see them all!

If you were looking for a Chicago proposal photographer – be sure to send us a message!

navy pier proposal pictures moments before

They were supposed to be arriving for their dinner reservation…and she was caught off guard when he got on one knee!

navy pier proposal photos on bended knee

chicago navy pier proposal surprised expression on bended knee

She said YES!!!

chicago navy pier proposal photos surprised expression on bended knee

And then the emotions slowly began to hit her…

navy pier proposal photos surprised face

surprise navy pier proposal overwhelmed with emotion hug

He still hadn’t put on the ring yet!

chicago navy pier proposal photos hand over mouth with emotionschicago navy pier proposal putting on her finger

After the ring was on…she heard lots of cheering coming from the upper deck

family surprise navy pier proposal photos

She couldn’t believe what she saw-

navy pier proposal happy emotions, hand on her chest

Her family had come into town to partake in the surprise!

family surprise navy pier proposal photos

A photo of the happy newlyengaged!

chicago navy pier proposal photo happy couple flashing ring

Had to take a photos with the ring!

navy pier proposal close up of the ring

Hugs all around for their special moment-

surprise navy pier proposal hugging momchicago navy pier proposal photos grandma looking at ringnavy pier proposal photos showing family her ring

A quick group photo to commemorate the moment-

The setting sun made for the perfect rim light for the Navy Pier proposal photos!

navy pier proposal photos showing off her ring

Took a photo with the iconic Navy Pier Ferris Wheel-

surprise chicago navy pier proposal photos, ferris wheel

She was sooo happy! =)

surprise chicago navy pier proposal photos showing off ring with sunflare in background

Love this photo-

navy pier proposal surprise photos kissnavy pier proposal photography with sunflare in background

We took a few photos with the John Hancock

navy pier proposal photography with John hancock

navy pier proposal photography with Chicago skylinenavy pier proposal surprise photos with Chicago skyline

One last ferris wheel photo to end out their session!

navy pier proposal photography, ferris wheel

Congrats again Zach & Sydney! Hope these photos help you relive your Chicago Navy Pier proposal!

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I'm Kenny Nakai, from NAKAI Photography sharing creating beautiful, creative, & timeless imagery on this Chicago wedding blog since 2007. I would love to capture your love story!

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