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 Chicago proposal spots or needing a photographer 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!

Gorgeous setup by Chicago Luxury Proposals

That look when she realizes this moment is about her…

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


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

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!



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


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-

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!


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

Just that perfect kiss of light from the setting sun-

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.

Took out the sunglasses for a high end luxury fashion vibe

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

A creative way to get a ring shot photo

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

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

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

