Tropical Winter Proposal in Chicago | Jack and Olivia


March 27, 2024

couple kissing at Garfield Park Conservatory

Proposals are some of my favorite sessions to see on my calendar, and this one was such a fun one to help plan!! Olivia got a complete surprise, and my adrenaline was running high making sure she didn’t see me following them through the jungle paths and other groups of people during this winter proposal in Chicago.

After lots of planning with Jack and deciding between a few different locations, we landed on Garfield Park Conservatory. We all get to stay warm (and dry!!!) in the less-than-predictable midwest weather, we get a little more color than we otherwise might, and we avoid one more obstacle of dealing with all the elements. Win win win!

Our second challenge of the day was hiding Olivia’s arm sling after an unfortunate running accident the week prior, but hey…what is posing for if not hiding an unexpected sling? We wandered around the different rooms at the Conservatory, hitting the palm room, fern room, and desert room (my fave!) before calling it a day and letting these two go make all the phone calls and Face-times to share the news with their people. These two were so much fun to work with! I can’t wait for more proposals to come this year.

Keep scrolling to see more of Jack and Olivia’s surprise winter proposal!

The best part of proposals is all the emotion!!! Happy tears, laughs, and smiles for days–and I’m so lucky to be part of it every time!

couple kissing at Garfield Park Conservatory palm room
couple smiling and laughing at Garfield Park Conservatory

I always love getting lots of pretty detail pictures of the ring–so much thought goes into picking it whether it’s a surprise or a joint effort. These leaves were the perfect spot to show off Olivia’s new ring in a fun way.

Love what you see and want to book your own proposal? Reach out here! Or, see my favorite places for a proposal in Chicago.

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