Sam & Courtney’s Surprise Engagement Proposal in Grant Parks South Garden in downtown Chicago
On a warm summer day, Sam led Courtney through the garden paths near Buckingham Fountain. With the Chicago skyline rising behind them and the greenery in full bloom, the setting felt effortlessly romantic. At just the right moment, Sam got down on one knee. Courtney’s reaction was instant—shock, laughter, and happy tears all at once. Those genuine emotions are what make surprise proposals so powerful, and why capturing them professionally matters. One of my favorite moments was when Courtney realized what was happening she instantly took off her purse and threw it to the side so that it wouldn’t be in the photos. Don’t get me wrong I love a flawless photo but at the same time I love to see all the candid-ness of a moment that can be repeated. I like to see the purse on her arm and the ring box making a big square impression in his pocket as they arrive for the proposal. All those details make the moment real and show that the moment is real. Sometimes if you take out all the noise from a photo it looks too good to be true. In this case I loved documenting Courtney trying to make the moment pristine and that in itself told a fun story. I admire Sam & Courtney’s ability to let their emotions flow in their special moment. Courtney was beaming and she couldn’t keep it in.
If you are looking to propose in the South Garden in Grant Park don’t forget the Fountain doesn’t turn on until the second weekend in May. Also note that if you are looking for photos with the tallest fountain spray, you have to be there at the top of the hour. The impressive spray only lasts 15-20 mins so plan accordingly.























For tips on planning a surprise proposal in Chicago, check out my blog on How to Plan a proposal here. For help finding the perfect location for your surprise proposal, check out my blog on popular Chicago locations here. For specifically skyline locations , Click here to see a list of skyline locations.
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