Matt reached out to me several weeks before his proposal to plan a surprise engagement for Kaitlin at the Alfred Caldwell Lily Pool in Lincoln Park. The Lily Pool is one of the most beautiful and intimate proposal locations in Chicago, offering a peaceful setting surrounded by native plants, stone pathways, and picturesque water features.

I waited near the entrance as Matt had a very specific plan. He wanted to propose right away because he knew Kaitlin would start to suspect something if they spent too much time walking around beforehand. As soon as they entered the Lily Pool, he took her hand and got down on one knee. Kaitlin was surprised and, of course, said yes.

After the proposal, we spent time exploring the pathways around the pond and capturing natural engagement photos that showcased their connection and excitement. The Lily Pool offers a unique backdrop that feels tucked away from the city while still being located in the heart of Chicago. The gardens, bridges, and natural landscape create a timeless setting for both surprise proposals and engagement photography.

One of the reasons the Alfred Caldwell Lily Pool is such a popular proposal location is its privacy and romantic atmosphere. Couples can enjoy a quieter experience compared to many of Chicago’s more crowded landmarks while still having beautiful scenery for photographs.

I photograph surprise proposals, engagement sessions, and weddings throughout Chicago and beyond. If you are planning a proposal at the Lily Pool, North Pond, or anywhere in Chicago, I would love to help you plan and document the moment.