CJ reached out to me to help plan and photograph a surprise proposal for Caroline at Milton Lee Olive Park in Chicago. After discussing the timing, location, and logistics, we created a plan that would keep the proposal completely unexpected while also taking advantage of one of Chicago’s most iconic skyline views.

Just as they reached the proposal spot, the sun broke through the clouds behind the Chicago skyline, creating a dramatic backlit scene. While beautiful, the lighting was much stronger than anticipated, so I quickly adjusted my position and recomposed the scene. Being able to adapt to changing conditions is an important part of documenting surprise proposals, where there are no second chances.

After Caroline said “yes,” we spent time exploring Milton Lee Olive Park for an engagement portrait session. The park offers some of the best views in Chicago, combining the city’s skyline, Lake Michigan, walking paths, and open green spaces, making it one of my favorite locations for surprise proposals and engagement photography.

As a Chicago proposal photographer, I help couples not only document the proposal itself but also plan the experience, from choosing the perfect location and proposal timing to identifying the best lighting and coordinating every detail so everything feels natural and stress-free. Every proposal is unique, and my goal is to capture genuine emotion through candid, documentary-style photography while creating timeless portraits you’ll treasure for years to come.

If you’re planning a surprise proposal in Chicago, whether at Milton Lee Olive Park, North Avenue Beach, the Lakefront Trail, Lincoln Park, or another iconic location, I’d love to help you create and capture a memorable experience