Sreeni+ Kiara
Milton Lee Olive Park
How to Plan a Memorable Proposal at Olive Park in Chicago
Why is Olive Park a great spot for a proposal?
When Sreeni decided to propose to Kiara, he wanted a location that combined breathtaking views with a quiet, romantic atmosphere. Olive Park, located just north of Navy Pier, was the perfect choice. Known for its iconic view of the Chicago skyline and serene waterfront setting, Olive Park offers a peaceful escape from the city’s hustle and bustle, making it a top spot for couples looking to create an unforgettable proposal moment.
How did Sreeni plan the perfect surprise?
Sreeni and Kiara were staying at one of the hotels at Navy Pier, making it easy to explore the area and spend some quality time before the big moment. They spent the first half of their day enjoying Navy Pier—walking along the lake, exploring local attractions, and soaking in the lively atmosphere. After a relaxed afternoon, Sreeni suggested they take a walk to Olive Park to check out the iconic skyline views.
How did the proposal unfold at Olive Park?
As they made their way to Olive Park, I was already in position. I posed as a tourist, casually photographing the skyline near the landing over the water. This gave me the perfect vantage point to capture the moment while blending into the background. As Sreeni and Kiara moved closer to the perfect spot, I quietly faded into the background and let them take center stage.
Sreeni took Kiara by the hands, looked into her eyes, and proposed. Her reaction was pure joy—she was so incredibly happy! The intimacy of the moment, combined with the stunning Chicago skyline behind them, made the proposal feel like a dream.
What are the best photo spots around Olive Park and Navy Pier?
After the proposal, we took some portraits around Olive Park, capturing the magic of the moment with the iconic skyline in the background. Despite it being a windy day, we managed to get some incredible photos that reflected their happiness and excitement. We also ventured back toward Navy Pier to capture a few more shots with a different perspective of the city.
How do you prepare for a windy day photo session?
Wind can be unpredictable, especially in Chicago, so it’s always best to be prepared. Here are a few tips to make sure your photos turn out beautifully, even on a breezy day:
Pick a hairstyle that holds up against the wind. Updos, braids, or pinned curls can keep hair from flying everywhere. If you’re opting for loose waves, bring a few extra bobby pins or a hair tie just in case.
Choose outfits that work with the wind. Flowing fabrics can create beautiful movement in photos, but avoid anything too lightweight that may get out of control. Heavier fabrics or structured outfits hold up better in the breeze.
Embrace the wind for a natural, romantic look. Wind can add drama and movement to your photos. Flowing dresses and scarves create a dynamic feel that looks stunning in pictures.
Time your session for calmer winds. Wind tends to be gentler in the early morning or late afternoon, making these ideal times for outdoor photoshoots.
Have a backup location. If the wind is too strong, consider sheltered areas nearby or indoor spots that still offer great views while keeping you protected.
How do you plan a proposal in Chicago during March?
March in Chicago can be a little tricky when it comes to planning an outdoor proposal. The weather is unpredictable, ranging from chilly winds to mild, sunny days. Here’s how to prepare for a March proposal and make sure everything goes smoothly:
Prepare for changing weather. Bring a jacket or shawl in case temperatures dip, and have a backup plan for indoor photos if the weather turns. Consider proposing at a location like Olive Park but have a nearby indoor option in mind, like a cozy spot at Navy Pier or a beautiful indoor venue.
Consider timing to avoid crowds. March is a busy time in Chicago, especially around St. Patrick’s Day. If you’re planning your proposal near major events, aim for quieter times, like weekday mornings or late afternoons, to avoid crowds.
Secure your vendors early. March is still part of proposal season, so photographers, planners, and venues can get booked quickly. Lock in your photographer and other vendors early to ensure everything goes according to plan.
Add a personal touch. Incorporate small details that reflect your relationship. Whether it’s revisiting the spot where you had your first date or including a favorite song, these touches make the moment even more meaningful.
Why was this proposal so special?
What made Sreeni and Kiara’s proposal unforgettable was how perfectly it captured their relationship. From the quiet moments walking along Navy Pier to the surprise proposal at Olive Park and the beautiful portraits that followed, every detail came together seamlessly. Even the windy day added a touch of spontaneity that made the experience feel even more genuine.
Ready to plan your perfect proposal at Olive Park?
If you’re thinking about proposing at Olive Park, you’ll be treated to one of the best views of Chicago’s skyline, with a peaceful setting that feels worlds away from the city. Whether you’re looking for a private, intimate moment or planning a surprise with family and friends after, Olive Park offers a stunning backdrop that’s hard to beat.
And if you need someone to capture every moment beautifully, I’d love to be part of your special day. Let’s start planning a proposal that feels like you!
congrats again!
I’ll be in touch soon with the full gallery, in the meantime enjoy these highlights!
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