Drayton + Lillian

Milton Lee Olive Park

How to Plan a Winter Proposal in Chicago: Drayton & Lillian's Milton Lee Olive Park Proposal

Planning a winter proposal in Chicago offers a unique and picturesque experience. Drayton's surprise proposal to Lillian at Milton Lee Olive Park in late January serves as a perfect example. The frozen lake and the iconic Chicago skyline provided a stunning backdrop, making their engagement truly memorable.

How Did Drayton Coordinate the Perfect Winter Proposal?

Drayton carefully planned an evening that started with a visit to Navy Pier. As they explored the area, they naturally made their way to Milton Lee Olive Park, known for its wide skyline views. I was quietly positioned, posing as a tourist taking city photos. When they arrived at the park’s landing, I stepped aside to let them take center stage. That’s when Drayton took Lillian’s hands and proposed. Despite the cold January air, they were full of excitement. After the big moment, we took portraits around the park, making the most of the icy, scenic backdrop. The frozen lake added a unique touch only winter can bring. We also captured close-ups of Lillian’s ring, shining against the snowy background.

Essential Tips for Planning a Winter Proposal in Chicago

Considering a winter proposal in Chicago? Here are some essential tips to ensure a memorable experience:

How Should You Dress for a Winter Proposal?

Prioritize warmth and comfort. Dressing in layers is advisable, as it allows for flexibility during photoshoots. You can remove coats for specific shots and put them back on to warm up. Being comfortable ensures genuine expressions in photos.

When Is the Best Time of Day for a Winter Proposal?

Winter days are shorter, so golden hour happens earlier, about an hour before sunset. Midday is another good option since the sun provides a bit more warmth, making colder temperatures more manageable. 

Which Scenic Spots Are Ideal for a Winter Proposal in Chicago?

Milton Lee Olive Park is an excellent choice, but other locations like North Avenue Beach or the Adler Planetarium also offer stunning skyline views. These spots are also along the lakefront, so be prepared for some cooler winds and weather coming off the lake. 

Why Is Monitoring the Weather Forecast Important?

Snow can add a magical touch to your photos, but extreme cold or wind can be challenging. Always have a backup plan in case of unfavorable weather conditions. We can always plan for a backup date or explore some indoor options. I can help with obtaining permits if needed!

What Are Some Warm-Up Spots to Consider Post-Proposal?

After the proposal, heading to a cozy café or a nice restaurant is a great way to warm up and celebrate. Navy Pier is just a short walk away, and some of Chicago’s best restaurants are only a quick cab ride from the park. 

How Can Working with a Professional Photographer Help Plan Your Proposal?

As your photographer, I do more than just capture the moment—I help plan and coordinate the entire proposal to make sure everything runs smoothly. From choosing the best location and timing to discreetly positioning myself so the surprise isn’t spoiled, I’ll guide you through the process. I also keep an eye on weather conditions, suggest backup plans if needed, and provide tips on how to look and feel your best in the cold. Working together ensures that your proposal is seamless, stress-free, and beautifully documented.

Winter proposals have a unique charm, and Drayton & Lillian's story is a testament to that. If you're ready to plan your own winter proposal in Chicago, let’s make it happen!

congrats again!

I’ll be in touch soon with the full gallery, in the meantime enjoy these highlights!

To save the images on mobile: tap & hold a photo and select a save option!