CHICAGO WEDDING BLOG

Matthew planned a quiet North Pond proposal in Lincoln Park, using a brunch reservation as the alibi. Sophie had no idea.

When you are planning a Chicago proposal, it helps to have an anchor point. Something to build your proposal around. For Matthew, that anchor was a celebratory brunch reservation at 11am at the North Pond Restaurant in Lincoln Park.

The proposal itself would happen nearby. We just needed to figure out exactly where.

Ruling out the obvious spots

Matthew and I talked through a lot of location options ahead of time. Lincoln Park has some great proposal spots, but the deciding factor for Matthew was privacy. Sophie was going to want the moment to feel intimate, not a public spectacle. On a Sunday morning in Chicago, most of the obvious Lincoln Park locations get busy fast.

The Honeycomb at People’s Gas Pavilion draws tourists and photo sessions. The South Pond bridge is popular. North Avenue Beach gets packed on a nice weekend. All beautiful, but not what Matthew was looking for.

So we came back to North Pond, a less crowded section of Lincoln Park. There is a small concrete patio in front of the restaurant, with a couple of benches where guests wait for their reservations to be called. It offers a nice view of the Chicago skyline across the water, and, critically for Matthew, it is not a crowded place. Most people who pass through are just on a walk, jogging, or heading to the Lincoln Park Zoo or Peggy Notebaert Nature Museum.

One thing worth flagging: while you can propose on this patio, North Pond restaurant has an outdoor patio for diners, so proposing before they open is the best option if you don’t want to have 30 people mid-brunch, watching you.

The shorts problem

With the timing and location sorted, Matthew had one more problem to solve. He needed to get the ring box to the location without Sophie noticing. Sophie is an observant partner, which meant a front pocket ring box bulge was not going to fly. The back pockets of most of his shorts were too tight to hold the box discreetly.

So Matthew went through his closet the day before, trying on every pair of shorts he owned, testing each one for whether the ring box would fit invisibly in the back pocket. He found one pair that worked. That is the pair he wore that morning.

On the walk over, Sophie had her suspicions. She looked at his front pockets, saw nothing unusual, and convinced herself it must not be today. After all, they had a reservation to get to.

Ten o’clock, on the dot

I got to North Pond early. Parking around Lincoln Park on a Sunday morning can be a hassle, and I wanted to be settled before Matthew and Sophie arrived. It was a beautiful morning, the pond was full of geese moving around, and I had plenty of time to relax at the exact spot on the patio where the moment would happen.

Matthew had told me he would arrive at 10am. He walked up at 10am on the dot. Pretty impeccable timing.

I was ready. When I saw Matthew reach for his back pocket, I knew it was time.

Sophie was surprised in the best way. Her emotions came through immediately in every photograph. The ring, once it was on her finger, kept catching her eye. She could not stop looking at it. She kept smiling. Behind the smile you could see her working out the whole picture in her head. How did he pull this off? The reservation was part of it? Who is this photographer? And the ring is beautiful.

Matthew, for his part, exhaled and had a smile of satisfaction on his face. He was able to surprise her after all.

A walk to the lakefront

After the moment settled and we talked through the rest of the shoot, Sophie mentioned she liked the idea of including the lakefront skyline in their portraits. She and Matthew live near the lake and walk their dog along the lakefront paths every day. It is part of the rhythm of their life together.

What I did not know at the time is that they would be moving soon. Away from the lakefront neighborhood they had called home. Including Lake Michigan and the Chicago skyline in their proposal photos would mean so much to them. These pictures would be the perfect ending of this chapter, in the exact place where they had lived it.

Planning a North Pond proposal of your own?

North Pond is a quieter Chicago proposal location, especially for couples who value privacy over a widely recognized landmark. A few things worth knowing if you are considering it.

The waiting patio is the spot. The small concrete gathering area in front of the restaurant entrance, with the benches. This is where the proposal should happen. It does take some finesse to make sure the benches are not in the frame when possible.

Use the restaurant reservation as your anchor. A brunch or dinner reservation gives you a natural, unquestionable reason to be at that specific spot at that specific time. If your partner would question a random walk through the park, a restaurant reservation solves that entirely.

Build in a buffer. Matthew’s email edit gave him a full hour before the real reservation. You could do this a lot of ways, but the key is having enough time for the proposal and a few initial photos without having to rush to your actual seating time.

Arrive early to account for the crowds. Parking around Lincoln Park on a nice weekend day takes time due to the popularity of the lakefront, zoo and nature museum. I always try to be settled at the location well before the couple arrives. The last thing you want is your photographer arriving late.

Skyline access is a short walk away. If you want to extend into a portrait session, the lakefront paths east of North Pond are just a few minutes away. You can get skyline shots without needing to drive anywhere else.

If you are considering other Chicago proposal locations, I put together a guide to the best Chicago proposal locations covering rooftops, gardens, lakefront spots, and hidden corners across the city.

Congratulations, Matthew and Sophie! It was perfect!

PLANNING YOUR CHICAGO PROPOSAL?

Let’s plan yours together.

I’m Kenny Nakai, a Chicago wedding photographer who has been documenting proposals across the city since 2007. From quiet corners of Lincoln Park to hidden rooftops most photographers do not know about, I help you plan, scout, and execute the surprise, and capture every second of it. See my Chicago proposal photographer service for pricing and process.