A North Pond proposal, and the reservation trick that made it work.

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

north pond proposal photos chicago on bended knee

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.

sitting laughing chicago water engagement skyline in background

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.

The best proposal spot is not always the most iconic one on the list. Sometimes it is the one where the two of you can just be with each other.

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.

Matthew edited the reservation email.

This part of the alibi was his own idea, and it was a good one. Their actual brunch reservation was for 11am. Matthew edited the confirmation email and showed Sophie a version that said 10am. That gave them a full hour of buffer at the patio before restaurant opened, which assured us the privacy he was seeking. So we had plenty of time for the proposal and initial photos. If you are planning a proposal that involves a restaurant reservation as your alibi, this is a clever trick to use.

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.

box in back pocket at chicago north pond proposal north pond proposal photos lincoln park on bended knee

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.

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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.

skyline in background chicago lakefront engagement photos chicago lake Michigan engagement photos walking holding hands dancing twirl chicago lake Michigan engagement photos laughing together chicago water engagement photos

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.

A People’s Gas Pavilion Proposal, and a moment where nobody quite believed it.

Brandon had his late grandmother’s ring to surprise Chloe at their People’s Gas Pavilion proposal in Lincoln Park. It took her a moment to believe it was real.

peoples gas pavilion proposal aka honeycomb guy on bended knee

Not every proposal goes exactly to plan. When one does, it feels a little like a dream. Brandon and Chloe drove in from Pittsburgh for a weekend in Chicago, and Brandon picked the People’s Gas Pavilion, known locally as the Honeycomb, as the spot to propose.

This is a busy place. The Honeycomb sits along the South Pond in Lincoln Park and it draws tourists, family photo sessions, engagement shoots, yoga classes, wedding ceremonies, and corporate events. The wooden lattice canopy is one of the most recognizable pieces of contemporary architecture in the city. Getting the space to yourselves takes planning.

Brandon and I had been talking about this for months.

A Lincoln Park Proposal Weekend

Brandon and Chloe are the kind of couple who make the most of a weekend away, which was part of why this worked. They planned a Chicago vacation. Chloe had her nails done. She put on a cute dress. Brandon told her they were just going for a walk through Lincoln Park before breakfast. She had no reason to think otherwise since they do this on their other vacations.

The weather cooperated in a way you cannot count on in Chicago. Not too hot. Not too cold. No wind. And critically for a location this popular, nobody else was around the pavilion. We had the Honeycomb to ourselves.

The Honeycomb is not the kind of place you can just walk into and expect privacy. Timing, weather, and a little planning are what turn it from a tourist stop into a proposal spot.

just standing, moments before proposal in the honeycomb in Lincoln Park, Chicago

The joke from the day before

Here is the detail that made this proposal unique. The day before, Chloe had been joking around with Brandon about a scene from The Office, where Jim keeps pulling fake proposal moments on Pam before actually asking her. Chloe told Brandon she was surprised he had never pulled off a fake proposal like that.

Brandon did not say anything to give himself away. He just filed it and moved on.

Twenty-four hours later, on their walk through Lincoln Park, Brandon reached into his pocket and pulled out a ring box. Chloe stared at him. Was this a joke? Was she Pam? He got down on one knee. Chloe kept staring.

stunned look during peoples gas pavilion proposal just looking at each other

The longest few seconds of my career

This is where it got interesting for me. I was unaware of The Office reference. All I knew was that Chloe did not react the way most people do. Her mouth stayed slightly open. Her jaw dropped a little but she was not smiling. Her eyes moved between Brandon’s face and the ring and then back to his face. Then down to the ring again. Then back up.

looking at ring box during peoples gas pavilion proposal aka honeycomb in Chicago

TEN SECONDS OF THIS.

As a photographer who has documented a lot of proposals, I have seen a lot of first reactions. Tears. Nervous laughter. Hands over mouths. Jumping up and down. What I had not seen before was a full stunned silence for this long.

There was a moment where I actually wondered if this was going to be the first proposal in my career to get turned down. My finger stayed on the shutter but I honestly did not know what was about to happen.

What was really happening: Chloe was trying to figure out if this was a joke. Because of the conversation the day before, her brain was trying to process whether Brandon was pulling one of the fake-out scenarios she had mentioned, or whether this was real. She was studying his face for a hint of the punchline.

And then it hit her. This was real. That was actually the ring. This was actually the moment.

excitement on her face - peoples gas pavilion proposal

Her face changed. The smile came. She could not hold it in anymore. She said yes, and the whole scene finally exhaled.

her excited expression at people's gas pavilion proposal

Brandon was equally relieved. Not because he thought she would say no, but because he had been carrying this moment inside himself for months.

kiss after honeycomb people's gas pavilion proposal

hugging after honeycomb proposal in Chicago

The ring belonged to Brandon’s grandmother.

She had passed away just a few months earlier, and Brandon wanted to honor her by proposing with her ring. Kept it hidden through the planning. Kept it hidden in the car on the drive from Pittsburgh. Kept it in his pocket through the walk into Lincoln Park. And now it was on Chloe’s hand, and it was going to stay there.

close up of grandmothers ring after honeycomb proposal in chicago

Watching Brandon after the proposal, you could see how much of his shoulders came down. The weight of carrying a ring that meant that much, for that long, and then finally getting to give it to the person it was meant for. You could see it in his face afterwards.

holding her after lincoln park proposal under honeycomb his first smile after south pond proposal

ring in foreground, kiss in background after peoples gas pavilion proposal

A walk through Lincoln Park, then North Avenue Beach

After the proposal itself, we took our time. Brandon and Chloe walked up onto the bridge just north of the Honeycomb for a series of portraits with the South Pond and the Chicago skyline behind them.

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Then we took a walk over to North Avenue Beach for a few more portraits with the skyline. A few clouds had rolled in over the lakefront by then, which actually gave us a more unique skyline than the standard clear-blue backdrop.

couple walking on bridge at sunrise during chicago lakefront engagement walking on north ave pier during chicago lakefront engagement lift kiss at north ave beach during chicago skyline engagement kiss on cheek during chicago lakefront engagement at North Ave beach kiss at North ave beach chicago skyline in background

Planning a Honeycomb proposal of your own?

The Honeycomb is popular for a reason. The wooden lattice canopy, the way the light filters through it, the South Pond and skyline just beyond, all make for a distinctive backdrop that does not look like anywhere else in Chicago. But that popularity is also the challenge. If you are considering it as your proposal location, a few things are worth knowing.

Time it early. Weekday mornings before 9am are your best window for having the pavilion mostly to yourselves. Weekends fill up quickly, especially in warmer months, and by mid-morning you will be sharing the space with tourists, family shoots, and possibly a yoga class or two.

Weather matters more here than at other locations. Wind through the canopy changes the whole feeling of the space. Overcast light actually works well here because it softens the shadows from the wooden lattice. A perfectly still, mild day is the ideal.

Have a backup plan. Because the Honeycomb is unpredictable in terms of who else is there, it helps to have a nearby second option. The bridge just to the north gives you an entirely different angle with the pond and skyline. North Avenue Beach is a short walk away. Lincoln Park itself has enough variety that if the pavilion is too crowded, we can pivot.

Coordinate with your photographer. This is a public park, but a proposal moves quickly and being able to position ahead of time makes the difference between capturing it well and missing it. You can reach out if you want more details on how to plan a Honeycomb proposal like this one.

If you are considering other locations, I put together a guide to the best Chicago proposal locations with a growing list of spots ranging from rooftops to gardens to skyline overlooks.

Congratulations, Brandon and Chloe. From Pittsburgh to Chicago to a ring that carried a family’s love with it, this one was a good one to be part of.

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 the Honeycomb to the Riverwalk to hidden rooftops most photographers do not know about, I help you plan, scout, and execute the surprise, and capture every second of it beautifully. See my Chicago proposal photographer service for pricing and process.

Stunning Chicago Skydeck Proposal at Willis Tower

How Matt proposed to Emma on the Willis Tower Skydeck Ledge at sunset. What it took to pull it off, and where we went next.

both kneeling together chicago skydeck proposal

Emma had been waiting a little bit for her ring. A quick scroll through her social media revealed a post using Raye’s “Where Is My Husband” as the song, posted just a few days before Matt actually proposed. She thought it was coming. She just did not know when. Or where. Or how.

What she did not know is that Matt and I had been communicating for months about a Chicago Skydeck proposal that would happen at sunset on the 103rd floor of the Willis Tower. And that a chance encounter at a bar in Iowa had brought her to this moment.

Why Willis Tower, and why the sunset

Matt wanted to propose above the city with the sunset lighting up Chicago behind them. The Willis Tower Skydeck offers private rental opportunities after closing time, which is the option most couples looking for a Willis Tower engagement moment default to. But those rentals happen after the observation deck closes, which means no sunset. No golden hour light. No skyline glowing warm behind the ring.

Matt wanted the sun. So we skipped the private rental and did it a different way.

He purchased two Skydeck tickets, plus a third for me, and we timed the whole thing to arrive on the observation deck as the sun was low in the western sky. Just before closing. Just as the light was doing what it does best.

A private rental gets you the view. A ticketed visit at the right hour gets you the light. For a Chicago Skydeck proposal, the light is part of the show.

suit and yellow dress chicago skydeck proposal at willis tower

The hiding game

Emma and Matt shared a romantic dinner, enjoying Chicago’s downtown restaurant scene. Then they Ubered over to the Willis Tower. I met them at the Skydeck. Well, I say I met them. What actually happened is that I waited outside the elevators, watched them arrive, and then started a game of following them without being seen.

This is harder than it sounds. The Skydeck observation floor is not a large space. You cannot exactly hide behind a pillar for twenty minutes without being noticed. What makes it possible is that everyone at the Skydeck is holding a camera and taking pictures. A photographer with a lens looks like every other tourist. I blended in.

I followed them into the room where you wait in line for your ninety seconds on The Ledge. I had corresponded with an employee at the Skydeck ahead of time who volunteered to help me out. He spotted them right away. Matt in a tailored suit. Emma in an elegant yellow dress. They were dressed for something.

They took their place in line. Matt and I waited with anticipation and, I will admit, a little bit of nerves. \

THE CONSTRAINT- You get ninety seconds on The Ledge.

This is the thing most couples planning a Willis Tower Skydeck proposal do not know about. There is a time limit on The Ledge. Ninety seconds per group. That means the ring, the words, the yes, the tears, the hug, and the first photographs all technically need to happen inside that window. The good news: the Skydeck staff is understanding when a proposal is unfolding. If you wanted more photos you can go back to the end of the line for another ninety-second turn if you want more portraits. Plan for ninety seconds, hope for a little grace. That is why the coordination matters so much on a proposal like this.

The moment on The Ledge

After some time in line, they finally reached the front. It was their turn. Emma stepped out onto the glass Ledge, 1,353 feet above the sidewalk below, with the entire city of Chicago spread out beneath her feet.

I came out of nowhere from the other side of the room where I had been hiding. I raised my camera. And Matt got down on one knee.

kneeling at chicago skydeck proposal

Emma had been waiting for her ring, but the moment still hit her like she had not seen it coming at all. Gratitude, love, disbelief, all rushed in at once. The city glowed underneath them. The sun sat low behind the skyline. Matt shared his words. Emma got a little emotional. She said yes.

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And then all the folks around us erupted in cheers. Strangers who had been waiting in line behind them realized what they had just witnessed and started applauding. We probably went over the ninety seconds. I don’t think anyone minded. That is the kind of flexibility you get when the whole room is rooting for you.

showing off ring at chicago willis tower skydeck proposal first kiss after chicago willis tower skydeck proposal wide city shot at with couple at chicago willis tower proposal

We captured the moment, the ring, the reaction, the embrace, and a few of the wider skyline images that make a Chicago Skydeck proposal so unlike any other proposal location in the city.

sitting on ledge at chicago willis tower skydeck proposal kiss on ledge at chicago willis tower skydeck proposal looking at ring on hand at skydeck willis tower proposal kiss looking north at skydeck willis tower proposal close up laughing on skydeck proposal

Down to the Riverwalk

When it was all done, Matt and Emma decided to extend their shoot into the night. They wanted a few more portraits to remember the day, and since they were visiting from the Pacific Northwest, it felt fitting to take advantage of Chicago’s most photogenic outdoor setting. So we headed down to the Riverwalk.

The light had shifted by the time we got there. The sun was fully down. The city lights had come on. The Wrigley Building glowed white above the river. The bridges lit up in warm amber. Every reflection on the water made the whole scene feel almost cinematic. Like something out of a movie.

lift and kiss during chicago riverwalk engagement at night sitting on bench chicago riverwalk engagement night time sitting laughing at chicago night time riverwalk engagement on bridge wrigley building in background chicago night time riverwalk engagement

The Riverwalk is one of the most photogenic engagement locations in Chicago, and it works so well at night because the reflections do half the work for you. The river becomes a mirror. Every building becomes a light source. Every corner has a different angle to work with.

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Emma kept bursting into laughter and smiles between poses. She was just so happy. Every few minutes she would look at her hand, see the ring, and start smiling all over again. Matt would grin. I would keep shooting.

holding up ring hand smiling chicago riverwalk engagement at night sitting and cuddling chicago night time riverwalk engagement laughing while sitting chicago riverwalk engagement night time

We were able to capture a wide variety of pictures in a short amount of time because the Riverwalk is just that photogenic. It gave us a completely different feeling from the Skydeck images. The Skydeck was the moment. The Riverwalk was the celebration after.

standing look out during chicago riverwalk engagement at night dancing twirl romantic chicago evening riverwalk engagement photo close up smiles romantic chicago night time riverwalk engagement

Planning your own Skydeck proposal?

If you are thinking about a Chicago Skydeck proposal at Willis Tower, a few things are worth knowing from someone who has now pulled one off.

Decide between private rental and ticketed visit early. Private rentals give you the entire observation deck to yourselves but only after closing time, which means no sunset (during the summer). Ticketed visits give you access during operating hours, which means you can catch the light, but you share the space with other visitors. Matt chose the light. Both options are valid depending on what matters most to you.

You get ninety seconds on The Ledge per turn. This is the single most important logistical fact about a Skydeck proposal. The good news is that the Skydeck staff most likely will give a little extra grace during actual proposals, and you can also go back to the end of the line for another turn if you want more portraits. But plan for ninety seconds, hope for a little more, and know that whatever you get on The Ledge, it will be worth it. Your photographer needs to know exactly where they will be standing, exactly what the moment will look like, and exactly which shots to prioritize during those first ninety seconds.

Time your arrival for the light, not the crowds. Late afternoon on weekdays is quieter than weekends. Sunset times vary throughout the year, so time this carefully.

Plan for extended coverage. If you are already spending on a Skydeck ticket and coordinating months in advance, add extra coverage after so you can get more portraits somewhere beautiful. The Riverwalk is a natural next stop. It is a short drive from Willis Tower, it photographs beautifully at any hour, and it lets your new fiancée actually breathe and enjoy the moment after the intensity of The Ledge.

If you want to see other Chicago proposal locations worth considering, I put together a guide to the best Chicago proposal locations with sixteen spots ranging from rooftops to gardens to skyline overlooks.

PLANNING YOUR CHICAGO PROPOSAL?

Let’s plan something they will remember forever.

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

CHICAGO WEDDING BLOG

A North Pond proposal, and the reservation trick that made it work.

Ruling out the obvious spots

Matthew edited the reservation email.

The shorts problem

Ten o’clock, on the dot

A walk to the lakefront

Planning a North Pond proposal of your own?

PLANNING YOUR CHICAGO PROPOSAL?

A People’s Gas Pavilion Proposal, and a moment where nobody quite believed it.

A Lincoln Park Proposal Weekend

The joke from the day before

The longest few seconds of my career

The ring belonged to Brandon’s grandmother.

A walk through Lincoln Park, then North Avenue Beach

Planning a Honeycomb proposal of your own?

PLANNING YOUR CHICAGO PROPOSAL?

Stunning Chicago Skydeck Proposal at Willis Tower

Why Willis Tower, and why the sunset

The hiding game

THE CONSTRAINT- You get ninety seconds on The Ledge.

The moment on The Ledge

Down to the Riverwalk

Planning your own Skydeck proposal?

PLANNING YOUR CHICAGO PROPOSAL?

Let’s plan something they will remember forever.