From Winter Storm to Winter Wonderland: Luis Fernando & Sara’s Surprise Proposal in Chicago

If you’re one of those people dreaming of a winter proposal with snow everywhere, beautiful landscapes, and a city that looks straight out of a film… Chicago is a YES. Luis Fernando and Sara’s story almost didn’t happen the way we planned—and that’s exactly what made it feel even more magical.

View of the snow from my car on Saturday at 12:30 PM

The plan (and the plot twist!)

We originally scheduled their proposal photoshoot for Saturday, November 29, 2025 at 3:30 PM, late enough for soft afternoon light and early enough to catch a dreamy sunset glow downtown.

When they booked, everything looked fine. But three days before, the weather alerts started rolling in. We considered winging it and hoping the storm wouldn’t be as intense as predicted… but Chicago had other plans. By the time Luis Fernando landed at 1:00 PM on Saturday, it was obvious: the weather was hostile. The storm was the real deal—later confirmed as the snowiest November day in Chicago’s recorded history, with 8.4 inches at O’Hare on Saturday alone (YES! The National Weather Service confirmed it!)

So we made the call to protect the moment: we moved everything to Sunday. And yes—this is exactly why I always include a weather-friendly rescheduling approach in my contract. When life or nature hits, nobody should panic or lose their spot. We just find the next best window and make it happen.

By Sunday morning, the city transformed. After 11 AM, we had clear skies and abundant sunlight reflecting off fresh snow—still absolutely freezing, but visually? Pure winter wonderland. That contrast (chaos one day, cinema the next) is so Chicago.

The “partner in crime” setup

Luis Fernando and I had already met on Zoom a week earlier with his sister, Maria Paula, so we knew exactly who to look for and how the handoff would work. We shared live locations, had a timing plan, and kept everything subtle.

When I spotted them at the meeting point near the west end of the Chicago Riverwalk (one of my personal favorite quiet, intimate spots), Luisfe gave me a tiny nod. I immediately started walking first—“incognito mode”—pretending I was on the phone, with no camera in my hands yet.

That was intentional. The goal was to keep Sara fully relaxed and unsuspecting.

I guided them into the Riverwalk spot, and when I finally pulled out my camera, that was the trigger Luis Fernando was waiting for. Sara’s brain almost tried to make sense of it in the cutest way—she initially thought something like, “Oh! Let’s ask the photographer to take a picture of us!” (Thank goodness she didn’t, because the surprise needed one more second to land.)

And then… the moment of truth.

Emotions were high. The kind of high you can’t direct... only document. Sara said yes, and the joy came in waves: shock, laughter, that “I can’t believe this is real” look, and then the kind of happy that doesn’t sit still. I can't remember how many times Sara said yes, or how many times she stared at her beautiful ring, admiring how her life was going to a new chapter next to Luisfe.

Right after, Luis Fernando called his family in Colombia. They were all far away, but fully present—dying of joy through the phone, celebrating in real time. And Luisfe? He hugged me countless times afterward, grateful that this didn’t feel like “hiring a vendor,” but like having an actual teammate in the plan.

Because that’s the thing: I wasn’t just there to take pictures. I helped shape the whole experience: the spot, the timing, the flow, even the restaurant recommendation for their celebration afterward.

After the photos at Chicago Riverwalk, we kept it simple and cinematic with downtown Chicago holiday energy, especially the nutcrackers on State Street, and finished with portraits at one of my favorite little backdrops: the beautiful door at the Ghirardelli store by State Street.

This whole story brought me back to something I’ve written about before (in my post “Why Working With a Photographer in Chicago Shouldn’t Be Complicated”).

Some photographers can be methodical in a way that feels cold—like you’re being processed instead of cared for. But proposals aren’t spreadsheets. They’re nerves, timing, real emotion, and a million tiny variables (especially in Chicago winter).

My job is to bring calm, confidence, and a little spice—so even couples who swear they’re “not good at photos” end up feeling like themselves… just with a movie-quality memory to keep forever.

Planning a Chicago winter proposal? Here’s what this one proves:

• Weather can be chaotic and still become your best backdrop.

• Choose a spot that feels private (the west end of the Riverwalk is gold for intimacy). You can find some of my favorite spots on my blog post sharing my favorite locations in Chicago.

• Have a photographer who helps you plan, not just pose.

• Build a smart backup plan, because Chicago will always be Chicago.

You can check some of Luisfe and Sara's engagement photos here: