Let’s talk elopements. Somewhere along the way, eloping got this reputation for being impersonal or rushed. But here’s the thing: an elopement isn’t “less than” a traditional wedding. Eloping can open up a whole world of opportunities to focus on the things that mean the most to you and your partner. It’s about creating a day that’s as personal, intentional, and unique as your love story. If you know me, you know I’m a sucker for a beautifully styled elopement—and a romantic Chicago elopement? I’m all in. Susan and Jesse’s winter elopement and celebration at The Drake Hotel showcases how incredible these intimate celebrations can be. From heartfelt moments to meaningful locations (and yes, a dog in a floral collar!), their day was a love-filled adventure through the Windy City.

So, let’s dive into their story and talk about how to plan an elopement day that feels 100% yours.

Sweet Memories & New Beginnings

One of the best parts of planning an elopement is that you’re not tied to tradition. Forget the standard ballroom or banquet hall—why not choose places that mean something to you? That’s exactly what Susan and Jesse did.

Their day started at the De Paul Chapel, and let me tell you, watching them exchange vows there was everything. Every glance, every word—they were fully present in the moment.

From there, we headed out to hit all their meaningful Chicago spots. I loved this part of the day! We strolled through some of their favorite neighborhoods, stopped by landmarks where they’d spent meaningful time together, and even incorporated a few hidden gems that told their story.

The unique thing about an elopement is that you get to design a day that’s all about you. Think about the places that mean something to your relationship. Maybe it’s the coffee shop where you had your first date, the park where you always walk your dog, or the city skyline you’ve admired together a hundred times. These are the backdrops that will make your elopement feel uniquely yours.

A Wedding Experience They’ll Never Forget

Another misconception about elopements? They’re just quick ceremonies with no room for the fun stuff. But spoiler alert: an elopement is the perfect time to infuse your day with the things you love doing together.

For Susan and Jesse, that meant an epic winter adventure with their dog (who, by the way, looked amazing in her floral collar). Their pup was right by their side every step of the way, from their ceremony at DePaul Chapel to every photo stop across the city. These two embraced the winter vibes like pros, and the chilly air only added to the cozy, romantic feel of the day.

Your elopement day should be filled with the things that bring you joy as a couple. Love hiking? Head to the mountains. Big on brunch? Treat yourselves to mimosas and waffles after saying, “I do.” Obsessed with your dog (because, same)? Bring them along! Elopements give you the freedom to do it your way, no matter what that looks like.

Celebrating with Their Inner Circle

One of the things that stood out to me most about Susan and Jesse’s day was how connected they were. With no big crowd or jam-packed timeline, they had the space to simply be with each other and soak in the fact that they were finally married (cue all the happy tears).

After capturing photos at their favorite Chicago spots, we ended the day at The Drake Hotel, where their family was waiting to celebrate with them over dinner. It was intimate and low-key in the best way possible and the perfect way to end their day.

That’s the beauty of an elopement: there’s no pressure to entertain hundreds of guests or stick to a rigid schedule. It’s all about creating a day that feels meaningful, intentional, and full of love, whether that’s a quiet dinner with family or a spontaneous night out on the town.

3 Steps to Planning a Personalized Elopement

If there’s one thing I want you to take away from Susan and Jesse’s story, it’s this: an elopement doesn’t mean sacrificing the personal touches that make a wedding special. In fact, it’s the opposite.

Eloping gives you the freedom to:

• Choose a Location That Speaks to You: Whether it’s a bustling cityscape, a serene spot on Lake Michigan, a boutique hotel, an art studio, or your cozy backyard, the location is entirely up to you. Forget cookie-cutter venues—you can say your vows in a place that holds real meaning for your relationship. Pro Tip: Make a list with your partner of places that are meaningful to your relationship. They don’t have to be glamorous—sometimes, the quaint, most unassuming spots spark the best memories and make your day truly yours.
• Curate the Details that Matter to You: From what you wear to how the day unfolds, elopements are all about the little details that reflect your unique story. Love a non-traditional outfit? Rock it. Want to write your own vows and share them at sunset? Do it. Susan’s gorgeous modern gown and winter coat paired with Jesse’s velvet suit showed off their stylish side, and their portraits are art. Maybe you want to focus on the food or a shared experience with your crew. When you embrace what feels right for you, magic happens.
• Spend the Day How You Want: Traditional timelines? Toss them out the window. Eloping means you can design a day that’s just as adventurous or relaxed as you want it to be. You can spend the morning together sipping coffee, take your time wandering through your favorite spots, savoring a meal at your favorite restaurant, or even end the evening with a cozy fire and dessert. There’s no “right” way to elope.
• Embrace the Season: Winter weddings can be so magical—we’re talking soft snowflakes, cozy vibes, and chic winter fashion. Instead of trying to fight the season, lean into its charm and make it part of your love story. Pro Tip: If you’re eloping in a specific season, think about how you can celebrate it through your outfits, flowers, or even your choice of activities. Winter hot cocoa bar? Yes. Summer picnic in the park? Also yes.

What Does Your Dream Chicago Elopement Look Like?

Whatever season you’re in, let it add to the story of your day. When you strip away the expectations and focus on what matters, your wedding day becomes even more personal and meaningful. Susan and Jesse’s elopement wasn’t just about saying, “I do.” It was about celebrating their love authentically and intentionally in a way that felt true to who they are. And isn’t that what a wedding should be about?

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