Some couples look forward to a wedding day with 200 people, confetti cannons, or a cake big enough to feed a small army. And if that’s you, I’m here for it! Let the celebration begin! But for other couples, their love stories are written in quiet corners, surrounded by a close-knit group of people, with the city swirling just outside the window. Taylor and Anthony? They’re those people. And their London House Chicago Rooftop Cupola wedding was exactly that kind of magic—honest, naturally playful, and beautifully real.

Vows with a View: London House Chicago Cupola Wedding

What started as a foggy dreary day cleared up just around 3PM when Taylor and Anthony walked out to say their vows and commit to each other in front of their families on the London House Chicago Rooftop Cupola. The sun shone so bright for two of the sweetest people I have ever had the pleasure of documenting. After their ceremony, the crew headed to City Winery on the Riverwalk for a cocktail before their decadent private dinner at The Albert.

I was only with this crew for four hours, but by the end, well, I just didn’t want to leave. What an incredible, down to earth group there to celebrate two people that were clearly made for each other. From their complimenting vows, to their belly laughs on the street and the easygoing way they are in each others presence, it was so easy to see the deep, true love these two have for each other.

Walk with me for a minute. (Metaphorically, unless you’re reading this while actually walking, in which case: multitasking legend.)

Where Old Stories Meet New Love: The Cupola’s Secret Charm

Let’s set the scene: the Cupola at London House isn’t just another Chicago rooftop. It’s a three-story Beaux-Arts crown, perched right where the river hugs the city and Michigan Ave buzzes below. Built in 1923—back when buildings wore statues and architects had names like Alfred S. Alschuler—the Cupola was always meant to be a showstopper.

It’s got griffins, Roman soldiers, and Greek gods carved into its bones. Basically, if you could bottle Chicago’s historic allure and pour it out on the skyline, this would be it.

The best part? The Cupola isn’t just a relic. When London House became a hotel, they wrapped the original Cupola into a multi-level rooftop, so the history stands tall next to glassy, new city views. It’s a little bit Old World, a little bit modern.

And yes, it’s very much available for intimate ceremonies and marriage proposals—just big enough for the people who matter most, and just private enough that passersby can’t crash it by accident. And if you have some room to splurge, book a string quartet because the acoustics are excellent here. Your brother in law on guitar is also absolutely perfect!

Why Couples Love the LondonHouse Cupola (and why I do, too)

Here’s the thing: weddings under the Cupola feel like you’re in on a secret. The city hums below, but up there, things slow down. There’s space to breathe. Space to laugh (or cry, or laugh-cry, as the case may be). And the views? Spectacular.

It showcases a breathtaking, “did we just step into a movie?” panorama. On one side, the river winds past. On the other, the skyline winks at you, like you’re in on a secret.

But honestly, it’s not only about the view. It’s the way the light filters in at golden hour, bouncing off old stone and brand-new glass. It’s how it feels to stand somewhere that’s held a century’s worth of stories. And you get to add your own!

Also, and this is important: the wind will mess up your hair. But I honestly love that for you and the incredible dynamic images you’ll get from it. (However, keep your comfort in mind first and foremost when selecting your hairstyle. If you find hair in your face too distracting, consider a loose updo or pulled-back style.)

Taylor & Anthony’s Wedding Remix

These two decided to remix tradition–and it was perfect.

Even with the short timeline, they snuck away for romantic portraits under the Cupola’s arches and around the city. No audience, no pressure—just two humans, right in that lovely, thrilling moment where nerves and excitement tangle together. Taylor’s laugh echoing off the marble. Anthony looking at her like he had just won the lottery. The city buzzing below, totally oblivious to this once-in-a-lifetime moment.

Then, we wandered London House’s stunning halls for portraits, then headed out to the Riverwalk and through downtown, and (because Chicago) made a pit stop at City Winery. I love this about city weddings: everything’s walkable. Every corner is a new backdrop—a graffiti wall, a bridge, those incredible skyline blues. You can grab a champagne toast, pick up a slice of pizza, or sneak a riverside smooch, and no one bats an eye.

After their ceremony—heartstrings thoroughly tugged—Taylor and Anthony grabbed their closest people and made their way to The Albert, where a private table was set up in the quaint kitchenr. Think warm, glowing light, laughter, hugs from humans who get you, and glasses raised to all the things that brought them here. It was simply beautiful—the best finale to such a joy-filled day.

Downtown Perks: Basically, You Get It All

I’d be lying if I said the Cupola is the only perk of a London House (or riverfront) wedding. The truth? The entire neighborhood is a photographer’s playground, ideal for those in love.

• Photo ops for days: You step outside and boom—Riverwalk, downtown skyline, bridges, historic architecture. No Uber needed, just a pair of comfy shoes (and maybe a snack). For Taylor and Anthony, we wandered from the Cupola to the Riverwalk to the City Winery, catching everything from the sun sparkling on the water to the city’s heartbeat around us.
  
• Views that don’t quit: You get both river and skyline. Sunrise, sunset, blue hour—it’s always cinematic. It’s as if Chicago wants a place in your wedding album.
  
• Guest-friendly everything: Hotels, restaurants, historic landmarks, shopping, nightlife—all within a stone’s throw. Your people can roll out of bed and into brunch, or sip a post-reception espresso along the river, and make an entire weekend of it.
  
• No forced fun: If you want candid, unposed moments, the city is full of unexpected magic. Duck into an alley, chase the last bit of golden hour, dance under the bridges. Chicago’s got you.
  
• Built-in celebration: Your party doesn’t have to stop at midnight. Hit the rooftop bar or keep the laughter rolling at nearby spots. For these two, we ended the night at City Winery with their closest circle—wine, hugs, and the kind of dancing that leaves your cheeks sore from smiling.

Is Long House Chicago Calling Your Name?

If you’re dreaming of a wedding day that feels personal, cinematic, and a little bit like your favorite indie film meets classic Chicago charm, London House Chicago is it. A day where history and modern love collide high above the streets, where you can say your vows with the skyline watching, and where every step—from the London House Cupola to the riverwalk—is an invitation to make your own kind of magic. Taylor and Anthony showed us what’s possible when you let go of the rules and lean into what matters most—and honestly? I’d hit replay on their day in a heartbeat!

I’d love to help you freeze-frame those memories! Have questions about wedding photography? Ask away!