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Planning a wedding at The Old Post Office Chicago is an experience in itself. From the moment you step inside, the scale, history, and architectural beauty are impossible to ignore. It’s a Chicago wedding venue that feels iconic yet versatile…equally perfect for editorial portraits, emotional moments, and a celebration that feels completely personal.
This wedding showcased everything that makes an Old Post Office Chicago wedding so special. From rooftop skyline views to heartfelt first looks and a reception full of personality. The day felt layered, intentional, and alive in the best way.
One of the reasons couples are drawn to a wedding at The Old Post Office Chicago is the variety of experiences you can have within a single day, without ever leaving the venue.
From a photography perspective, it’s incredibly dynamic. You can move from historic interiors to modern rooftop views in minutes, which allows the wedding day to feel expansive while still flowing effortlessly.
Some of the standout features include:
A rooftop with stunning Chicago skyline views
A cocktail hour space that truly feels like you’re on top of the city
Ceremony and reception spaces that hold so much history, you can feel it in your bones
Clean lines, strong architecture, and incredible light that photographs beautifully
It’s the kind of venue that doesn’t need heavy décor to feel elevated. The space truly does so much of the storytelling on its own.
While the venue set the stage, it was the people and the moments that made this wedding unforgettable.
One of the most emotional parts of the day was a first look with the bride and her dad, with mom and sister quietly peering over nearby, soaking it all in. It was tender, unplanned, and full of emotion.
There was also a bridesmaids’ first look that radiated friendship and joy, the kind of moment that reminds you how powerful chosen family can be. Later, the couple shared a private first look and letter exchange, grounding themselves together before the ceremony began.
Before walking down the aisle, they also exchanged gifts and handwritten letters with their parents. Emotions were high, tears flowed freely, and the day slowed in the most beautiful way. These quieter moments are often the ones couples remember most, and the ones I believe are just as important to document as the big celebrations.
Cocktail hour took place high above the city, surrounded by sweeping skyline views. This space is one of the many reasons couples love an Old Post Office Chicago wedding.
Adding a meaningful personal detail, the couple incorporated little paper airplanes during cocktail hour, a nod to the groom’s career in the Air Force. It was playful, thoughtful, and completely them. A perfect example of how small details can make a wedding feel deeply personal.
Moments like these are where guest candids truly shine. Laughter, conversations, movement, and connection all unfolded naturally in a space that encouraged guests to linger and enjoy.
The reception was equal parts stylish and fun, a true reflection of the couple’s personalities.
Instead of a traditional cake-cutting moment, they included a meaningful family cake cutting that brought generations together. Espresso martinis fueled the dance floor, while Taco Bell and classic Chicago deep-dish pizza made a late-night appearance (honestly, iconic).
One of the most heartfelt details? Postcards were placed at every guest’s table, each with a personal handwritten message from the couple. It was such a simple yet powerful way to make every guest feel seen and appreciated…and those moments of reading, smiling, and reacting made for some of the most genuine candid photos of the night.
From an editorial standpoint, The Old Post Office Chicago wedding photos have a timeless quality that never feels overdone. The mix of historic architecture, modern design, and expansive city views creates endless opportunities for variety, all while keeping the day cohesive.
It’s a venue that supports:
Emotional storytelling
Editorial portraiture
Candid guest moments
Seamless transitions throughout the day
For couples planning a Chicago wedding who want their day to feel elevated, meaningful, and visually striking, this venue is truly one-of-a-kind.
If you’re dreaming of a wedding at The Old Post Office Chicago and want photography that honors both the emotion and the atmosphere of the day, I would love to connect. Whether I’m documenting the full story or supporting alongside another photographer, my approach is always rooted in empathy, connection, and telling your story honestly.
Chicago weddings hold a special place in my heart, and this venue will forever be one of my favorites.







I had the joy of second photographing this incredible wedding alongside Stacey Vandas Photography!