Hannah & Bobby’s Chicago Wedding at Oakville Grill & Cellar

As a Chicago wedding photographer, I absolutely love when a wedding day becomes an adventure through the city… And sometimes, love deserves a redo.

Hannah and Bobby originally said “I do” two years ago in Florida, surrounded by all the excitement and anticipation that comes with a wedding day. Unfortunately, Mother Nature had other plans. A tropical storm rolled in and brought an incredible amount of rain to their special day, leaving them wishing they could experience the celebration they had always envisioned.

So, two years later, they decided to do exactly that.

This time, they brought their celebration to Chicago — and their second wedding day was every bit as unforgettable as they deserved. 🤍

Getting Ready at the Royal Sonesta Chicago

The day began at the Royal Sonesta Chicago, where Hannah and Bobby got ready surrounded by their closest friends and family.

There was something so special about getting to photograph these two knowing that this wasn’t simply another wedding day. It was a chance to celebrate their marriage all over again, but this time without the storm clouds hanging over the day.

Once everyone was ready, we headed out into the city.

A Chicago Adventure

One of my favorite parts of their day was that we didn’t rush from one location to the next. Instead, we walked our way around Chicago, taking in the city and stopping along the way for photos.

There is just something about Chicago that makes the perfect backdrop for a wedding day. The architecture, the streets, the energy, the little moments that happen as you wander from one place to another — it all becomes part of the story.

And Hannah and Bobby embraced every second of it.

Their wedding day felt less like a perfectly planned itinerary and more like an adventure through the city with the people they love most.

Eventually, we made our way to Oakville Grill & Cellar, where the reception was waiting.

A Reception That Knew How to Party

If there’s one thing I can say about the Schiavones, it’s this:

They know how to party. 😂🥂

The reception at Oakville Grill & Cellar was filled with incredible food, music, dancing, and a whole lot of celebrating.

They had a live saxophone player adding to the energy throughout the evening, along with one of the best DJs who kept the dance floor packed. It was the kind of reception where you could feel just how excited everyone was to be there celebrating Hannah and Bobby.

And then came dessert.

But this wasn’t your typical wedding dessert table.

The Cannoli Boys came out to entertain the guests, serving up cannoli and turning dessert into an entire experience. It was such a fun and unexpected touch — and honestly, exactly the kind of detail that made their celebration feel so uniquely them.

A Wedding Day Worth the Wait

After everything Hannah and Bobby had experienced with their original wedding day, watching them finally get the celebration they deserved was incredibly special.

This wasn’t about replacing their Florida wedding or pretending those memories didn’t happen. It was about creating another day to celebrate their marriage — one filled with laughter, happy tears, Chicago adventures, incredible food, live music, dancing, cannoli, and the people who mean the most to them.

And I think their second wedding day proved something pretty important: sometimes the redo is even better than the original. 🤍

Hannah and Bobby, thank you for allowing me to be part of such a meaningful celebration. From getting ready at the Royal Sonesta to wandering through Chicago and ending the night dancing at Oakville Grill & Cellar, your day was an absolute joy to photograph.

Cheers to the Schiavones — and to many, many more years of celebrating your love. 🥂

Planning a Chicago Wedding?

If you’re planning a wedding in Chicago, I’d love to document all of the little moments that make your day uniquely yours. From getting ready in a downtown hotel to exploring the city for portraits and celebrating with your favorite people, your wedding day deserves to be documented as the full story it is. Contact me here!