Chicago has always held a special place in my heart.

Growing up nearby, I spent plenty of time visiting the city, and over the years it became one of the places that shaped my appreciation for architecture, thoughtful design, and neighborhoods full of character. This trip was a little different, though. While we were primarily in Chicago to visit my family, we also carved out time to explore the city together—and seeing it through Matlock’s eyes made me appreciate it even more.

It was also a meaningful family trip. Most of my family hadn’t seen Matlock since 2018, so it was incredibly special to spend time together. We also got to meet up with my dad, visit one of my college best friends (who was meeting Matlock for the first time!), and enjoy a slower pace than we usually do when we travel.

As photographers, we’re always paying attention to the little details that make a place feel unique. Whether it’s the way light falls across a historic building, the feeling of a neighborhood street, or the small moments happening around us, we’re constantly looking for the stories hidden in everyday places. It’s the same perspective we bring into our wedding photography experience—creating images that feel intentional, emotional, and true to the people and places we’re documenting. Chicago is full of those moments if you slow down enough to notice them.

Why We Loved Staying in the Gold Coast

If you’re planning a trip to Chicago, my biggest recommendation is to stay in the Gold Coast.

While downtown is iconic—and definitely worth visiting—the Gold Coast has a completely different personality. It’s elegant without feeling stuffy, lively without feeling overwhelming, and incredibly walkable.

The neighborhood is filled with beautiful historic walk-ups, tree-lined sidewalks, charming courtyards, and little parks where locals gather with their dogs. There were so many streets that felt like they belonged in a romantic comedy. Even though you’re surrounded by one of America’s largest cities, the neighborhood somehow feels comfortable and lived-in.

One of my favorite parts of every morning was simply walking through the neighborhood with coffee in hand before the city fully woke up.

It’s also incredibly convenient. You’re close enough to walk to many of Chicago’s biggest attractions, but at the end of the day, you get to come back to a neighborhood that feels quieter and more residential.

Our Favorite Coffee Shop in Chicago

We’re admittedly coffee snobs.

Whenever we travel, finding a coffee shop we genuinely love almost becomes its own adventure.

Out of every café we visited, DialTone Coffee & Wine Bar in Old Town was easily our favorite.

The coffee immediately reminded us of one of our favorite local cafés back home in Florida, which made it feel familiar in the best way possible. Great espresso, a welcoming atmosphere, and exactly the kind of place we’d happily become regulars if we lived nearby.

If you’re someone who plans your mornings around coffee like we do, this one is absolutely worth visiting.

The Burger That Completely Surprised Us

Our first evening in Chicago, we weren’t looking for anything fancy.

We had flown in earlier that day, walked what felt like miles, and just wanted a casual dinner before calling it a night.

We stumbled into Small Cheval almost by accident.

After the first bite, we immediately understood why so many people recommend it.

The burgers were incredible, the sauce was ridiculously good, and by the time we finished, we looked at each other and decided to order a third burger just to split because neither of us wanted the meal to end.

Sometimes the best travel memories aren’t the reservations you planned months in advance—they’re the places you accidentally discover.

The Architecture Boat Tour Was Worth Every Minute

If I could recommend only one classic Chicago activity, it would absolutely be the architecture boat tour.

My dad and I used to do things like this together when I was younger for Father’s Day, so getting to experience it again with him—and with Matlock—made it even more meaningful.

Beyond the family memories, it’s one of the best ways to understand Chicago.

You don’t just admire the skyline—you learn why the buildings look the way they do, how the city developed after the Great Chicago Fire, and how architecture continues to shape Chicago today.

By the end of the tour, you feel like you understand the city on a much deeper level.

As photographers, we loved hearing the stories behind buildings we’d otherwise just admire from the street.

 

Restoration Hardware Completely Inspired Us

Without question, one of our favorite discoveries was Restoration Hardware Chicago and the 3 Arts Club.

I knew there was a showroom, but I wasn’t prepared for just how inspiring the entire building would be.

Inside, you’ll find:

• A beautiful restaurant
• A coffee bar
• Multiple floors of thoughtfully designed showrooms
• Rooftop seating overlooking the city

One afternoon we grabbed coffee and took our laptops to the rooftop. Surprisingly, almost no one else was there, so we spent a couple of hours working while enjoying the city views surrounded by Restoration Hardware furniture.

The next day we came back for dinner at the restaurant.

It reminded us a lot of Oxford Exchange back home in Tampa—but on an even grander scale.

Afterward, we wandered through all three showroom floors, taking photos of creative design ideas and saving inspiration for our own home. Every room felt intentionally designed, and it was impossible not to leave feeling creatively energized.

If you love interior design, architecture, or beautifully curated spaces, don’t skip this stop.

Looking at Chicago Through a Photographer’s Eyes

One thing I love about Chicago is that it rewards people who slow down.

Some of my favorite moments weren’t at famous landmarks.

They were walking quiet residential streets in the Gold Coast, noticing the texture of old brick buildings, watching sunlight filter through tree-lined sidewalks, and finding little architectural details tucked into historic buildings.

I also love how dramatically the atmosphere changes from one neighborhood to another.

Walking from the Gold Coast toward Rush Street feels completely different than spending time downtown. The neighborhoods each have their own personality, and exploring them is part of what makes Chicago feel so special.

One of my favorite architectural details is the Tribune Tower, where pieces of famous landmarks from around the world are embedded into the exterior of the building. You can literally touch fragments of history from places across the globe.

As someone who appreciates both photography and design, those are the moments that stay with me far longer than checking another attraction off a list.

Other Chicago Neighborhoods We Love

If you have extra time, these neighborhoods are all worth exploring:

• Gold Coast
• Old Town
• Lincoln Park
• Lakeview
• River North
• Wicker Park

Each has its own personality, and wandering through different neighborhoods became one of our favorite parts of the trip.

A Few More Places Worth Visiting

If it’s your first time in Chicago, I’d still recommend spending time downtown.

Some of my favorite spots include:

• Millennium Park (and, of course, Cloud Gate—better known as “The Bean”)
• The Starbucks Reserve Roastery
• The Chicago Athletic Association rooftop
• The Chicago Riverwalk
• One of Chicago’s incredible museums if your schedule allows

Even if you don’t have a strict itinerary, Chicago is one of those cities where simply walking often leads you somewhere memorable.

Getting Around Chicago

One thing we’ve learned after multiple trips is that Chicago is an incredibly walkable city.

You’ll likely walk much more than you expect—which is one of the best ways to experience it—but there will definitely be times when you’ll want a ride across town.

Instead of using Uber, I’d recommend downloading the Curb app.

It connects you with licensed Chicago taxis, and during our trip it was often less expensive than Uber while being just as convenient.

Final Thoughts

This trip reminded me why Chicago continues to be one of my favorite cities.

Yes, the skyline is beautiful.

Yes, the architecture is world-famous.

But what keeps drawing me back are the neighborhoods that feel lived in, the coffee shops where you want to linger a little longer, the restaurants you accidentally discover, and the moments spent with people you love.

Sharing all of that with Matlock—while reconnecting with my family, spending time with my dad, and catching up with one of my oldest friends—made this trip even more meaningful.

If you visit Chicago, my advice is simple: don’t rush.

Walk a little slower, look up more often, wander through neighborhoods beyond downtown, and let the city surprise you.

Some of our favorite memories came from doing exactly that.