A Day of Architecture and Street Photography in Chicago

Over the past year, I’ve found a deep appreciation for the art of architecture and nature photography. Lately, I’ve been hitting the streets with no objective other than to capture unique scenes —simple, raw, and entirely from my point of view. This inspiration led to my latest adventure: taking the train from Milwaukee, Wisconsin, to the Union Station in Downtown Chicago for a full day of solo photographing.

A photo of Racine, WI Wind Turbines

A Dawn Departure and the Morning Commute

My day started bright and early at 6:00 AM as I boarded the train. My journey began instantly with an amazing train conductor, who was entirely supportive of my project, he allowed me to take his photo right there on the train platform —a perfect start for my street photography mission!

Chicago is a famously walkable city, I knew the morning would deliver a dynamic mix of "characters." I wanted to capture the hustle and bustle of the morning commute. Right after leaving Union Station, I found a fantastic diner for breakfast and managed to capture some exceptional photos of the surrounding areas as the city was waking up.

Chicago Morning Commute

After fueling up on a delicious omelet, I set off through downtown. I had wisely purchased tickets to the Art Institute of Chicago the day before, saving me from the infamous lines. Along my walk, I captured some great shots of DOT workers and paused to admire—and photograph—a cool gentleman's hat. Everyone I encountered was incredibly supportive, even offering tips on great photo spots throughout the city.

Architecture on the Water

It was during this initial walk that I spotted an advertisement for an architectural boat tour along the Chicago River. I immediately thought, Let's do it!  I bought a $45 ticket, secured a perfect spot on the back deck, and was rewarded with some of the most awe-inspiring architectural photographs I have ever taken.

The tour itself was deeply insightful, packed with city history and delivered with a palpable Chicagoan pride. It was a complete game-changer for capturing the skyline.

Art, Reflection, and the Classic Chicago Dog

After the amazing tour, I continued my urban trek. I found a quiet, stunning photo spot by the lake to simply relax and enjoy the amazing sunlight before heading to the museum.

When I finally reached the Art Institute, I made a deliberate choice: I left my camera packed away. I wanted to truly take in the experience and be present in the moment. I did, however, get a few impromptu lessons after tagging along behind a tour group (shhh!).

Hungry for more Chicago flavors, my final stop before heading home was a classic hot dog stand for a definitive Chicago dog—no ketchup, of course!

This trip was my first fully solo photography adventure, and I had an absolute blast soaking up every moment. It's proof that challenging yourself, whether you’re an artist or an adventurer, is always worth the effort.

Do you want to see a dedicated post detailing the best architecture photo spots I found on the Chicago River tour?