Chicago Engagement Session Locations

If you’re searching for the best Chicago engagement session locations, Maddie and Andrew’s session is the perfect example of how to turn your photos into a full experience! It’s not just a quick shoot. Instead of cramming everything into one time slot, we split their session into sunset and sunrise, giving them a gallery that feels layered, intentional, and completely unique to Chicago.

Sunset Engagement Session in Chicago

We started their session in the evening, hitting some of the most iconic and visually dynamic spots in the city.

Wells Street Bridge

The Wells Street Bridge on LaSalle is one of the best Chicago engagement session locations if you want:

• Classic city architecture
• River views
• Movement from cars, trains, and people

It gives you that unmistakable Chicago energy while still allowing for intimate moments.

Adler Planetarium

From there, we headed to Adler Planetarium—arguably one of the most iconic skyline views in Chicago.

This location is perfect for:

• Wide-open skyline shots
• Golden hour glow over the lake
• A more cinematic, expansive feel

As the sun sets behind the skyline, the light wraps around the buildings and creates that dreamy, soft look that photographs beautifully.

Chicago Theatre

We ended the night at the Chicago Theatre, which brings a completely different vibe.

• Bold, iconic marquee
• Downtown energy
• Slightly editorial, city-at-night feel

This is where things start to feel a little more elevated and stylized—like you’re stepping into a movie scene.

Why You Should Split Your Engagement Session (Sunset + Sunrise)

Maddie and Andrew didn’t stop at sunset—they came back the next morning for sunrise, and this is where the magic really stacked. We met at 6:30am the next morning to get a whole different view of Chicago!

Splitting your session gives you:

• Different lighting conditions
• Fewer crowds in the morning
• More variety in your gallery
• A more relaxed experience overall

It’s one of the best ways to maximize your engagement session.

Sunrise Engagement Session in Chicago

The next morning, we leaned into early light and quieter streets for a completely different feel.

Chicago Board of Trade

The Chicago Board of Trade building is one of the most recognizable buildings in Chicago! Going during sunrise allows us to literally dance in the middle of the street without anyone around! The lighting is stunning and we never wanted to leave!

• Strong architectural lines
• Symmetry and depth
• That classic “Chicago” street perspective

At sunrise, it’s significantly less crowded, which allows for cleaner, more intentional images.

Route 66 Sign

We wrap the session at the Route 66 sign! It’s an iconic and slightly playful Chicago landmark.

This spot adds:

• Personality
• A sense of place
• A more casual, storytelling moment

It’s a perfect way to end a session with something that feels a little less formal and more “you.”

Final Thoughts: Chicago Engagement Session Locations

Maddie and Andrew’s session is proof that the best Chicago engagement session locations aren’t just about where you go, they’re about how you experience them.

By combining sunset and sunrise, iconic landmarks and quieter streets, their session felt like a full story instead of a single moment.

And that’s ultimately the goal.

Not just photos, but something that actually feels like your time together in the city.