Downtown Chicago Engagement Photos at Pendry Chicago & outside The Wrigley Building

I’m always a sucker for an engagement session in the city. Between the architecture, the movement on Michigan Avenue, and the sparkle on the Chicago River in the morning, it all creates a setting that feels both cinematic and timeless.

For this Downtown Chicago engagement session, we began inside the elegant Pendry Chicago before stepping out into the city for portraits overlooking the Chicago River by The Wrigley Building. The combination of refined interiors and sweeping skyline views created the perfect setting for Maria & Ryan’s engagement photos. The vision was flashy, stylish, romantic – all ideal for downtown Chicago.

Engagement Photos at Pendry Chicago

Starting inside the Pendry, we began in the bar area before moving into the stunning lobby space.

Located along Michigan Avenue in the historic Carbide & Carbon Building, Pendry Chicago blends Art Deco architecture with modern luxury design. The interiors are warm, elegant, and full of beautiful textures — making it one of my favorite spots for engagement photos in downtown Chicago.

With this session being right in the middle of winter, starting this engagement session indoors created a relaxed, intimate atmosphere that feels a bit like a date day. The soft lighting, cozy seating areas, and refined design allowed us to capture natural moments between them before heading outside into the cold energy of the city.

For couples who love a mix of editorial elegance and candid moments, locations like Pendry Chicago create the perfect backdrop.

Film Engagement Photos at The Wrigley Building outlook

Some of my favorite images from this Chicago engagement session were the film photos we captured along the river next to The Wrigley Building.

With the sun beating down on us, and me shooting with Portra 800, I was initially nervous these would come out too bright, not thinking about just how light hungry film really is. But the minute these scans from Goodman Film Lab hit my inbox, I fell completely in love. The grain, softness, and color that Portra 800 produces add a rich, nostalgic quality that pairs beautifully with the architecture and water reflections along the Chicago River.

I always love how film invites a slower pace to each session. It encourages couples to simply be present with each other while I capture moments that feel genuine and timeless. And with the skyline rising behind them and the early afternoon light reflecting off the river, these film frames quickly became some of my favorite photographs from the entire session.

Why I Love Photographing Engagement Sessions in Downtown Chicago

As a Midwest based photographer, I’m always inspired by the energy of this city.

Downtown Chicago engagement sessions offer an incredible variety of backdrops within a small area — elegant hotels like Pendry Chicago, iconic bridges along the Chicago River, historic architecture, beautiful gardens in the summer, and vibrant city streets that create a sense of movement and excitement.

For couples who love the energy of the city, Chicago engagement photos create a gallery that feels both editorial and deeply personal.

Mikayla Scheibe Photography | Chicago Editorial Wedding Photographer

Planning Your Chicago Engagement Session

If you’re dreaming of engagement photos in Chicago, there’s truly nothing like the energy of downtown. Every corner offers something a little different, which is what makes sessions here feel so dynamic and personal.

If you’re planning a Chicago wedding or simply want engagement photos that feel elevated, romantic, and true to you, I would absolutely love to document it for you.

Inquire with me to start planning your Chicago engagement session or wedding day — I can’t wait to hear what you’re dreaming up!