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Crown Point, Indiana 46307
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A Timeless Winter Engagement at the Chicago Riverwalk & Cultural Center

February 16, 2026 Steve Vansak

Downtown Chicago is the perfect spot for winter engagement photos. It provides a great backdrop in any season, but in winter it offers the chance to duck in and out of the cold when needed.

Madeline and Evan wanted some indoor architecture for their engagement photos, as well as some slice-of-life and candid outdoor photos.

We started inside the Chicago Cultural Center for some editorial photos with the wonderful building as a backdrop, then moved outside for more candid, romantic city engagement photos.

Inside, the Cultural Center exudes light and craftsmanship — a haven for Chicago engagement photographers and couples who love elegant, artistic backdrops.

The grand staircases in marble were perdect for more candid style photos. We did a few of these before a kiss inside the closing elevator had us going outside.

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The Chicago Riverwalk is one of the most versatile and visually striking locations in the city — which is exactly why it’s a favorite for many Chicago engagement photographers.

It was the perfect location for us to transfer from the editorial style photos we did indoors, to more candid engagement photos.

In a city like Chicago, black and white images feel timeless. The bold architecture, strong lines, iron bridges, and dramatic skyline naturally lend themselves to contrast and depth — elements that shine without the distraction of color.

As a Chicago engagement photographer, I love how black and white photography emphasizes emotion first. In Chicago especially, black and white doesn’t feel trendy — it feels classic, cinematic, and forever.

As dusk came upon us, our last images of the session were those of the iconic Chicago Theater, with Madeline and Evan casually crossing State Street.

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In Chicago Photography, Engagement Tags Chicago engagement session, chicago engagement photographer
January Wedding at Journeyman Distillery | Valparaiso, Indiana →

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