Where to Take Engagement Photos in Chicago with Skyline Views

When people imagine photos with the Chicago skyline, they often picture the city glowing behind them at sunset. And yes — that is just as magical in real life as it sounds. But there’s one little detail that’s easy to miss if you’re new to Chicago (or just haven’t paid attention to where the sun actually sets): the sun goes down behind the city, not over the water. 

So while you won’t get a golden sun sinking into the lake, you will get a soft, warm, glowing sky behind the buildings — and that creates a very cinematic look. Especially in summer and early fall. 

Here are two locations that always deliver that view beautifully: 

1. Milton Lee Olive Park

Tucked just behind Navy Pier, Milton Lee Olive Park feels like a quiet pocket in the middle of the city. You get that amazing open skyline view — downtown rising right in front of you — but the atmosphere is surprisingly calm. There’s water, trees, open pathways, and enough space to move around without feeling crowded. 

I’ve photographed here multiple times in the evening, and even if there are people around, it never feels overwhelming. You can always wait for a moment when the background clears and capture those clean, intimate frames. The light here at sunset is soft and flattering — the city becomes this gentle silhouette behind you, which works beautifully for romantic portraits. This spot is great if you want something close to downtown, but still a bit serene. Think: hand-in-hand walk, quiet moments, some laughter — and the skyline just there, effortless and iconic. 

2. North Avenue Beach Pier

 This is the classic Chicago city-view shot — bold, wide, and unmistakably “Chicago.” The pier gives you that long open angle across the lake, so the skyline looks tall and panoramic. It’s one of those places where you see people stop mid-walk because the view is that good. 

Yes, it can be a little busier, especially on warm evenings — but don’t worry. I’ve done several shoots here around sunset, and there’s always a rhythm to the crowd. People come and go, and with just a bit of patience (or shifting a few steps to the left or right), you can catch moments where it’s just you, the water, and the skyline. I help direct so you don’t even have to think about it. 

The vibe here is slightly more energetic than Olive Park — more “city life by the lake” — but that energy can be beautiful in photos. Wind in your hair, the lake moving behind you, Chicago glowing just above.

So, which one should you choose?

Both are perfect around sunset — just remember, the light comes from behind the buildings, creating soft ambient glow instead of bright golden rays across the lake. If you love a clean city silhouette and warm pastel tones in the sky, that’s exactly what you’ll get.