
Katie and Andrew’s Chicago engagement session had that perfect “let’s go do our thing” energy.
We started with a walk through Humboldt Park for greenery and classic Chicago park vibes, then wrapped things up at Lucy’s for a cozy, laid-back finish that felt like a real date night.
Humboldt Park is a solid Chicago engagement session location when you want something scenic without leaving the city.
It gives you walking paths, trees, and a bunch of little pockets where the background cleans up nicely. It’s also great for couples who want a session that feels relaxed and natural, because you can just walk, talk, and stop when the light looks good.
We kept the first half of the session moving at an easy pace.
A few classic portraits, plenty of candid moments, and the kind of in-between laughs that always end up being the favorites. Humboldt Park is great for this because it doesn’t force you into one spot. We could explore a bit and let the session unfold naturally.
After the park, we headed to Lucy’s to finish the session with something more cozy and personal.
We love adding a stop like this because it instantly changes the vibe. It’s warmer, more relaxed, and it gives you photos that feel like your real life together. Drinks, a little flirting, and a moment to just hang out with some great food. That’s the good stuff.
This combo gives you variety without making the session complicated.
Humboldt Park adds natural scenery and open space. Lucy’s adds texture, mood, and that date-night feel. Together, it tells a fuller story and makes the final gallery feel more like you two, not just a pretty backdrop.
1) Pick outfits that work in both locations.
Something comfortable for walking that still feels intentional for an indoor stop.
2) Build in time for a drink break.
Ending at a bar gives you a natural way to slow down and get cozy on camera.
3) Keep it date-night simple.
You don’t need props. Just show up and be yourselves. We’ll take it from there.
If you want a session that mixes scenic city spots with your favorite hangout places, Chicago is perfect for that.
We’ll help plan the flow, keep it relaxed, and capture a gallery that feels like you two from start to finish.
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We’re Westley Leon Studios, a team of wedding photographers in South Bend, Indiana with an unwavering commitment to authentic imagery and a personal experience. For the couples who choose a damn good time over stuffy propriety every time.
Studio Address: 218 Front St Niles, MI 49120
Mailing Address: 1606 Oak St Niles MI 49120
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