
Serena and Tony’s Chicago engagement session was all about keeping it simple and letting the city bring the energy.
Chicago is one of those places where you can walk a few blocks and get totally different looks. We leaned into that and built a session that felt like a real day together in the city.
Chicago sessions are perfect for couples who want a mix of iconic and candid.
You get architecture, reflections, clean lines, and that constant movement that makes photos feel alive. The city gives you texture and variety without needing props or complicated plans.
We approached this session like a city stroll.
We kept moving, stopped when the light hit just right, grabbed a few portraits, then kept going. That flow keeps everything relaxed and helps the photos feel natural instead of overly posed.
Serena and Tony were comfortable together from the start, and the candid moments came out constantly in between the portraits.
Chicago gives you built-in variety.
You can get classic city portraits, quieter tucked-away corners, and bold architectural backdrops all in one session. We made sure to capture a mix of wider shots that show off the city and closer portraits that keep the focus on Serena and Tony.
1) Wear shoes you can walk in.
City sessions move best when you’re comfortable.
2) Keep outfits clean and intentional.
Solid colors and simple layers photograph beautifully against busy city backgrounds.
3) Build in a little flexibility.
Chicago is unpredictable in the best way. Great photos happen when you’re open to the moment.
If you want engagement photos that feel modern, relaxed, and true to you, Chicago is a killer place to do it.
We’ll help you plan the flow, guide you through everything, and capture photos that feel like a real day together in the city.
Getting Married? Check out our work here and contact us!
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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