Why Working With a Photographer in Chicago Shouldn’t Be Complicated
- Omar de Jesus Landaverry Huitz
- Oct 1, 2025
- 3 min read
If there’s one thing I’ve noticed in this industry, it’s that people often come to me with a bit of hesitation. Not because they don’t want their photos taken—they do! But because, honestly, working with photographers can feel… difficult. When people search for a photographer in Chicago, they’re often excited about the photos they’ll get—but nervous about the process that comes with it.
I’ve heard the stories: confusing contracts, complicated payment methods, and photographers who feel more like distant observers than true partners. That doesn’t sound fun, right? It feels like work before the work even begins. That’s not how I work! My approach is simple: I want to be your partner, not just the person holding the camera.
If it’s an engagement photoshoot in Chicago, I’m not just quietly clicking away — I’m celebrating that “yes” with you. I’ll laugh with you, cheer with you, and capture the raw emotion that makes that day unforgettable. If it’s a corporate headshot session, I want you to look approachable, confident, and authentic. I ask myself: “Would I hire this person if I saw this photo on LinkedIn?” That’s the bar I set for myself and for you.
While booking a photographer in Chicago, simplicity works better
One of the things I’ve committed to is making everything as simple as possible:
Payments: straightforward, with flexible options (Zelle, CashApp, or card if needed).
Contracts: clear and easy to read. I don’t believe in fine print that makes you feel tricked.
Process: you know what to expect from the start, from booking to delivery
When you decide to book a photoshoot, everything is automated. Contract sending, invoices, payments, and delivery. When the logistics are simple, you get to focus on what really matters — enjoying your experience and looking your best.
Real Experiences, Real People
I’ve had clients tell me after their sessions, “This was way easier than I thought it would be.” That’s exactly the feedback I want.
For example, Kyle came to me nervous about his engagement session. He was proposing at the Nature Boardwalk at Lincoln Park [one of my favorite spots on my list!], and it was a surprise photoshoot! Kyle was worried about me being incognito and the fact that he thought maybe he wouldn't find me around the place.
This is why I love working with clients as their partner. In an ideal setting, Kyle and I would've met beforehand and planned every detail beforehand, but that was not this particular instance. I shared my live location, told Kyle how I was dressed (I always try to wear a black shirt with my name on it!), and asked him to share how they'd be dressed. Once we saw each other, we gave each other a little nod, and that triggered everything to start. Kyle & Brooke's proposal photos were stellar!
After the big question, they were worried it would feel staged or awkward, because they are not used to taking pictures of themselves. That's what I was there for! Within minutes, we were joking around, and by the end, they said it felt like hanging out with a friend who just happened to have a camera. The photos? Natural, emotional, and very them.
I also worked with a company here in Chicago that needed team headshots but dreaded the “stiff corporate” vibe. We set up a relaxed shoot, had music playing, and cracked a few jokes between shots; it was also shot in their office, so they felt used to the place where the pictures were taken, around friends they see every day, who were around to make sure they had a genuine smile and were laughing around. They ended up with portraits that looked professional but still approachable, and their whole team told me it felt like a team-building event instead of a chore. This also happens with realtors! They are left hanging with a very common question: What do I do with my hands? How do I pose?
That's what I am here for, too!
Why collaboration matters
Photography isn’t just about angles and lighting—it’s about connection. You’re not hiring someone to stand silently in the corner and click away. You’re inviting someone to capture moments that matter, whether it’s a personal milestone or a brand you’ve built from scratch.
When we work together, I want you to feel like we’re on the same team. That’s the difference between photos that just look good and photos that feel real.
If you’re looking for a photographer in Chicago who believes in simplicity, collaboration, and celebrating alongside you—I’d love to be that person.
📸 Ready to book your session? Click here to schedule your shoot! I recommend booking 2–3 weeks in advance to secure your spot.































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