Capturing Life's Moments with Chicago Lifestyle Photographer

More About Me:

My name is Jesse Leon, and I’m originally from Woodstock, Illinois. Growing up, I always loved movies, but I never imagined becoming a filmmaker myself. That changed during my sophomore year of high school when I took a multimedia production class and discovered my passion for working with cameras. I loved filming as a way to document the world around me.

Through both filmmaking and photography, I’ve learned the importance of capturing the moments that define our lives—the celebrations, the milestones, the love we share. These memories, preserved through a photograph or a film, can live on forever. That’s what draws me so deeply to these art forms: their power to tell human stories and preserve them for generations to come.

My style focuses primarily on natural light and lifestyle-driven imagery rather than traditional studio work. I aim to create authentic, dynamic portraits that feel both polished and natural. Doing portraits outdoors not only gives us more space to work with and have a variety in backgrounds for photos/videos, but also allows us to get comfortable and not be intimidated by big setups.

HOW I WORK:

I operate on a day-rate pricing model rather than offering fixed packages. While many photographers and videographers create packages for specific types of events, I’ve found that a flexible day-rate structure works better for both me and my clients.

I don’t separate pricing for photography and videography sessions. Whether you book me for a one-hour photo session or a one-hour video session, the rate is the same. This keeps things simple and avoids unnecessary complexity.

My half-day rate covers 1 to 6 hours and typically ranges from $350 to $600, depending on how many hours I’m booked for. Full-day rates apply to 8 or more hours and range from $650 to $800.

Example:

If a client books a one-hour portrait session, the rate is $350 regardless of the type of session—whether it’s a solo shoot, family session, or engagement.

Solo sessions typically include 60+ high-quality edited images that clients can use for social media or personal portfolios. Family and engagement sessions usually receive 120+ edited images due to the variety of groupings and moments captured.

For weddings and longer events, clients can expect 300+ edited images, depending on the length and scope of the event. If you would like to talk more about the event you would want to get coverage for, please contact me through the contact page and we can discuss more about working together and how many photos will be in the final gallery. Booking is also done through the contact page!