I have a studio I love in downtown Naperville. Hair and makeup, controlled light, a wall of backdrops, coffee. For a lot of people, that's exactly right.

And then there are the sessions where the whole point is the city.

I'm Emily Cummings, a branding and portrait photographer based in downtown Naperville, and a growing share of my work now happens on location in downtown Chicago. Here's what that actually looks like, what you walk away with, and how to decide whether it's the right call for you.

What "on location" really buys you

The obvious answer is better backdrops. That's true, but it's not the real answer.

The real answer is range. In a studio session, we change your outfit and change the backdrop. On location, we change your outfit, the backdrop, the light, the architecture, the mood, and the story, sometimes within a single city block. One recent session moved through a glass office with the skyline behind her, a room lined with books, an open rooftop, a wall of window light, a working-at-the-desk setup, and a rooftop pool. Same morning. Same client. Six completely different visual worlds.

That matters because you don't need one great photo. You need a library. A website banner that's horizontal. A LinkedIn headshot that's tight. Something vertical for stories. Something with negative space for text overlay. Something that looks like Tuesday and something that looks like a magazine. On location, we build all of it at once.

Where we shoot in Chicago

I have a working shortlist, and I add to it constantly.

The Riverwalk and the bridges, for the classic Chicago frame everyone recognizes. State Street and the Loop, for architecture that towers. Under the El tracks, where the middle of the day somehow turns golden. Rooftops, for the wide-open skyline shots that make a website homepage. Glass office interiors and lobbies, for the corner-office energy. The lakefront and the steps, for anything that needs to feel like an actual life instead of a headshot. And the quieter neighborhood streets, Fulton Market, River North side streets, West Loop alleys, when the brief calls for texture rather than skyline.

We pick from that list based on what your photos need to do, not based on what's pretty. That's the whole difference.

Who books on-location sessions

Business owners and founders who need a content library, not a headshot. Speakers and authors who need press photos with visual variety. Professionals whose brand is genuinely urban and whose studio headshot has never quite fit. People doing dating photos, where the entire goal is showing a real life in real places. Families who want the city instead of a backdrop. And seniors who want photos that don't look like everybody else's.

How we plan it

Every on-location session starts with a real conversation before we ever pick a corner. What are the photos for? Who are you trying to reach? What rooms do you want to be in a year from now? Then I build a route, usually three to five locations within a workable radius, sequenced so we're chasing good light rather than fighting it, with your outfit changes mapped to the stops.

You'll get a style guide with wardrobe direction and a rough timeline. Hair and makeup can happen at my Naperville studio before we drive in, or we can arrange it in the city. On the day, I direct every single frame. If the phrase "I'm so awkward in front of a camera" just went through your head... everyone says that. So am I. I got you.

Frequently asked questions

How long is an on-location session in Chicago? Plan on two to four hours depending on how many looks and locations you want. Time in the car and the elevator is real time, so we build the route to minimize it.

What if it rains? Rain is often better. Wet pavement reflects light, the crowds thin out, and umbrellas are a great prop. That said, we'll always have an indoor option in the route, and if the weather is genuinely unworkable we reschedule at no cost.

Do you need permits to shoot in downtown Chicago? For a small portrait session with handheld gear, the vast majority of what we do requires nothing. Some private plazas, rooftops and building interiors do require permission, and I handle that in advance so nobody gets moved along mid-session.

Is on-location more expensive than a studio session? There's a travel component, and longer sessions cost more than shorter ones. But per usable image, on-location sessions are usually the better value because of the sheer variety you walk away with.

Can I do part studio, part on location? Yes, and a lot of people do. Hair and makeup plus tight headshots at the studio in Naperville, then into the city for the environmental frames. Best of both.

Let's plan the route

If your photos have been living in one backdrop for too long, the city is right there.

Call or text 312.600.5151, or email emily@emilycummingsphotography.com. I'm based at Studio 25, 25 W. Jefferson Ave in downtown Naperville, and I shoot on location throughout downtown Chicago and on-location at Streeterville, 220 E. Illinois Street.

Warmly, Emily

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