Holiday PopUp Portraits (Outdoors)
with Photo Session & Product Giveaways!

I’m sure we can all agree that this has been one heck of a year and 2021 just has to be better right? In the spirit of keeping us all home and safe, But if we’re all home, how will anyone see us? They say a picture is worth a thousand words, well let’s show them what words you’re trying to portray.

Put your creative hats on!  I’m launching my Holiday Popup Portraits throughout the Chicagoland area so that you don’t have to go too far and they are all OUTDOORS. I”ll have a few different backdrop concepts from Holiday Vintage Vibe to Chicago Iconic and then practically anywhere you think is representative of your family. 

All Holiday PopUp Sessions are by appointment only and are $349 and include a proofing gallery for you to choose your included 10 digital images. Custom Popup sessions are at a location of your choice are longer in session and include 15 images. Select any below for more info and to sign up.


– $50 for same day in front of your residence after outdoor sessions close
– $50 per additional photo
– 50 Flat Holiday Cards $150 (+60 for 100) with a curated collection of templates to choose from
– A Selection of wall print products

Covid Safety: I will be masked the full time and will instruct you from afar on how to pose. Practicing safe social distancing at all times…

Holiday Card Templates

Below are some of my favorite Holiday card templates provided by my vendor.

For a slightly humorous twist, the cards below are ones I’ve designed that make light of 2020. 

But Anna, what about the Free Giveaways?

I am raffling off my most popular wall print and session!!!

  1. 16×20 Metal Wall Print (retail $450)
  2. Free headshot session at Anna Cillan Photography in Chicago (retail $300) 

When you book a PopUp session, you earn one entry. After that, every referral booked through you will earn you one additional entry.  Entries open 11/17-12/31 @11:59pm. Winner will be drawn on Jan 1, 2021. Enter often….Good luck!

“made me completely comfortable and kept me laughing the whole time”

Anna was an absolute joy to work with, made me completely comfortable and kept me laughing the whole time. As for the pictures, they completely blew my mind! She is talented beyond belief and I would absolutely recommend her for any of your photography needs. Incredible work.
Anna Murphy - Chicago Muralist
Chicago based Artist/Muralist

I’m a Chicago based Headshot
and Portrait Photographer 

originally from the Pacific NW starting my professional career in computer programming moving into Testing financial software and capping off my IT career with Project Management for software implementations.  It wasn’t until a major layoff back in 2016 that jump started my journey back into the world of photography and so happy I did!  I specialize in High-End Corporate and Acting Headshots most notably used for LinkedIn and performer portfolios for Musical Theater, Acting, Modeling, and Dance.

I’ve had the privilege to train 

under the direction of world-renowned educators Scott Robert Lim, JB Sallee and am a verified member of world-class Headshot Educator Peter Hurley’s Headshot Crew. I’ve been published in the April 2019 edition of Shutter Magazine, one of the leading professional photography Magazines to date!


and don’t you forget it.  I would love for the opportunity to direct and capture you being the most authentic version of you.  I know the lights and camera gear can be intimidating, but never fear, it’s just me, a friend that may make you share in a few belly laughs throughout your session.

Oh did I say that I can sing too?  How well you ask?  That’s for me to know and you to find out.

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