FILED IN: Weddings, Video

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Ann Oleinik is a Chicago-area branding photographer who works with women and small business owners ready to elevate how they show up online.

Her sessions go beyond traditional headshots, creating a full suite of images—from lifestyle and behind-the-scenes content to modern, polished portraits—designed to support your website, social media, and marketing.

Known for her calm, supportive approach, Ann guides every client through styling, posing, and expression so you not only look like yourself—but like the most confident, aligned version of who you are becoming.

Hi, I'm ann

Tessa and Jake’s wedding day makes me feel like the luckiest girl in the world. The University Club of Chicago feels like a castle in the middle of the city, the day was fun and flawless thanks to Clementine Custom Events, and the details were absolutely perfect. But all of that was just icing on the cake. Tessa and Jake are just two wonderful souls – kind, caring, thoughtful, easy-going, fun – I could go on and on. It was an honor and a pleasure to spend the day with them and their families. I will remember their wedding for a long time as one of my favorites!

What can I say? I have to admit that I love these photos and I can’t wait for you all to see them. Thank you so much, Tessa and Jake, for inviting us to capture your wonderful, amazing, beautiful day! I can’t get enough of Tessa’s gorgeous Carolina Herrera dress and the thoughtful, fanciful florals by Fleur. Enjoy!

University Club of Chicago Wedding Photos