In Photos: A Day at Digital Summit Chicago 2026

Consider this your virtual press pass to the sessions and speakers that shaped this year’s event.

Key Highlights

  • A behind‑the‑scenes look at Digital Summit Chicago, from the show floor to the sessions and every moment in between.
  • Ideas as they landed in real time, from early‑morning conversations to post‑session reflection.
  • The themes marketers kept circling back to — AI, visibility, video, audio and storytelling — captured in context.

There are a lot of ways to document a conference. You could take the influencer route and live stream/post everything and anything at the event, from the selection of sugar substitutes at the coffee bar to the presenter’s font choice for their slides. You could go full journalist — recorder running, questions ready, press badge front and center. You could play the part of the diligent student, sitting in the first row with a laptop open, furiously transcribing every slide like your life depends on it. You could be the laid-back learner who prefers to be in the moment, letting the information sink in as new ideas wash over you.

All valid. All been done.

But what I wanted from Digital Summit Chicago was something a little more personal than a thread and a little more honest than a highlight reel. I wanted to show you what I actually saw. So I charged up my iPhone, paid attention, and tried to capture the way it actually felt to be there. 

This piece was created with the help of generative AI tools and edited by our content team for clarity and accuracy.

About the Author

Alexis Gajewski

Alexis Gajewski

Contributor / AI Expert

Alexis Gajewski is the Associate Director of Newsroom Operations and Development at EndeavorB2B, where she leads editorial strategy and AI integration across a portfolio of 80+ B2B brands and 150 editors. With 18+ years in B2B media, she is best known for building the systems, training programs, and organizational infrastructure that help editorial teams operate at a higher level — faster, smarter, and with clearer standards.

Her expertise spans the full editorial stack — from SEO, GEO, and analytics to AI literacy, content strategy, and journalistic standards — with a particular focus on translating emerging technology into practical frameworks editorial teams can actually adopt. She designs and delivers training programs that meet teams where they are and build toward where the industry is going, with a specialty in AI integration that covers everything from foundational literacy to advanced workflows and agentic applications. A frequent guest on ASBPE webinars, Alexis is a recognized voice on the intersection of journalism and AI, and she writes for marketers, editors, and authors on how to thoughtfully and strategically implement AI practices.

Connect with Alexis on LinkedIn