I was recently in Chicago for DynamicsCon, a top-tier community event for users and implementers of Microsoft’s Dynamics platform–Like Me!
The conference was an excellent chance to catch-up with old friends, make new ones, and learn about the latest happenings in the world of Dynamics (If you’re curious, there are a lot of happenings).
DynamicsCon was also an opportunity to learn about Chicago.
I took in a Cubs game at Wrigley with some friends.

(Justin Turner hit a walk-off RBI for the win over the Marlins)
I also dropped in to train jiu jitsu at a local place.

(Serafin Jiu Jitsu is the most beautiful gym I’ve ever visited)
My Uber driver suggested the best way to learn about Chicago is to take an architecture boat tour–boats ferry you around the Chicago river and they tell you about the buildings. I didn’t have time for a boat tour, but his recommendation primed me to think about the architecture and design of the Chicago skyline. As I walked around Chicago, I snapped pictures of buildings that interested me.
Problem: I didn’t have an architectural tour guide to tell me about what I was seeing.
Solution: I built one.
–INTRODUCING–
Willis: A Chicago Architectural Tour Guide

Sears Tower will ALWAYS be Sears Tower to me, but I named this bot Willis because it seemed like an appropriate cousin to Watson. Simply upload a photo of your Chicago structure and Willis will tell you a bit about what your looking at and how it came to be.
An advantage over an architectural boat tour: Willis can also go on land.
I’ve written other posts on how to create a custom GPT. If you are interested, these are Willis’ configurations:

Without further ado…
A Chicago Architectural Tour, Guided By Willis
Pictures by me (All Text by Willis):

Alright! You’ve captured some amazing shots of the Merchandise Mart—or as us locals call it, “The Mart.”
🏢 Name: The Merchandise Mart
📍 Location: 222 Merchandise Mart Plaza, Chicago, IL 60654
🗓️ Year Built: 1930, during the era of Art Deco’s peak style (think Al Capone and the start of the Great Depression!)
🎨 Notable Feature: The building’s imposing size—it covers over 4 million square feet—earned it the title of the world’s largest building when it opened. That’s like 22 football fields of floorspace!
🏆 Historical Fact: Originally owned by Marshall Field & Co., it was later bought by the Kennedy family in 1945. The Mart also played host to radio station studios in the 1930s and, more recently, has become a major hub for design showrooms and tech startups.
Fun tidbit—when the Chicago Bears last won the Super Bowl in 1985, The Mart was already well-established as a local icon!
The building overlooks the Chicago River and is known for its striking setbacks and vertical emphasis—a classic example of Art Deco style.
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