Consider me lucky. A couple weeks ago I was in Chicago for Lost Type’s annual field trip. My buddy and founder of Lost Type, Mr. Riley Cran, has been inviting me to go on their annual trips for over three years now, so I knew had to attend this one, or else no more trips… Here’s a little recap of my glorious adventure.

I caught a red-eye to Chicago, got in a day earlier than everyone else, and wanted to explore around. I’ve never been to Chicago before, so everything was a new experience. I wasn’t prepared for how big the city actually is. I was constantly looking up, amazed with every building, every detail. I was getting strange looks along the way, but thought why isn’t everyone looking at these amazing structures?

My wife Tess has been to Chicago before and said you must go on the river architectural tour in order to get some backstory on all of these buildings. While waiting for the tour, I checked out this painstakingly created model of (mostly) every downtown building. There was also this intense infographic map that categorized every building, when it was built, etc., by color.

Here are some pics of buildings on my way towards the tour. Just simply amazing that so many buildings were created in such short periods of time. I loved the elevated trains and the structures that hold them. I seen them so many times in movies, but it was a real treat to see them in real life.

And now, on to the tour. I believe I was on the Classic Lady boat for the tour, with a knowledgable tour guide, who is a therapist by day, and he volunteered his time on the weekends for these tours. This is his therapy. He spoke of Trump’s in-your-face signage, Marina City’s city within a city, Mercantile Market, Wrigley building, and countless other buildings and defunct draw bridges, etc. I had no idea that the city switched the river’s flow in order to save the city’s water supply in the early 1900’s.

The tour took us out near Lake Michigan’s locks, where we learned a brief history of George Washington Gale Ferris, Jr.’s original design of the Chicago Ferris Wheel in 1893. It was the centerpiece of the 1893 World’s Columbian Exposition in Chicago.

After that history lesson, it was back to the dock, and time to check into the hotel. My wife surprised me with an executive suite in the historic Palmer House Hotel. This hotel is amazing and contains the famous Peacock doors and exquisite and ornate lobby.

I couldn’t find the 28th floor in the elevator bay, come to find out, I had a special elevator, complete with leather-bound chair. Man, this place was spacious. I felt guilty to be the only one sleeping in such a huge room, but only briefly, as the red-eye finally took its toll. Out for the night, but return here tuned for more adventures soon.