The Chicago Landmarks Quest: A Postmortem

As mentioned previously, in April 2009, I successfully identified an obsession that appealed to my admittedly quirky definition of enjoyable ways to spend a day. Looking back now, I was already well into this effort by the time I posted about it here. The first of my little landmark treks was all the way back on March 21st. Sadly, like so many of my 'great' ideas, this one never quite came all the way through to completion. Of course, I kept obscenely detailed records of the walks that I did take. As such, I can report lots of fun facts and statistics, such as:

• I made 13 dedicated trips to see landmarks. All told, I covered 151.8 miles of Chicago streets.
• I walked 92.6 miles and biked 59.2 miles.
• On these walks, I found $1.23 in lost change, a random key, and an Indianapolis restroom token.
• On these walks, I made it to exactly 100 of the 277 landmarks (36.1%!)
• I made this cool Google map of all the landmarks, including those I didn't make it to.

View Chicago's Historic Landmark Structures in a larger map


Beyond the numbers, I got to see a lot of interesting buildings. The variety of buildings that at landmarked in Chicago really astounds. Some sites were the location of historic events or homes of important figures, while others were selected solely for their contribution to the field of Architecture. Every time I went out with a list of landmarks in my Moleskine, I knew that I could expect to see something new in the same old city. The list took me to great neighborhoods and awful ones. It led me to places I certainly never would have visited otherwise, and gave my days a structure and goal.

A typical walk. 10.2 miles, eight landmarks, and I found 26 cents along the way.

I'd take a look at a map, pick a general direction to go in, make a list of landmarks I thought I could get to and go. Never a set route, never a timeline. The only goal was to see as many as I could and snap a picture of each, and a couple along the way. Once home I'd cross them off the map and record the route I ended up taking on Gmaps-Pedometer. In retrospect, I wish that I'd taken more note of each trip, beyond the routes and the pictures. Some stories from those trips I'll remember forever, but some I'm sure I've lost.