I’m not sure how Frank Sinatra actually felt about Chicago but I can tell you my feelings experiencing downtown Chicago after a recent family trip. The overall verdict: very nice!
You may not know it but I was born in the city of Chicago and lived in the near southwest side of the loop off south Damen Avenue until I was five. I remember the paralyzing snowstorm of 1967. Shortly thereafter, we moved to the southern suburbs and I spent the rest of my youth in Steger, Illinois.
Now, I know the highlights of downtown Chicago like where the museums are and the general layout. But on this trip I learned a lot about my hometown and experienced a lot of new things. I can say for the first time a quite a while that I actually miss being back at my roots.
We were in Chicago for four nights and three and a half days. We squeezed quite a bit into the trip. We vowed not to eat at a chain restaurant. There were definite things I wanted to see and each family member had a favorite. The weather was amazing; only one rain shower. We used Uber like crazy! There was by good fortune a Jazz Festival going on.
I plan to loosely document our trip in several parts. Nothing too deep. I’ll hit the highlights.
And as is the case nearly every time we return from a trip, I’ll spend an inordinate amount of time on Zillow looking to “winter” or “summer” where we just visited. That is of course until the price tags are revealed and reality sets in. A guy can dream, right?