Over the years I have come to especially enjoy short trips to visit friends and family. These brief sojourns often turn out to be pauses that refresh, wonderful little mini-vacations. Such was the case over the weekend with a quick trip to Chicago.
On Friday, however, it appeared that this particular visit might never get off the ground. An unhappy worker allegedly set fire to the Air Traffic Control Center near O’Hare Airport, crippling the nation’s passenger aviation system. After my flight was cancelled, I was able to grab the last seat on the only JetBlue flight going from Boston to Chicago that day, arriving late at night.
By Saturday morning I was at my friends Don and Sharon’s condo in downtown Chicago, enjoying breakfast with them, their youngest son Thomas (a newly minted Eagle Scout — congrats Thomas!), and long-time friends Kathy and Rachelle. Don, Kathy, Rachelle, and I went to college together, including a memorable semester abroad in England, and Sharon has patiently endured our reminiscences for decades.
Properly fortified, we explored the downtown area, starting with a terrific boat tour on the Chicago River, replete with a very knowledgeable docent who shared stories about the city’s remarkable architecture.
The tour featured lots of memorable vistas. Chicago has long been famous for its architectural history and variety, and over the past few decades its skyline has become truly spectacular.
After more sightseeing, some shopping, and a lot of healthy walking, we finished our day with a fine dinner at a downtown restaurant.
Sunday started with a short walk around Chicago’s Millennium Park, including a pitstop at the very cool bean sculpture.
Our socializing concluded with a visit to a favorite childhood destination, Chicago’s Museum of Science and Industry. I was delighted to see that its famous model train display — my absolute favorite exhibit as a kid — had undergone a thorough upgrade.
And speaking of trains, here’s the real deal, the famous Pioneer Zephyr, which during the 1930s epitomized modern train travel.
The history geek in me loved checking out the U-505, a German submarine captured by the Americans during the Second World War. There’s an exciting story behind its capture, which you can read about here. The WWII theme of our visit also included a very well done OmniMax film about D-Day.
A side benefit of our museum visit was that I missed the Chicago Bears blowout loss to the Green Bay Packers at nearly Soldier Field. However, later that afternoon, a lot of Bears fans, dressed in their team jerseys, milled about the streets, looking understandably morose.
For dinner, I met up with my brother Jeff, who lives in nearby Glen Ellyn, Illinois, for a deep dish pizza at Medici’s, a popular eatery in Chicago’s Hyde Park neighborhood. Jeff also happens to be a wizard at computers, and he gave me some good advice on how to upgrade my Internet security practices. The pizza was pretty excellent too.

My brother Jeff, polishing off a slice of deep dish pizza at Medici’s in Hyde Park, Chicago (Photo: DY, 2014)
In addition to greatly enjoying the company of my friends and brother, what struck me was the way in which Chicago has become a world-class city, in its very own big and brawny sort of way. When I spent a summer there working for a large law firm in 1984 (here’s the story of that time!), Chicago seemed old and tired. Today, although the city certainly faces its share of challenges, its downtown feels vibrant and alive.
Among American cities, Frank Sinatra performed signature anthems about only two of them, New York and Chicago. Here’s his “Chicago,” as no one else can sing it:
And, Chicago was thrilled that you came! The sky was at its best wearing cobalt blue. The sun was twinkling down on the skyscrapers leaving sparkles on the buildings. Even the Chicago River was shining! Come back anytime! There is always a new adventure in Chicago. Sharon
Thank you, Sharon, it was a great visit!