
Chicago ranks with New York, Boston, and San Francisco in terms of the cities I love to visit. I have been to Illinois on three very different trips, but Illinois is synonymous with Chicago in my mind. It all started in 1978 when I made my first visit for a weeklong seminar for young prosecuting attorneys. The guy I shared an office with at the district attorney’s office and I were sent off to Chicago to learn how to prosecute cases at Northwestern University. Although the conference was sponsored by Northwestern, the group was housed at a hotel in the downtown area. The cruel irony was that our hotel was adjacent to the Playboy Bunny Club. Every time we ventured out on the street we encountered some interesting spectacle that one did not see in Bangor, Maine. The “gentlemen and ladies” alighting from the cabs were memorable. https://chibarproject.com/reviews/playboyclub/
Speaking of Bangor, I left my “boyfriend” Harold there when I embarked on this adventure, but he took a great interest in my trip. Chicago meant a lot to Harold because he had been arrested there in 1968, protesting the Vietnam War at the Democratic convention that year. Harold attended college at Elmhurst, a school in the suburbs, but he frequently traveled into the city on the train. He loved Chicago although he never traveled there with me other than to rush through the airport changing planes on our way to some other destination. That first trip to Chicago had another unusual twist in addition to Playboy Bunnies. Harold insisted that I take his credit card to cover any emergency expenses I might have. He and I had been dating for less than one year and marriage was not something we had considered, but the guy was so concerned he insisted I take his credit card. Bear in mind that in 1978 I did not have a credit card of my own which is why he insisted that I take his. Fortunately that experience convinced me that I should get a credit card for myself after I returned from the trip. Credit cards were not ubiquitous in 1978 and if I had waited until I got married, we might have had to get a joint card. Luckily I got my credit card in my own name and always kept my credit separate from his. https://www.experian.com/blogs/ask-experian/women-and-credit/ Much of the credit for the improved credit status for women goes to Ruth Bader Ginsburg. https://time.com/nextadvisor/credit-cards/ruth-bader-ginsburg-credit-card-legacy/

My second trip to Chicago was another work trip, many years later in the middle of the first decade of the 21st century. This conference was in July and Harold’s excuse was he would sooner starve to death than endure Chicago in the July heat. He was wrong. Turns out the weather was delightful that week with a strong breeze blowing off Lake Michigan every day. I took an architectural tour of the city on a riverboat, one of the most worthwhile and educational tours I have ever taken. I took the same tour when I visited Chicago in 2019 and the guide was the worst I ever had, so maybe it had been the luck of draw. Whether you get a lousy guide or a superlative one, viewing the Chicago skyline from the river is a wonderful experience. Chicago, like San Antonio, has a “riverwalk” with cafes and shops along the riverbank. The apocryphal story told by the first guide was that Mayor Daley had visited San Antonio, enjoyed the riverwalk, and came home and told the city fathers they had to build one in Chicago. In any event the Chicago River is a delightful place to stroll or cruise.


My third trip to Chicago came in the summer of 2019, after Harold’s death the prior winter. My daughter and I traveled from Seattle to Chicago on the Empire Builder, a train trip Harold and I had planned to take. This trip was my first visit to Chicago as a complete and total tourist and I loved revisiting sites and discovering new ones. My daughter had visited Chicago before (this was her second train trip across the country from the west coast). She knew how to efficiently move around the city and visit the “usual suspects.” Of course that meant the Chicago Art Institute with its iconic Grant Wood painting and the Navy Pier. Our surprise treat of this visit was that she was able to secure two great tickets to the traveling version of the Broadway hit “Hamilton” allowing us to view the production from the first row of the balcony at a fraction of the cost of a Broadway ticket. We also spent some time on the shore of Lake Michigan, one of the most magical parts of Chicago. I always find it amazing that a beautiful lake with a gorgeous sand beach is right there in the city, with its Gold Coast of luxury high rises at the foot of the Magnificent Mile. Chicago might just be your kind of town too.


Frank Sinatra captured it best. I love to hear him sing about this amazing city where Michelle and Barack Obama and Hilary Rodham Clinton all have roots. Wrigley Field means the same to them as Fenway Park means to Bostonians. I think part of what makes a city great is its relationship to its ballparks and stadiums. Too bad so many of those places have been torn down and attempts to replace them with retro-classic ballparks like Camden Yards in Baltimore have not been too successful, although Camden Yards itself is well received (by my late husband at least, who traveled there once to watch the Red Sox). Anyway, take a minute and hear Sinatra sing about my kind of town. https://www.youtube.com/watch?v=fwfEemlYqo8&t=8s