Chicago Blues: Prelude

(Continued from Blog-in-Progress (BiP): ♫Sweet Home Chicago♫)

Featured Photo: “Hotel View, S. Wabash Ave.”  Chicago, Illinois—2025

You can’t make this stuff up. When I began writing this post on the 3rd day of my trip to Chicago, I was gazing at the spectacular view of Wrigley Field—the historic, celebrated home of the Cubs—outside my 5th floor window at the Hotel Zachary.

I’d splurged for a stadium view, but I wasn’t there because of my love for baseball; it was mid-January and Spring Training hadn’t even begun. They had set up an ice rink on the field to host a couple of outdoor hockey games, but I’m not a hockey fan. Besides, it was too cold to sit outside for long; an Arctic Blast was expected overnight, with temperatures dropping to single digits. And I hadn’t come to the Windy City for my love of beer, although Chicago boasts some top-notch breweries.

I would get to spend a few days with my younger son, who’d recently moved there to begin his career after college; but visiting him was an added bonus. It was, in fact, my love of music that had carried me to Chicago. Specifically, the Blues. More specifically, a chance to see Buddy Guy, the octogenarian guitarist, play a live show at his club—fittingly named “Legends”—on South Wabash Avenue. And it all started on a whim and a chance remark.

The ball had recently dropped in Times Square to usher in 2025, and on the first Friday of the new year, I sat with a friend from Merck at our favorite watering hole.

He was recounting his recent holiday trip with his son and daughter to Vienna, and said that along the way he began making plans for his 65th birthday in January. He’d shared one outlandish possibility with his kids, and they urged him to just do it. So, he’d booked a flight to Chicago, made a hotel reservation, and bought a Standing Room Only ticket to see the show at Legends—one of only 16 the entire year with Buddy Guy headlining.

I interrupted. “Wait, you’re going to Chicago for just one night?” Yep. “By yourself?” Yep. “Just to see Buddy Guy?” Yep. “Do you want company?” Without hesitation, he answered, “Sure!”

While we sipped our beer, he confirmed there were still SRO tickets for that same Thursday night show and he snapped one up for me. He forwarded his airline information, and I booked a seat on the same Southwest flight into Midway. Over lunch, we reminisced about our shared love of the Blues and Buddy Guy, the legend who inspired guitar luminaries like Jimi Hendrix and Stevie Ray Vaughan. No less than Eric Clapton said Buddy Guy had changed the perception of what a guitarist could do.

Later, when I told my wife about this spur-of-the-moment plan to catch a live Blues show, she was excited for me and asked if I would get to see our son while there. I texted him and asked if he could join me for some sight-seeing during my trip and he replied, “Definitely!” The next step was researching the top things to do in Chicago that my son and I might both enjoy. That wasn’t hard to do. After a few text messages and one phone call, we had a pretty full agenda of cultural highlights, crowned by several of Frank Lloyd Wright’s architectural masterpieces.

Two weeks later, I parked at the Jenkintown SEPTA regional rail station and boarded the 10:08 AM commuter train that would carry me to Terminal E at Philadelphia’s International Airport. A few minutes earlier, my friend had boarded the same train at the station nearer his house. I walked down the aisle in the second car from the front and found him. He greeted me and moved his bag off the seat so I could join him. Our talk quickly turned to another trip we hoped to take together later that year to Big Bend National Park in Texas, a place dear to him. We’d previously drafted a Texas itinerary while planning our Chicago trip, and by the time we reached the PHL terminal, we had booked flights, hotels, and a rental car for a memorable Big Bend trip, which might itself become a future series of blog posts.

Until quite recently, Southwest Airlines didn’t offer seat assignments, just boarding order. So, on our flight to Chicago that morning, we didn’t have seats together. As the plane roared to life for takeoff, I stuffed my AirPods into my ears and prepared for the show later that night, listening to the Buddy Guy CD titled “Slippin’ In” that I’d downloaded onto my iPhone. (Note the black-and-white polka-dot guitar Buddy’s carrying on the cover; it will appear again in later posts.)

Our flight lasted just an hour-and-a half and was mercifully uneventful; the highlight was when the flight attendants offered drinks and passed out yummy pretzel snacks: Stellar-brand mini braids, seasoned with Maui onion and monk fruit. (I enjoyed the same treat four days later on my return flight home.)

We gained an hour crossing into the Central Time Zone, and landed at Midway around 3:30 PM local time. Then we followed the airport signs to reach the Chicago Transit Authority platform for the Orange Line train that would take us to our hotel. We stepped on board and 20 minutes later, the skyline beyond Chicago’s South Loop opened up before us.

In the far distance, off to the left, was the soaring, black-sheathed Willis Tower, topped with narrow white antennas used for radio and television transmissions. Opened in 1973 and originally called the Sears Tower—the name still used by most Chicagoans—the skyscraper served as headquarters for Sears, Roebuck & Company, reigning as the world’s tallest building for nearly 25 years.

At the Roosevelt CTA stop, we gathered our luggage, rode down the escalator, and turned onto Wabash Avenue. Two blocks north, a modern high-rise with mirrored glass jutted up from the corner at 11th Street. I joked that might be our Hilton Garden Inn; it turned out I was right.

We checked in and were whisked upward in the elevator to our room on the 25th floor. Dropping our bags, we opened the curtain to reveal the spectacular panorama of Chicago up Wabash Avenue—today’s Featured Photo—with the Sears Tower again in the far distance to the left. But there was no time to waste: we wanted to be first in line at Buddy Guy’s Legends when the doors opened at 5:00.

(To be continued…)