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Swayed by "The Windy City"

Writer's picture: G. RhodesG. Rhodes

Chicago's skyline easily ranks among the world's most magnificent with its picturesque lakefront setting.

I’ve had the good fortune to visit Chicago for business on many occasions and have always been impressed by the city’s vitality and cosmopolitan vibe. Several years ago, I enjoyed the opportunity to visit strictly as a tourist in order to catch up with some good friends from the United Kingdom who had decided to take an anniversary holiday in "The Windy City.” Situated on Lake Michigan in northeastern Illinois, Chicago is one of the largest in the US. Noted for its bold architecture, the city also lays claim to any number of wonderful museums and many fine restaurants catering to nearly every taste. Chicago’s “easy to get to” from most anywhere in the country or the world by flying directly into O’Hare International Airport. Located some 14 miles northwest of the downtown business district, O’Hare’s eight runways helped it support over 2,500 aircraft operations per day in 2019, making it then the world’s sixth-busiest airport serving more than 84 million passengers. As the first major airport planned after World War II, O’Hare’s innovative design pioneered concepts we take for granted now such as concourses, direct highway access to the terminals, jet bridges and underground refueling systems.


The AAA Four Diamond Hyatt Regency Chicago is the largest hotel in the city and boasts a prime location.

During many prior business trips, I found the Hyatt Regency Chicago Hotel to be a pleasant place to stay and conveniently located. It’s the largest hotel in the heart of downtown and just steps from the Chicago Riverwalk. Located on East Wacker Drive, this hotel has over 2,000 rooms and suites (divided between East and West Towers) as well as six restaurants and lounges. Ideally situated between the Chicago River, Lake Michigan, Millennium Park and upscale Michigan Avenue, the Hyatt was the perfect choice for this leisure trip. A recent $168 million renovation enhanced the entire property and included revamped guest rooms and meeting spaces as well as a new, massive, light-filled lobby. At check-in, I was pleased to learn I’d been upgraded to a King-bedded room on the Regency Club level, the top floor of the West Tower. My assigned room was spacious and comfortable featuring a signature Hyatt Grand Bed and a nice work area with multiple outlets. An added bonus was the nice view of the Chicago River leading towards Lake Michigan. The Regency Club was open daily from 5:30a to 11:00p, serving both hot and cold breakfast options along with evening canapés and a self-service honor bar. My friends had checked into the W Hotel in the Gold Coast section of Lakeshore Drive which was only a few minutes away from the Hyatt by cab. They were very impressed by both the room and its decor. We met at their Rooftop Bar on our first evening. It appeared to be “the” place to be in Chicago that night!


Good food and good service made Morton's an ideal place to spend a memorable evening with friends.

Dinner later that evening took place at Morton’s The Steakhouse, a top-end chain near the Hyatt which is noted for its aged, prime beef, seafood and other traditional steakhouse fare served in what can best be described as a clubby space. The menu reflects many of the classic dishes that made Chicago famous, including ribeye and center-cut filet mignon along with jumbo lump crab cakes and several varieties of fresh fish. It’s fine dining for those with a hearty appetite and we were certainly not disappointed. (Except for the broccoli which was apparently improperly stored making it tough and so chewy, we referred to it as “ROCKoli.”) In typical Morton’s fashion though, it was quickly and cheerfully replaced with a different vegetable and we continued to enjoy a great evening reminiscing about many past adventures.


Chicago is known the world over as the birthplace of the skyscraper. We sailed past many on our river boat tour.

The next morning we hopped aboard a Chicago River Boat Architectural Tour. Forming a length of 156 miles when combined, the Chicago River is a system of rivers and canals that help to characterize the Chicago skyline today. In 1887, the river’s flow was actually reversed through a monumental feat of civil engineering with the construction of canals to reverse the flow towards the Mississippi River thus diverting sewage away from the fresh water supply of Lake Michigan. We learned how the Great Chicago Fire of 1871 destroyed roughly 3 square miles of the city’s wooden structures and left over 100,000 persons homeless. From this enormous calamity, the city was rebuilt and the skyscraper of structural steel and plate glass was born. It was a beautiful day and our 90-minute tour aboard one of the Chicago Line’s cruise boats was fun and informative. As we sailed past any number of architectural landmarks, our docent shared stories behind many of them along the river, including the Tribune Tower, the Wrigley Building, the Trump Tower and Marina City to name a few.


All things Boeing can be found at their Gift Shop in Chicago's West Loop area. I found it hard to leave.

Ever the AvGeek, I took myself to the Boeing store after the cruise. Located in their Corporate Office Complex at 100 North Riverside Plaza, the store carries all sorts of official Boeing merchandise. This includes a wide variety of logo apparel items, including activewear and workout gear. They also carry numerous collectibles, drink ware, plane models, STEM toys, electronics and so much more. I felt like a kid in a candy store and could have happily spent all day there. If you can’t make it to Chicago to shop in person, you may do so online.


The Willis Tower is a noted Chicago landmark which took 2,000 construction workers three years to complete.

We next visited the Skydeck at the Willis Tower. When completed in 1974, this 108-story building surpassed the World Trade Center in New York City to become the tallest building in the world, a title it held for nearly 25 years! It was also the tallest building in the Western Hemisphere for 41 years, until the new One World Trade Center was completed in 2013. Interestingly, the building’s largest tenant is United Airlines, which moved its corporate headquarters here in 2012, now occupying some 20 floors. The Skydeck on the 103rd floor is the highest observation deck in the US at an elevation of 1,353 feet. This is one of Chicago’s most famous tourist attractions drawing about 1.7 million persons a year. Elevators reach the top in about 60 seconds and on a clear day, you can see far over the plains of Illinois and across Lake Michigan to Indiana, Michigan and Wisconsin.


The minimal five-sided glass balconies provide an experience that feels like you're suspended in mid air.

But the real star of the Skydeck is The Ledge, a series of clear enclosures that extend out from the building offering views straight down over the city itself. Inspiration for The Ledge came from the hundreds of forehead prints left behind on the Skydeck windows each week as seen most notably in a memorable scene from the movie Ferris Bueller’s Day Off. They’re individually made up of three layers of half-inch thick glass laminated into one seamless unit and are built to withstand four tons of pressure and 10,000 pounds! Each Ledge box is four feet deep, ten feet high and ten feet wide. They have “heat tracing” to melt snow and also retract into the building for easy cleaning and maintenance. Having said all that, the experience is still unnerving and we swore we could hear cracking noises while standing over 100 stories above the ground. (In June of 2019, the protective layer of one of the Skydeck Ledge’s glass bottoms actually did crack under visitors’ feet. Building engineers said no one was ever in danger.)


One of the most popular restaurants in town, Joe's Stone Crab always delivers fine food and top-notch service.

For our final night’s dinner together we chose Joe’s Seafood, Prime Steak & Stone Crab, one of my favorite Chicago restaurants (there are others in Las Vegas and Washington, DC). At 60 East Grand Avenue, this one is one of the most beloved and widely

recognized restaurants in the city, famous for its Florida Stone Crab, generous steaks, signature sides and Key Lime Pie. It’s always busy and sometimes difficult to secure a reservation so plan ahead and you won’t be disappointed. We sure weren’t and enjoyed the nice surroundings, delicious food and excellent service. The evening ended on a funny note. As my friend’s wife was returning to our table, she was approached by another guest inquiring, “Excuse me, but is that man at your table Ricky Gervais?” I'm not sure how she responded but would guess my friend's slight resemblance to the English comedian and his British accent are what prompted the question. Either way, I'd say it's nice to be noticed!


I said farewell to my friends at the close of the evening and headed home the next day, enjoying the opportunity to act like a tourist in Chicago for a change.


Until next time…stay safe.





3 Comments


Joseph Donohue
Joseph Donohue
Mar 01, 2021

Although your visit was a summer one, I was thinking about you last week since it was Midwinter. Hope all is well!

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Peter Rees
Peter Rees
Feb 28, 2021

Great memories George - well presented - almost feels like I was there !

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bjrhodes001
Feb 28, 2021

With this trip you are bringing back some of my memories. I visited Chicago with my AORN buddies several years ago. We splurged and stayed in the same hotel but did not enjoy the same restaurants as you did. Our deal was the Chicago Deep Dish Pizza!! With your in depth information it make me want to go back and do it your way! Thanks again, as always. ❤️

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