Chicago, Illinois

3 to 7 September 2021

Downtown Chicago from Adler Planetarium Skyline Walkway

Chicago, sitting on the shores of Lake Michigan, is the third largest city in the United States.  We originally planned to visit in March of 2020, the start of the Covid-19 pandemic.  Labor Day weekend gave us an opportunity to reschedule the trip.  We arrived at O’Hare Airport Friday evening and enjoyed three full days before our return flight on Tuesday afternoon.  The downtown is pedestrian friendly, and despite what you might hear on the news, feels very safe.

We stayed in the Weston Hotel River North which was central to the most popular tourist attractions.  Perched along the north shore of the Chicago River within a few blocks of Michigan Avenue, we had easy access to the River Walk, Grant Park, Cloud Gate, Navy Pier, Lakefront Trail, Lincoln Park and the Magnificent Mile.

Skyline from the North Shore (top), St. Regis Tower (middle-left), Cloud Gate (middle-upper), Architectural Boat Tours on the Chicago River (middle-lower), Marina City (middle-right), Start of Rt. 66 (bottom-left) and Chicago River at Night (bottom-right).

Chicago is known for many things, Air Jordan, deep-dish pizza, Jazz, Prohibition-era mobsters such as Al Capone and Baby Face Nelson, da Bears, Lollapalooza, and skyscrapers.  Architectural tours given from boats on the Chicago River are very popular.  In a city full of engineering marvels, the Sears Tower is perhaps the most recognizable.

When it was completed in 1974 for the Sears Roebuck Company, the Sears Tower was the world’s tallest building.  It was renamed the Willis Tower in 2009 for Willis-Tower-Watson, one of the world’s largest insurance brokers.  I wonder how Watson felt about that?!  Today it is the third tallest in the United States behind One World Trade Center (2013) and Nordstrom Tower (2021), both in New York City.  Trump International Hotel and Tower (2009) almost surpassed it as the tallest in Chicago.  In 2001, Donald Trump announced it would be the tallest in the world but after the September 11th attack it was scaled back – renting space in the tallest building was no longer desirable.  Posting this on the 20th anniversary of 9/11 and less than a year from surviving the Trump presidency, the story of how the Willis Tower remained the tallest in Chicago resonated with us.

Sears/Willis Tower from Street Level (left) and from River City (right)

On Sunday we got tickets for the Pirates/Cubs baseball game.  Wrigley Field is one of America’s most iconic stadiums.  From the ivy covered outfield wall, to rooftop seating on adjacent buildings, to the surrounding neighborhood of Wrigleyville, Wrigley Field is a special place.  Built in 1914, it has been home to the Chicago Cubs since 1916.  It was also home to the Chicago Bears from 1921 to 1970.  It got its name from William Wrigley Jr., founder of Wrigley Gum, who built his company with aggressive marketing and used his proceeds to buy the Cubs.  Despite their dedicated fans, the Cubbies had not enjoyed much success until they won the 2016 World Series, breaking a 108 year long drought since their last championship.  The field has received National Historic Landmark status, cementing it as one of the great sports venues.

Wrigley Field

If you enjoy the big city, it is hard to beet a weekend in New York City, but Chicago is a strong contender and certainly worth it.

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