Rainy Chicago reflected in Sir Anish Kapoor’s Cloud Gate sculpture in Millennium Park
Chicago 36 Hours
We spent a rainy 36 hours in Chicago, “off season”, if a major metropolitan city can have an “season”! But most folks would prefer to be in the city during the mild spring or crisp fall season, or when they have time off in the summer, but we visited in the rainy late fall, which fewer people think of prime touring time. Despite the blustery weather, we were able to enjoy a lot of what the city has to offer.
During this trip, we decided to focus on staying at historic or boutique properties, although we also discovered that very few of them are independent anymore, and are usually part of a portfolio of boutique properties with one of the major chains. For this trip, we stayed at the Kimpton Monaco in the loop area. We found most attractions we wanted to visit, including the Art Institute of Chicago, and Millennium Park and river front to be within easy walking distance of less than a mile or so.
Lincoln Park Zoo
One attraction not near our hotel, was the Lincoln Park area and Lincoln Park Zoo, which we visited using our rental car. after our early flight into Chicago. We paid a high price to park in the Lincoln Park area, but the zoo itself is a free urban zoo.
Sky Deck
Later, after checking into our hotel, we visited the Sky Deck, the tourist attraction built in the former Willis Tower, at one time the highest building in the country. We often check out local “height attraction” early in our visit to give ourselves an orientation of the area. An early sunset meant we got to enjoy the glittery lights of the nighttime city and we didn’t encounter any lines or crowds.
We enjoyed a very well designed queuing attraction at Sky Deck, including a comprehensive history of the architecture in the city and interactive exhibits that allowed visitors to experience what makes Chicago unique. We arrived at the main attraction, a clear floor viewing booth, where you can experience the panorama of city. We caught glimpses of the city between floating clouds!
Art Institute of Chicago
One of the worlds best art museums, we used their well designed app to explore the highlights of this huge museum. One of the things we liked best about this museum, is that they have an excellent collection of American art and the museum reflects the place well, the city is even reflected through the panoramic windows in the newer wing. This is a museum that after you’ve visited, you don’t stumble back out onto the sidewalk forgetting where you are!
A 2020 portrait of Chicago resident, former president, Barack Obama by Jordan Casteel overlooks the area where his future library will be built.
Millennium Park
Our soggy first day in Chicago gave way to a wind whipped sideways rain, so our afternoon of exploring Chicago’s outside attractions, including the Navy Pier, and Magnificent Mile shopping district, was curtailed to just a brisk walk through Millennium Park.
This park built to welcome the new Millennium in 1998 as a park for arts and culture and includes huge performance spaces and public sculptures. The most famous is referred to as the “bean”, a beautiful reflective piece by Anish Kapoor called Cloud Gate, which we had mostly to ourselves on a rainy day!
Second City and Deep Dish
To round out our Chicago experience before moving west, we got tickets for Second City, the north Chicago comedy club that is famous for launching the careers of many A listers. We also dined on Chicago’s specialty- deep dish pizza!
