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We flew direct from London, Ontario to O'hare Airport on United Airlines. The London airport is convenient to our home and, as it's a small airport, is an easy airport to park and navigate. Unlike Toronto, you go through US customs and immigration when you land in Chicago. Over the years there's always been a few regular direct fights into the US (we used to fly direct to Pittsburgh, then to Detroit, and now to Chicago).
From the airport it's a quick ride on the metro system to downtown. You could take a cab but the metro was much faster. We stayed north of the river near North Michigan Avenue and spent a couple of sunny days exploring the city. We ought to have stayed longer, there's a lot to see.
The most memorable part of our visit was a river cruise by the historical society (there are a lot of river cruises -- look for one where the guide is from the historical society). It's a city of bridges and tall buildings and there are lots of views of both from the water. The history of the river is interesting. It used to be an open sewer with consequent water borne epidemics as they take the water from the lake (and the river dumps into the lake). They "solved" that problem by digging a canal which reversed the river flow so it drained into the Mississippi River ... and sent their sewage down river to cites like St. Louis. These days the river is pretty clean and the city has embraced it. Old buildings ignored the river and present a blank wall. These days there's cafes and walk ways along the river with buildings fronting the water. I understand that any urban development along the river must, as a matter of law, include an urban walkway along the river front.
I explored the Chicago Art Institute -- a world class gallery you really ought to see. The Millenium Park along the water front, where the Chicago Art Institute is found, has some great art installations and odd buildings as well. The photo above is the Jay Pritzker Pavilion in the park. It's an outdoor concert venue.
I also visited the library and went up to the Willis Tower (formerly known as the Sears Tower). There's a couple of viewing platforms where you walk out onto a glass floor. A bit terrifying.
One evening we went for a walk along the lake shore. It was still warm enough for swimming.
Here's some photos from our visit.