If I had to award anyplace in the US “friendliest city”, it would be Chicago. I’m not sure why a city that rivals New York in size would be seem so much friendlier. It may have something to do with being slightly less compact and having a less frenetic business culture. This has become one of my favorite places to visit. I have attended multiple conventions here. During each visit I have relished the abundance of museums and arts.

Chicago has a huge blues culture of its own that has developed a unique style from that of the Mississippi delta, the origin of the genre. One of my favorite activities has been bar hopping to explore the smorgasbord of local styles.  Artists turn over multiple times during the night.  So you can just pick a neighborhood and meander back and forth between the venues until  you find a groove that speaks to you.

If you are able to visit during the week-long “Taste of Chicago” festival, you’ll experience one of the nation’s largest outdoor culinary celebrations with a treasure trove of music on the city’s largest park along Lake Michigan.   Grant Park has a massive tiered fountain called Buckingham Fountain that is impressive to watch in the evenings when it is illuminated against the city-scape.

Buckingham Fountain
Buckingham Fountain

Just in the spirit of celebrating architecture, I recommend the John Hancock or Sears Tower. These are the two tallest buildings where you can best appreciate the scale of the city’s spread below you.

The Art Institute of Chicago is worthy of a full day’s dedicated visit. It has many famous masterpieces including one of my favorites, the pointillist painter Georges Seurat‘s massive Parisian landscape “Sunday in the Park at La Grande Jatte.”  Pointillism is a meticulous impressionist art style where the painters would cluster multiple dots of primary colors close together, which the eye fuses together into an image much like a TV set builds an entire image from individual electrons hitting red, green and blue pixels on a screen.

Sunday in the Park at La Grande Jatte

If you happen to be a Vincent van Gogh fan, you’ll find his self portrait and his painting of his bedroom that you’ve probably seen depicted elsewhere as well…

There is a small collection of Claude Monet‘s impressionist paintings including one of my favorites depicting haystacks at dusk.

The Field Museum of Natural History has a dinosaur and fossil collection that I think is on par with the Smithsonian’s collection in Washington DC. Stroll through a herd of small velociraptors, with your head at armpit level, thanking fate for your separation in time during proximity in space.

The exhibit feels very intimate, allowing you to see the most elaborate trilobites up close.

Take me home:

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