As the beginning of Route 66, Chicago has a lot to offer, some related to Route 66, some are not, but still fun and worth exploring. Many tour books suggest visiting a few more modern places. We did as suggested.
In Millennium Park, the Cloud Gate sculpture is nicknamed "The Bean" because of its intriguing shape. Made up of 168 stainless steel plates welded together, its highly polished exterior has no visible seams. The reflections are amazing, whether they are the city skylines or one's own figures.
This next photo is me seeing my own reflection.
There are currently three signs indicating the beginning location (for westbound, E. Adams St.) and ending location (for eastbound, E. Jackson Dr.).
Adams and Jackson are two one-way streets that are parallel to each other. On each street, we can see other Route 66 signs facing against the direction the road would be going (thus, travelers will see them). In the old days, when there was only one street, travelers would go from the beginning sign (close to the Art Institute) to continue out of town.
On March 25, 2026, the new begin sign will be installed on Navy Pier to match that in Santa Monica pier. As of today, the exact location is unknown.
Here is one place in front of the water.
It is said that this amazing place houses artwork by Vincent Van Gogh, Claude Monet, Pablo Picasso, Andy Warhol, and other famous artists.
We didn’t get inside the institute but just walked around the building. The four sides of the same building show very different views. There are two different names for the place: “Art Institute of Chicago” and “Art Institvte of Chicago.”
See for yourself in the photos below.
And why is Chicago reversed in this photo?
Lou Mitchell’s has been serving since 1923. It provides breakfast and lunch and closes at 2 PM. It is crowded, with both locals and travelers who would park their suitcases and luggage against a wall.
We had our breakfast there. The Norwegian Smoked Salmon & Onion Omelette was a huge portion that came with a piece of toast. We shared the meal. I also got my coffee of the day at breakfast, much later than my regular time, but well worth the wait.
Not part of the original Route 66, this building is a new feature of the “Windy City” of Chicago. The Skydeck at the top of Willis Tower is considered one of the best places to experience the city. At 1,353 feet (412 meters) up on the 103rd floor, the observation ledge’s glass boxes extend 4.3 feet (1.3 meters) from the Skydeck, providing never-before-seen views of the city.
We didn’t go up to experience the city. We just took some photos from the street level and in the lobby through the glass.
Centennial Route 66 Tour: Introduction
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