Route 66 has two endpoints: one is in downtown Chicago, which many people think of as ‘the start’ of the route (because of the order in the “get your kicks on Route 66”, song), while the other is (currently) at the Santa Monica Pier, just west of Downtown Los Angeles, which is where I started my trip. In Chicago route 66 is a little complicated as it exists on two one way streets, Adams, which travels west, and Jackson, which travels east. SINCE most people take 66 going west, that’s where you’ll find most of the signs…

Because Chicago is home and I’ve pretty much walked or driven most of these roads at one time or another without realizing they ARE 66, I have to admit that once I did, I opted to fudge it a bit once I passed Dell Rheas’s Chicken basket in Willowbrook IL (a town I’ve only ever passed by while driving on I-55) and felt that I had for all intents and purposes I had finished the route on the 24th of October. (I admit this is largely because I knew the neighborhoods I would be passing through… knew most of them to HIGHLY unsafe ones with nasty traffic. When I go downtown I stick to safe routes and park my car in safe areas.)

So for instance, the above are some photos of me in 2001 having dinner with friends at what was then arguably the best Greek Restaurant in Chicago’s GreekTown (on Halstead between Adams and Jackson … i.e., 66) the now closed Roditites Greek Restaurant, which used to be one of my favorite go to’s (it was open for 45 years). (All of the old Greektown classic restaurants seem to be closing, I think the children weren’t interested in taking over the businesses)but on the 31st of October I had business I had to deal with downtown, and as such took the opportunity to finish my 66 trek (only this time on foot, cause driving into the city is NUTS). I was staying at my friend’s home in Northbrook, and took the Metra Train from North Glenview station to Union Station, which is also located between Adams and Jackson (again, both are Route 66, it just depends on which direction you’re going) with exits to either street. Ironically, I have only ever been in this station once before. The Metra train line adjacent to my parents home went to a different station, the Ogilvie Center, a few blocks north. Unlike that station, which only services local lines, this station is where you go in Chicago if you’re taking an Amtrak line. As such, the only other time I was ever here was when I took the California Zephyr from Chicago to San Francisco back when I was in my late 20’s.The odds are you’ve seen this station before, even if you’ve never been to Chicago, as it’s been used more than few times in movies. The list includes Public Enemies (with Jonny Depp), My Best Friend’s Wedding (with Julia Roberts, Cameron Diaz and Rupert Everett), Man of Steel (one of the Superman movies), Derailed, and most prominently in the movie The Untouchables, about Al Capone (Robert De Niro) and Eliot Ness (Kevin Costner) … with a scene steeling Oscar worthy supporting performance from Sean Connery… which had a LOT of Chicago locations in it.

From the station I went straight to my 11am appointment, and then double backed to have lunch at Lou Mitchell’s Restaurant & Bakery (click link for my blog post about it), which is located a half block west of Union Station, and is probably the only historic Route 66 eatery to be in the Michelin guide. After lunch I walked back east, along Adams (Route 66 west bound) past Union station and to the Chicago River which forms the station’s eastern boundary.

If you ever come to Chicago I strongly suggest taking one of our Water Taxi’s from Union Station (i.e, Route 66) to Navy Pier (the Orange line on the map above) which travels to where the Chicago River meets Lake Michigan… that said I’m about to go a bit off topic, but really… you have GOT to try the water Taxis

While at Navy pier, before switching to the next Taxi, you might want to go up on the Ferris Wheel (which is sometimes referred to as the Chicago Wheel, as it actually served as an attraction back in 1893 at the World’s Columbian Exposition, i.e., the White City, which was held along the lake on Chicago South’s side) which offers some great views of the city

but then make sure to take the Water Taxi that travels from the pier via Lake Michigan to Shedd Aquarium and the Field Museum, even if you don’t want to go to the Museums.

The skyscraper on the left is the Big Willy (see below), the one in the middle is the Standard Oil building — no self-respecting Chicagoan refers to it as the Aon center and if you asked them where the Aon center was I doubt they’d know, and one to the right is the John Hancock (where I used to work back when I was in my 20’s)….. again, NO ONE calls it 875 North Michigan Avenue. Apparently the John Hancock building, the corporate headquarters for the John Hancock Mutual Life Insurance Co, at around 2013 ceased to be their headquarters, and just a few months ago the name got changed to its address. The pics above were from when I did this back in 2013 when my friend, who I knew from when I was teaching in S. Korea, came to visit during a summer break.

But I digress…  returning to Route 66….

From there I continued my trek down Adams (the west bound 66). The above picture is looking west down the street, across the bridge I had just passed over… and, the ‘small’ white building just above the black van is Union station.

Again, this photo is looking west. The sky scraper in the distance is the same one shown in the picture from the Water Taxi. Which I referred to as “The big Willy.” It was originally called the Sears Tower (my best friend from high-school has worked there for almost 15 years), and when first built in 1973 (I remember it going up) it was the tallest building in the world. But Sears then sold it to Willis Insurance in 2009, who renamed it as The Willis Tower. Many Chicagoans to this day absolutely refuse to use that name, but I, personally, LOVE IT… because it allows me to call it “the big Willy” (Willy being a British slang word for penis) and just how great is that?! The GORGEOUS historic building in the foreground of the picture is the SIDE entrance (if you can believe it) of the Rookery Building, which designed by deeply important architectural firm of Burnham and Root in 1888. If you have ever read the best-selling novel The Devil in the White City: Murder, Magic, and Madness at the Fair That Changed America, about the Chicago world’s fair, you know who they are. I didn’t take any pictures inside, but the lobby was design by Frank Loyd Wright. If you’re an architecture enthusiast you will LOVE Chicago.

Another thing Chicago is famous for, one of which is visible on Route 66, is our collection of public art. The above is Alexander Calder‘s Flamingo (sculpture). I remember when it was first unveiled in 1974, none of us could make heads or tails of what it was… but it’s pretty.

After this I pit stopped off at the historic Berghoff Restaurant (click the link for a fully review of the place) for a mug of their root beer (they brew it themselves). For some reason this iconic German restaurant which is a landmark of downtown Chicago, its been there since 1898… is NOT in the Michelin guide… shrug?… I remember the first time my mom took me here, I couldn’t have been more than seven or eight years old. If you look at the image above, and look down the street between the tall building you’ll see the roof of the Art Institute of Chicago, which is not only one of the FINEST art museums in the world, it’s also my Alma Mater. If you love German food, EAT HERE, this place has been rocking my socks off my whole life… if you don’t… at least try the root beer and look around, the interior is just amazing to look at and reeks of Chicago history (photos and murals of Chicago Exposition line the walls)

AND THIS is also a route 66 establishment — and I never realized it was that until this trip. Did I mention I have been eaten here my whole life.

If you look carefully at the building, you’ll see how the sign above… which I’ve never seen before, and keep in mind the roman looking building is Art Institute of Chicago, were I went to school for four years….. and this one below are on either end of the same city block…