Last night I drove to the end of Route 66, where the route hits Michigan Ave at Millennium Park. So this morning I got up and hopped on the ‘L’ downtown towards the Loop. The marked signs for the “Start” of 66 are a block off the subway. This is truly it. I’ve completed this journey, so far 5,000 miles in my car to get here. I have seen a lot on this trip, I did something every day that I’ve been on the road. From National Parks, to museums, to dirt roads, and the most random roadside attractions.
I still don’t know what I was really looking for while I was out here. I don’t know if I actually found myself or anything in general. So I guess I’ll be going back to work after all when I get home next week. Unless I go back through everything and maybe find a sign.








I booked one of those sightseeing hop-on and off buses, it picked up from the starting line of Route 66 and would drop me off at Navy Pier. Side Note, those hop-on and hop-off buses are great when seeing a new city. I did one in Amsterdam and did the Chicago one before with my parents. Sure, the subway is cheaper, but for travelers, this is easier than figuring out the subway system.










I hopped off at Navi Pier and found the Route 66 sign. It’s not like in Santa Monica, where they really claim the pier as the end. It was probably just a nice nod by Chicago to have the route be Pier to Pier. [My understanding is that Navy Pier is a more recent modern addition to Chicago, rebuilt and modernized in the 90s]. I took a walk to the end of the Pier, where there is a cool lighthouse you can see from the end, which sits at the opening of Lake Michigan. It was a really nice September afternoon, with a cool breeze coming off the water.














After grabbing a dog at the Billy Goat Tavern, I went to the bus stop to hop on the next tour bus and continue my ride around the city. We make our way along the shopping and architecture of Chicago. On top of the open-air double-decker bus, we have unobstructed views of the Chicago Cityscape.
When the bus returns to stop number one, I decide to get off since we’re at the Chicago River and right by Smith & Wallensky. This is where I went to celebrate my month-long adventure in Chicago back in 2018. Then I had a great steak dinner, some wine, and the most delicious piece of coconut cake. A dessert I’ve been thinking of for 8 years.

That dinner started off rocky. When I was seated, the hostess removed the wine menu from the table and walked away before I could say anything. When my waiter comes by asking if I want anything to drink, I say actually I’d like to see the wine menu. He immediately apologized and got me a wine menu to take a look at. I get, I may strike people as some one that stumblizes into a fancy steakhouse off the street, not realizing the cost. But I sought this place out, looking to treat myself to a nice dinner. After that, it was a good meal.
In my head, I made up this backstory for the waiter in my head. He seemed like a lifetime south sider, sox fan, family at home. Working a waiting gig at a fancy restaurant because tips were good, but he wanted to be doing something else. Anyways, I leave that fanfic for another day.
Tonight, the dinner was good, my waiter was a nice kid, despite him having other servers check in on me when it was still early and not very busy. The steak was good, it was tender and got a gorgonzola crust. I didn’t need it, but I got a side of Mac and Cheese. After finishing my meal, my waiter swung by asking if I wanted the dessert menu.

I say, Actually, I had a question and told him about the cake from 8 years ago. I ask whether you still have a coconut cake? He smiles and nods. I go OK, let’s do that. I had built up this cake for a while over the years. I would tell people about this cake in Chicago. When it arrives, this square slice of cake is covered in frosting and shaved coconut. It was a lot bigger than it was last time; the toasted coconut that was rolled and pushed through the cake was now a toasted coconut disk set atop the whipped cream with a coconut sauce drizzle. The presentation was different, but the important part was that the cake was still as good as I remembered. In short, no, the memory will always be better than the reality. The cake was good, it’s just that I had snowballed the memory of this cake for years.


After dinner, I walked around, took some photos of the famous Chicago Theater, walked back to Millennium Park, and had to take at least one photo of “The Bean” while I’m here, or would I even be a tourist? By the time I made it to my Airbnb, I was dragging. I just wanted to sit down and relax. The last 23 days finally caught up with me. Tomorrow I’m taking a break. Just going to hang out at the apartment, then go find a place to watch the Seahawks game. Friday, I see the Cubs, and on Saturday, I head west for my return home.



















