The next leg of my journey was from NYC Penn Station to Chicago Union Station. The train was the Lakeshore Limited. It was incredibly spacious, even in coach. There is extra leg room, extendable tray tables, and curtains for the windows. The ride ended up being approximately 22 hours, two hours later than anticipated due to several freight trains passing us along the way.
This was my first overnight train, ever. I was fortunate to be in a row alone. Because of this and how spacious the seats were, I was not worried about getting enough rest. After working for a bit I decided to get some shut eye. I found that it was more comfortable to just recline in my seat instead of utilizing both seats because of the way the arm rests were set up. I did not sleep through the night, but got in several long spurts. Everyone on the train was quiet once it got dark, so earplugs were not necessary; however, my eye mask came in handy because they did keep the car relatively lit all night for safety purposes.
In the morning I felt rested. I logged on and worked for several hours prior to arriving in Chicago. Once I stepped off the train, I had that post-treadmill feeling while I walked. I found a café nearby to take some meetings, but also to sit down for a while and lose that shaky feeling.
Once the workday was over, I made my way to the L (the Chicago train) and rode to my friend’s apartment. She moved to Chicago the week prior to my trip, so it was perfect timing! We put together a new couch and got some very delicious Thai food for dinner. I then took myself out around the city, again trying to maximize my time there. I had been to Chicago once before, (in the winter) so I did not feel the need to do a lot of the touristy things again, which really freed up my options.
I went to a fun, entertaining rooftop bar called Utopian Tailgate in Old Town Chicago. The city of Chicago is much larger and spread out than I previously remembered. Chicago has 200 neighborhoods that make up 77 community areas. The population of Chicago is approximately 2.7 million according to the 2020 census, making it the third largest city in the United States, behind New York and Los Angeles. Each neighborhood has a very different feel to it. Old Town was first settled by German immigrants and is now home to Second City comedy club and many other bars but is known for its Victorian-era architecture and boutiques.
The next day, I went to Tweet for brunch with friends where we got some great cocktails and even better eggs. It is located between Uptown and Edgewater, right next to the beach and it is a brunch spot by day and bar at night. Afterwards, we hit the beach…or lake? It was a warm and windy day. The water was too rough to swim in, but we enjoyed the sun and people watching all the same.
Several hours later, we regrouped with some deep dish and thin crust Chicago pizza from Lou Malnati’s and a picnic in the park. I couldn’t leave the city without having some deep dish, but honestly, I was slightly disappointed. It tasted…fine…but I only had one piece. The thin crust was much more flavorful and satisfying.
In the evening, we made our way to a local brewery. It was very low key and had a lot of variety in the beer selections. Our night ended with some Mexican food that hit the spot much more than the $1 slice of New York Pizza from a few nights ago. There is nothing like some cheap, delicious, late-night, enchiladas.
The next morning, I headed to the international McDonald’s in the West Loop, where my uber driver did not care that I was on a time crunch and took the scenic route to show me some essential Chicago history. I wanted to go to this McDonalds because it features items from McDonalds menus across the globe. However, that day they only had 3 items…a plant-based burger, potato wedges, and a pretzel and caramel Mcflurry. Naturally I got all three because I was committed at this point. They all tasted all right, but it is McDonalds so my expectations were low.
My plan was to walk to the train station afterwards, but because my first uber was so slow, I had to get another to get to the station on time. After hustling to my track, the train was delayed indefinitely. It did not end up leaving until 3 hours after its original departure time…
I knew going into this trip to expect delays. I am flexible but, the thing that bothered me, other than the folks who were impatient, was the lack of communication from Amtrak. I had to keep refreshing the app, which was always slow to update, to get an idea of when the train might be coming because the workers in the station had no information. Regardless, I successfully made it to Minneapolis for the next leg of my adventure!
USA Rail n Road Trips 