Railway Rick - 01: My Kind of Town

Chicago was a blast.  But this first journey started 3 nights earlier at the Syracuse Amtrak station. That place is a ghost town on a Saturday night. I was confident I would have a seat to myself all the way to Chicago. But as the departure time got closer, the station began to fill with a large Amish group. Speaking maybe Dutch?  And then a wheelchaired passenger was parked about 20 feet from where I waited. Oh that was a smelly man. What was I in for on the train?  But all was well and I did indeed have a solo seat, as did everyone else that wanted one in our “Chicago” car. Anyone not getting off in Rochester, Erie, etc was put together in one car so we could not be bothered all night with passengers getting on or off. Nice. 

I was exhausted so I got some sleep between 11pm and 7am. Not totally restful as the sounds, and the motion, and the need to change position woke me every 20-30 minutes. But I went right back to sleep. Noise canceling headphones and an eye mask were a must. They also turn down the lights and stop making announcements between 11 and 7.  Very helpful.  Coffee at 7am from the cafe car and then stared at the boring countryside through Northern Indiana. And the final bonus of the trip, we arrived almost an hour early into Chicago. First trip completed. 

Took a long walk from the station to the hotel carrying my heavy duffel.  Yes Carol, I should have taken one with wheels.  Checked in early and got some rest before the Bears game. Closer to game time I expected the prices online to come down. But nope. This town is football crazy so the tickets were quickly disappearing online and the prices were going up. Oops. Oh well, I got an upper deck seat with a great view so I wasn’t disappointed. It was an incredible fan experience at Soldier Field. Great music; the fans knew when to sing along to the Bears videos and the fireworks show after every score. And the Bears decided to play well and they destroyed the Cowboys, much to the disappointment of many Dallas fans in attendance. A cap tip and shoutout to brother-in-law Dan, a huge football fan in his own right. 

After the game I hopped a bus up the Chicago Riverwalk area to the Aire rooftop bar atop the Centric Hotel, where I had a tabletop seat for a Sinatra tribute concert. The small 4 person band was great, especially the horn and bass. The singer was good and sounded a bit like Frankie, but he was over the top at times trying to imitate mannerisms, etc.  And he didn’t sing “New York, New York”.  Wtf?  But he redeemed himself slightly in his encore of “That’s Life”, and “My Way”.  Enjoyed a small dinner and some drinks during the concert. The weather that evening, and during the entire stay, was warm and wonderful. Great time and a nice leisurely walk to the hotel afterwards.  That was a full Sunday. I enjoyed my bed that night!

Monday morning I had a big breakfast at the diner next to the hotel and then had a short walk on Michigan Avenue. 

 

 

 

Hopped on the Big Red tour bus and rode around the city for 2 hours. I was expecting some audio commentary but there was none. Still a great way to see the city. There were about 10 stops along the way but I just stayed on for the entire loop. 

 

Enjoyed lunch and a Jamesons Stout at an Irish Pub when i returned. 

Later that afternoon I hopped back on the Red bus back up to river area. Rode the 90 minute Chicago Architecture Tour boat up and down the Chicago River. That tour came with a very good guide who explained a lot of history and architecture along the way. I especially liked the Carbide building that was constructed during prohibition. It was modeled it to look like a champagne bottle including some gold foil near the top, and also making the top look like a big middle finger. A big “F U” to prohibition! Another highlight was the old Chicago Post Office.  It was used as Gotham National Bank in Batman Begins and The Dark Knight. It has been remade into multi-use offices today and the rooftop is a 3.5 acre park with a track, basketball and pickleball courts. 

 

 

 

 

 

Then it was time for my Monday highlight, a jazz show and dinner at Andy’s Jazz Club. When I made my reservation online, it was stated that parties of 1 would be seated at the bar. They lined up 4 of us “party of 1” guys right next to each other. I dubbed it the Lonely Man Jazz Club; just my internal joke; I certainly wasn’t going to talk to strangers. Lol. As expected the jazz band was outstanding, about 15 musicians!  And for about half of the 90 minute set, they had a female vocalist, Tatum Langley. Great voice!  Ironically, she recently completed a tour with the band Postmodern Jukebox. The coincidence there is that my favorite singer Haley Reinhart also toured with them for a while about 8 years ago. Tatum was hawking an LP she just completed, so who am I not to help out a young singer?!  Good thing Michelle has a turntable so I can listen to it. And since I bought her album, Tatum autographed it and took a selfie with me. A good night. A good dinner as well. I didn’t get my deep dish pizza as I had hoped but I had a good Chicago steak and a great crab cake at Andy’s. I enjoyed my long walk back to the hotel this time.  

The last morning was laid back. I was going to make my way to the John Hancock building and visit the top observation floor that has views in all directions, hence the name “360 Chicago”. But it was cloudy and I was done with rushing around. Instead I took a 2 hour self-guided walking tour around downtown. Only problem with that was getting caught in a brief rain shower. Oh well. 

 

Back to the hotel to grab my bags and take a Lyft to Union Station. I sat there staring at the fancy staircase in the station’s Great Hall, and I couldn’t help but think of Kevin Costner on that staircase in The Untouchables, shooting the Capone gang with a gun in one hand and diving and catching a baby carriage with the other hand. 

The #7 Empire Builder train on Sunday afternoon had some kind of issue on the first night and arrived 4 hours late to Seattle today. Yesterday’s version is doing better and is still on time for arrival in the Emerald City tomorrow morning. I only hope mine has the same good fortune the next couple of days. I’m on board now and so far so good as we departed on time. 

Goodbye Windy City. Now I’ll chill on a long 45 hour train ride through to the west. Wisconsin, Minnesota, North Dakota tonight. Most of the day tomorrow will be spent in Montana. Hopefully in Seattle mid morning on Thursday. See you next time.