A Weekend In Chicago
What a great weekend! At least as far as my trip to Chicago was concerned. It was really a top notch trip, as Judge Smails would call it.
I don’t know if this will be as detailed as some of my old trip summaries were, but here’s a general accounting of my 48-ish hours away.
Travel
Driving up to Chicago is a breeze. Even Friday morning, when I was passing through multiple areas where tornadoes had been Thursday evening. I saw some trees down, a few road signs destroyed, but that was it. I could have made it all the way to our weekend rental without charging, but decided to stop in Munster, IN so I had enough juice to get through the weekend. I also topped the battery off while we were killing some time before our rental was available. And I stopped to charge for about 15 minutes on the way home mostly so I could pee. I’m currently using some referral credits to pay for charging, so it was all free, but I’m guessing this all would have cost about $45–50. Compared to two tanks of gas in this economy??? A bargain.
I picked up my brothers-in-music Sir Dave and E$ at O’Hare and after that time-wasting charge, we got to our rental right at check-in time at 1:00.
The drive back was a little less easy, only because I was routed through the Chicago Skyway, which involves going through three, old school toll booths, which turn a 20 mile stretch into a 45 minute slog as you wait through three lines. Friday on the way up I was routed west, where all the tolls are drive through gates that you don’t slow down for. Time to modernize, Skyway folks.
Rental
We were staying at 900 S. Clark Street, on the 16th floor of a building. We had very nice views to the west and south. Our rental was rather spare in accommodations but gave us a nice place to post up and sleep.


Food
We had two terrific meals, both for lunch.
Right after we arrived we walked a couple blocks to the Eleven City Diner which was wonderful. It is an old school, big city diner. Sir Dave and I both ordered massive, corned beef and pastrami sandwiches. Ten years ago I would have put it away with no troubles. At nearly 55 I was still able to finish it, but I’m not going to say it sat well in my stomach the rest of the day. The order of fries and chocolate shake probably didn’t help.
That evening we had bar food while watching the US World Cup game.
Saturday for lunch we went to Half Sour where I had the best breakfast burrito I’ve ever had. I can’t quite describe what set it apart – perhaps it was the proper steak inside – but they did something different and tasty with the tortilla as well. Sadly it is not listed on their online menu so I don’t know if their secret is listed there.
That evening we had access to a VIP buffet at the concert, which was a little disappointing but gave us enough energy to get through the night.
Activities
After lunch Friday we strolled over to Grant Park and meandered a bit. Our plan for the afternoon was to take a boat architecture tour on the Chicago River. We decided it would do us all well to extend our walk up to the pickup area so we weren’t completely miserable on the boat. It was bordering on toasty by this point, so we rewarded ourselves with a round of beers before the tour began.
If you’ve never done one of these boat rides, drop everything, get to Chicago as quickly as you can, and take the first tour you can book. Preferably with Charlie as your guide. This man was completely spectacular. He spit knowledge about the city, its buildings, and their shared history nearly non-stop. He threw shade at other cities, notably New York (which has never had a Pope) and St. Louis (which is where all the trash the Chicago River removes from Chi-town belongs). He celebrated his hometown. He was absolutely amazing. We all agreed later that he might have been too good. He shared so much information that we had a hard time recalling it later. Don’t let that scare you off. The highest recommendation.

Our plan for Friday evening was to watch the US World Cup game, hopefully at a classy sports bar. E$ had also found a cool looking Irish place called Fadó on West Grand Ave. We arrived well over an hour before the game, but there were no open tables anywhere in the building. Shame because the place had a lot of character and was filled with soccer aficionados.
We had passed a couple other places on our way to Fadó so circled back to Mother Hubbard’s, which had a totally different kind of character. A traditional Chicago dive bar with a ton of TVs. We found a table and settled in for several hours. The game was, obviously, fantastic. The crowd here was a little different than it was at Fadó, but still fun to watch a big US win in a crowded bar.
We celebrated the win and the balmy evening by walking 30 minutes back to our place. Love big, walkable cities!
Saturday was concert day, so emotions were high early. We began the day by grabbing coffee and breakfast sandwiches at the Starbucks in the Target a block away. What a country!
After getting our caffeine fix we headed back to Grant Park with the hopes of spending the morning in a museum. The Shedd aquarium was rather pricey, and I had already been there. The Field Museum had a more reasonable admission and ended up being a fine way to pass a couple hours. Proper museums that you can get lost in are one of the great joys in life. I took a lot of pictures of dinosaurs for my nephews back in Indy.

Back to our rental for some downtime and preparations for the evening.
Our pre-concert plans included grabbing a drink with another old KC friend who now lives in Chicagoland. We met him at Weeds Tavern, the self-proclaimed best dive bar in Chicago. It was a nice little spot to have a few drinks and catch up. There was a decent sized group of guys there who had been out playing golf, most of whom were wearing IU gear. There was a dude playing pool wearing a KU shirt. I felt like I was in the right place!
THS Live
Finally it was time for the show! We had about a 20 minute walk from Weeds to the venue. Our pre-game drinks meant we were showing up around 6:00. The opening bands were scheduled to begin playing around 4:00. No big deal. But when we arrived the final opener was playing. We later learned that because storms were forecast for later in the evening, the entire lineup had been moved forward an hour. So we got to hear four Built To Spill songs and then The Hold Steady took the stage just after 7:00. At least we got there in time!
The show was predictably outstanding. I had not seen THS in person before, but I’ve seen plenty of videos of their performance so know they were terrific live. They lived up to that reputation. They opened with “Stuck Between Stations,” “Chips Ahoy!” was second. Two of my five favorite songs to start! As this show was for the 20th anniversary of their Boys And Girls In America album, they played every song from it. We got “Stevie Nix,” “Your Little Hoodrat Friend,” and “Sequestered In Memphis,” likely my next three fav THS songs. Every bit of it was great. For a bunch of guys in their mid-to-late 50s, they can still bring it. Probably helps that they only play 20 or so dates a year these days, so they can recharge in the months between shows.
The show was at The Salt Shed, a new-ish venue built around an old Morton Salt facility. It is a very cool site, with lots of bougie accoutrements rock ’n’ roll lovers in their 50s can appreciate. When THS first came out we were still in the upper balcony area. We watched a song from up there then worked our way into the main floor section. The sound was much better down low. I felt like asking them to play “Stations” again so I could get the full effect. The night was gorgeous, the music was glorious, and the company was great. A fine night all around.



We knew ahead of time that the Salt Shed has a strict 10 PM stop time for shows, so we were counting on being done early. But with the weather adjustment, we were done before 9:00. Which felt a little weird.
We humped it back to Weeds, which was now packed. We watched a bit of the NBA Finals game but felt old and out of place, or at least I did, so Ubered back home and watched the Knicks complete their comeback there. That result was the only bummer of the weekend.
Well, it was also a bummer that it was raining Sunday morning so we couldn’t wander our area and find a quick breakfast before I took the guys back to O’Hare for their flight back to KC.
It had been nine or ten years since my last trip to Chicago, and that one was in the winter so my time outside was limited. As mentioned already, there is a real joy to large cities that have lots to see, eat, and do, and can be navigated on foot. My calves are still sore from all the walking. I’m not sure I could ever live in a place like Chicago, as I like my space and I think the traffic would drive me insane. It is a fantastic city to spend a few days in, though, especially when the weather is nearly perfect.