A Breath of Fresh Air: My Time in the Windy City

Greetings from Sykesville, MD, where I'm officially well over a month behind on blog posts. Maybe someday I'll catch up...

In Chicago, I stayed with my old college roommate Matt, his wife Emma, and their 22 month old son Francis.  

Matt, Emma, and I, featuring a block of parmesan cheese. Matt and Emma are big cheese people - some might even argue that Emma's family is the first family in cheese.

Francis doing his best baby Yoda impression in one of Emma's old sweaters. Over the past few months, Matt and Emma have enjoyed seeing Francis develop a sense of humor and outlandish facial expressions. So far, the consensus seems to be that he's more like Emma than Matt so far. Francis's favorite word is agua and he's a big fan of bikes. 

Matt, Emma, and Francis recently moved back to the Midwest after 6 years in the Bay Area, where Matt completed his PhD.  Matt is originally from the northern Chicago suburbs. He recently started a new job as an economics professor - he’s teaching a handful of courses related to behavioral economics this semester. Much of his research to date has been related to sports betting - and his dissertation even got a recent write up in the Wall Street Journal. 

Ahead of his first day of teaching, Matt gave me a tour of UChicago. They've got some great gothic architecture, a Frank Lloyd Wright house (not pictured - for some reason I opted not to take a photo of this), and some nice water features. Matt gave his first two lectures while I was in Chicago - as may be expected, he said #2 was much easier than #1. 

Like her sister Maggie, Emma is originally from Sheboygan, WI. She’s an accountant and was able to stay with the same firm when moving to Chicago. The past few months have been particularly busy for her as she’s navigated handing off all her California clients and worked to develop her credibility with her new coworkers and clients while a few key teammates have been out on parental leave.  

While you may not be able to tell from the seated photo, both Matt and Emma are quite tall and talented at basketball. And basketball (along with mutual friends that worked tirelessly) was one of the first things that brought them together. Matt sought to assemble a dream team capable of winning the coed intramural championship and recruited Emma - the rest is history. Assembling this dream team came at a cost though, as myself and a couple other shorter friends were cut from the team to make room for the "more talented" newcomers. In response to being cut from the team, I attempted to assemble a team capable of challenging Matt’s for the title. Needless to say, my efforts fell short in all respects, as we were annihilated by Matt's team and I also didn't find my future wife.  

The view from Promontory Point - just across the road from where Matt, Emma, and Francis now live in Hyde Park. Definitely one of the most scenic places I've run on this trip. 

The move back to the Midwest has been a welcome change for Matt and Emma - they’re now much closer to family, which has been a big help with child care, but they’re definitely looking forward to reconnecting with their friends from the Bay Area at a friend’s wedding in Germany next summer that will serve as a defacto grad school reunion.  

I also caught up with a handful of other friends from college in Chicago.

I forgot to take a picture with Johnny while in Chicago, so here's an old one. I'm realizing this photo must be 5+ years old as I'm cleanshaven and have short hair. Johnny has since decided to shave his head, so if you picture PittBull, you're not far off from what he looks like now. 

After touring UChicago with Matt, I met up with my old Cleveland roommate Johnny for lunch. Johnny grew up near Allentown, PA (he played against Saquon Barkley in high school sports). We met at Notre Dame because we were in the same major and interned at the same company. After graduating, we both ended up getting jobs in Cleveland and ended up working at the same company for most of the past 5 years. Unlike me, Johnny knew going into college he didn’t want to be an engineer but figured it would be a useful degree. He moved to Chicago a few years back to pursue a part time MBA while working full time. He left his job a few weeks before I did this spring, but for a new opportunity in consulting, not a motorcycle trip. Since then he's probably covered more miles than I have, but in my defense, planes go faster than motorcycles. 

So far he’s loving consulting, but the stop and start nature of consulting projects has made it difficult to invest in relationships and his golf game as much as he’d like to. He recently won tickets to the Ryder cup at a golf tournament he played in, and he said the national team/patriot element of the Ryder cup made for a unique atmosphere he hasn’t seen elsewhere in golf. 

We tried a glass of wine cask aged whiskey he picked up on a recent trip to Ireland before he had to leave to catch a flight to his next client. 

The view from Johnny's apartment. Key features are the view of the Kenzie Street Bridge where Dave Matthews Band tour bus once dumped 800 lbs of sewage on a Chicago architectural tour boat passing beneath. Since my visit, Johnny has moved across the street as his current building tried to raise the rent exorbitantly - a constant struggle in the city.   

After lunch with Johnny, I got a professional beard trim (don’t worry they took minimal length off, mostly just fluff) as I had to look my best for my brother’s wedding the following weekend. I then stopped over at the lakeshore before scratching my itch for deep dish pizza by meeting my friend Brendan at Lou Malnati’s.  

Chicago utilizes it's lakefront much better than Cleveland.

If I recall correctly, Brendan and I met through the dorm soccer team in college. Back in college, Brendan tried to walk onto the ND football team and was having a solid tryout until they asked him to switch from his natural position of receiver to defensive back - suffice to say they were not impressed with his footwork in defensive back drills he had never done before. 

Brendan is originally from New York and worked on Wall Street for a few years after school before moving to Chicago about 3 years ago. What started out as a casual curiosity about cryptocurrency eventually turned into a job as he now works for a company that is developing new technology for crypto wallets and crypto contracts. 

Outside of work, Roche serves as the commissioner of (one of) my fantasy football leagues (he’s in 3 of his own) and he recently got married. Similar to Matt and Emma, Brendan and his wife Isabella got to know each other well through intramural sports in college - maybe if I had been better at basketball, I’d be married my now.  

The next morning, I met my friend Elizabeth for coffee. I can’t recall exactly how I met Elizabeth, but I do recall that her and her sister Jasmine were some of my earliest friends at Notre Dame. 

Elizabeth is originally from Chicago and enjoys being there to see her younger brother who is now in high school grow up. She works in accounting and recently moved from a more customer facing role to a project management role. While there’s a lot to learn, she’s excited to spend more of her time working on longer term strategic initiatives and less on putting out fires. Another positive of the new role is that once she completes project management training, she’ll continue working with coworkers on the accounting teams that she already has strong rapport with. 

I like to call this the Fake Sears Tower as I somehow always mistake it for the real one. 

Some interesting sculptures near Millenium Station.

A bee farm in downtown Chicago - I think I can now say I've seen it all

After coffee, I walked around a Navy Pier - which surprisingly was a ghost town - before walking out to West Loop to meet my friend Mark for a some Italian beef and a beer. 

The real Sears (Willis?) Tower - as seen from my walk to the West Loop

Death, Taxes, and Canadian Geese - The only constants in America

View from Navy Pier

They were trying to charge $20 to ride the Ferris wheel at Navy Pier - it appears that everyone else at Navy Pier that day agreed with me that that was way to much

A big old anchor from the USS Chicago

Gotta say, I'm always surprised by how pretty of a city Chicago is

The mustache is new, but Mark's wife, Grace, is a fan of it, so he said it may stay a while

Mark is originally from Cincinnati and actually went to high school with one of my old coworkers (shout out to Sneha). After undergrad, Mark went to med school in Madison, WI and moved to Chicago about a year and a half ago to start his residency in anesthesiology. His wife, Grace, who was unable to join us due to work, also went to ND undergrad and UW for med school - she is currently an OBGYN resident. Unlike all the other Chicago couples I’ve discussed here, they did not play intramural basketball together (to the best of my knowledge) - instead, they met while studying abroad in Pueblo, Mexico. They've kept up their international travel with a recent trip to France. While it will be a number of years before they complete residency and have a choice about where to live, Mark said they’re enjoying Chicago and could potentially see living there long term.  

A surreal moment watching a tour boat pass under the Kenzie Street Bridge

After lunch with Mark, I walked back to the River North to enjoy sunset on the riverwalk.  While there, I couldn’t resist stopping at the preeminent Taco Bell in downtown Chicago on Whacker Ave.  

Not sure what was going on with the lights and the camera, but could not seem to avoid the glare. Taco Bell Chicago went with darker, more industrial styling with some colorful graffiti highlights. 

Taco Bell Chicago had the cleanest restroom I've seen

Food: I got the Cantina Chicken Taco. If I recall correctly, it was solid - good serving portions.

Staff: Limited interactions, but they were friendly and helpful when I asked for the bathroom key.

Facilities: By far the cleanest restroom I've seen at any Taco Bell, buuutttt that may have been because it's locked/requires a key and thus gets limited use. They also didn't have any toilet paper (or even a toilet paper holder?) in the stall, so minus points for that. Guess you have to go to the sink to get toilet paper? Maybe they plan to put in a bidet? Who knows?

Atmosphere: Taco Bell Whacker Ave in Chicago certainly had a cool, minimalist underground vibe. Can't remember the playlist though. 

After that I made the obligatory tourist walks to the Bean and through millennium Park, which was being set up for the Chicago Marathon. 

Show me a better Bean photo - I'll wait

Bet you've never seen a photo of the underside of the Bean

In Chicago, I may have done as much walking as I did on my big hiking days in Michigan and Minnesota: 12+ miles on day 1 and 15+ on day 2. While my legs were a bit worn out after all that walking, I’d still argue it’s the best way to see and get to know a city - especially one as pretty as Chicago. That, and I need to get my walking stamina up before I head to Patagonia in December. 

More to Come, 

KTrain