Known all over the world for its architecture, transportation infrastructure, and sheer determination, Chicago is the kind of city that’s easy to fall in love with. My first flirtation with urbanism, density, and rail service, Chicago was my hub city growing up. I have fond memories of taking the bus to Union Station to find a train. Though the magic of Chicago in snowy winter will always keep me captivated, I blew into town as the Lollapalooza crowd arrived and we were blessed with unseasonably temperate weather. I was fortunate enough to spend part of my time in town with my Coordinator Joe Aiello, a local boy who loves the city that raised him. We put in miles and miles of walking, bussing, and riding the rails all over. Every time I visit this city, I find new reasons to want to stay longer.

The last time I was in Chicago, Union Station was very much under construction. The Great Hall is now looking beautifully restored. From the replacement of the warped marble steps to the replacement of the ceiling, I am extremely impressed with the diligence of those working on this massive undertaking. I met with Derrick James who I had not seen since my Amtrak cookout in D.C. Though in truth, it was just a few months ago, it felt like I hadn’t seen him in ages. I was roadweary and probably smelled as awful as I looked, he embraced me with open arms and toured me around one of my most favorite places. I was impressed by how the lounges, conference rooms, waiting hall, and platforms have been updated and tuned to meet the needs of today’s commuters and travelers. One thing that really stood out to me is still undergoing renovations to the old lunch counter. Destroyed in the 80’s by fire, it is going to be restored and will play host to a variety of local vendors. Once again, we’re seeing the food hall resurgence being strategically backed by a large city with larger appetites and I completely support it.

After dropping my bags at the St. Clair Hotel, I made my way to Au Chevel to grab a beer with another local, Joe Szabo Former Federal Railroad Administrator under our last President and longtime supporter of Rail Passengers Association. While we sipped our brews and had a good laugh at the Happy Hour Homemade Bologna Sandwich, I asked him what he sees as the next steps for our transit based future. Much like the other leaders of his generation, he emphasized the need for millennial and Gen Z engagement. Through the last century so much about rail culture and commuter culture has changed. People have fought for desegregation, rural accessibility, and connectivity of our smaller towns to urban city centers. We commiserate the idealism of car culture, the debt trap associated with it and the false sense of individualism it creates while simultaneously causing irreparable damage to the planet we need to survive. Szabo gave me hope that with clear paths, good leadership, transparency, and grassroots organizing, we can continue building the infrastructure our changing demographics demand.

As the sun rose the following morning, I headed to Lou Mitchell’s. This diner is sacred and time honored. I was welcomed by the family with the customary donut hole and ushered to a nice cozy booth in the back. It’s a spot in town where I have taken refuge on long layovers before. Lou Mitchell’s is known for consistent execution, bottomless coffee, and large servings. I smashed the spinach and feta omelette with Greek sausage and a good 5 cups of coffee while Joe Aiello and I planned out our day. First up was a meeting with Rick Harnish, followed by a CTA tour and Chicago dogs for dinner.

As I took the brown line over to Rick’s office, I read up on the proposed Midwest High Speed Rail and was pleasantly surprised to see Louisville, Kentucky as a city they want to bring into the fold. I have spent countless hours making the trek many Kentuckians have – first finding a ride to Louisville, then a bus to Chicago then a train to the rest of the country. As stated in “A Market-Based Model to High-Speed Rail” Harnish advocates for reconnecting rural areas. 

“In many parts of the Midwest, long drives are understood to be a necessary part of daily life. Whether for work, shopping, or to see friends, a car can be the only way to get around. The rising cost of gas and the hidden costs of vehicle maintenance make this reality more expensive than most of us realize: the annual cost of vehicle ownership in the Midwest is nearly $10,000. 

Although Amtrak serves more than 200 stations around the Midwest, most have only one train a day. High-speed rail would mean faster and more frequent service to all of these towns. If scheduled properly, the trains could serve as long-distance commuter trains, giving residents greater access to employment opportunities. Adding direct connections to major airports will create an essential link to international markets. 

Fast, modern trains give everyone — employees, tourists, customers, friends, and family — greater choices of where to live, work, visit and spend their money. Meanwhile, businesses enjoy a larger market and new opportunities for investment. Innovation and productivity increases more trips become possible. Everyone benefits.”

As Rick elaborated on Midwest high-speed rail propositions, I found that his take was not idealistic. It is something that has been done in other countries, for instance, France, Germany, Spain and Japan each provide examples of designing and building modern passenger rail network for a similar crowd. By utilizing trains optimized for speed, regional express, super commuter, and attaching to existing services, we could see multifaceted solutions for different types of service needed by different types of passengers. After my discussions with Rick I think the best way for Rail Passengers Association to assist with this is by building a stronger coalition working together. 

A unified cross jurisdictional planning effort would unite these disperse constituencies into a strong coalition, capable of securing federal and state funds. The result would be a rail line allowing higher speeds and much more frequent service for a variety of trains. It would lower overall cost yet produce a greater impact as an integrated whole rather than individual projects.

The other element of this is high frequency connecting services. We would need intercity buses, regional rail routes, and transit systems in place throughout the Midwest that provide frequent service to strategically placed high-speed rail platforms. Once again highlighting how multi-modal accessibility can lead to an overall superior outcome in transitioning to rail for commuter and long distance services.

As we concluded a day packed full of education, camaraderie, and train talks, I was ready for a hearty meal. This came in the form of a Chicago dog from the Weiner Circle. Complete with neon green relish, sport pepper, seeded bun and too many fries, Joe Aiello and I tucked into to one his hometown foods. We hypothesized what would come next for Chicago’s rail service as the shiny metal above ground system whipped by glistening in the distance.

We strolled around trying to walk off the bazillion calories each dog contains and marveled at the beauty of high-art high-density, glass and light which surrounded us. The architectural beauty of the city juxtaposed with the cash-only hot dog stand held a certain kind of magic. A city that contains so many stories and only so many ways to get there. After we parted ways, I headed up to my hotel to turn off the lights and let the city shine through my window with its gold gilded comfort still twinkling through the night. 

My next day began bright and early. As the lollapalooza crowd had taken the city hostage, we boarded the Hiawatha and headed north to a place I had never experienced – Milwaukee, Wisconsin. Yes, I did tuck another day trip into my already packed 50 day adventure. 

Arriving to the Intermodal station just before 10am, I was eager to meet with Alderman Bauman and learn about the HOP. Not only is it a free streetcar service planning to expand, it’s gorgeous. I was offered a tour of the facilities and found that every element of the HOP service was maintained with excellence. It was clear to me that this community valued their streetcar service and as I looked over the proposed expansion routes, I was met with excitement and smiles galore. Not only does this make it easier for tourists visiting the bustling downtown and brewery districts, it will keep the roads safer for those who rely on cars. Free public transportation helps reduce DUIs, reduces passenger miles on highways, and in the winter provides safe means to and from work, commerce, and home. Overall, this is a big win for Milwaukee.

Alderman Bauman and I enjoyed lunch at the Milwaukee Public Market, a multi-vendor food hall championing a variety of local foods, beer, crafts, and gifts. The two floor venue is extremely versatile and well-loved by the people of the city. I was surprised by the variety of cuisine offered. Having never been to Wisconsin, I didn’t really know what to expect and I am glad to have gone without expectation. We sampled a selection of east coast oysters, fish tacos, and sandwiches from St Paul Fish Co.

My last item for the day was a stroll from downtown to Old World Third to meet up with a reporter from Urban Milwaukee. We congregated at Brüdd and shared a selection of local cheese from the adjacent cheese shop, paired with Spotted Cow beer. I was fascinated by the all-femme team that abandoned the boys club of Chicago to distribute in state only. It’s real power move and the power of their draft matches. From the classic sharp cheddar to the heady blue, I saw how the cheese capital came to earn its name, every bite was absolute heaven.

Before hopping on the Southwest Chief to embark on the second half of the trip, I met up with Joe for lunch. He insisted I had one more Chicago tradition I had to try. It was a massive undertaking, calorically dense, with serious instruction and one of the most satisfying foods I’ve experienced thus far. The hot dipped Italian beef. It is a legendary sandwich and though I’ve had variations, the original can not be beat. 

A hot messy source of pure joy, you really do have to lean and commit to this beast. We rushed to Portillo’s on the southside to smash before I had to dash. Paired with a goblet of beer, peppers and drenched in au jus, it is piles of shaved roast beef wrapped in a not too sweet but plenty spongy Italian-style roll. Now that I’ve experienced it, I completely understand why it’s frequently the top rated sandwich in the States. If you’ve never had one, you’ve never lived. Health and longevity be damned, this is an essential life experience for any foodie. As I said farewell to my host and ran through Chicago’s Union Station combatting the meat sweats, I looked upon the hall one last time.

Though I have spent a fair amount of time in this station, it’s always the hardest to leave. While I live to travel and often say I will return to a number of my favorite destinations, Chicago still holds my heart in so many unmanifested ways. No matter my age or the weather, the light shining off of this beautiful city as it fades into the horizon is always a sweet nostalgic goodbye.

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  • Lynn Aldrich says:

    I only lived in Chicago for 6 months, but it’s my favorite city. Each time i travel through Chicago on Amtrak I get a short visit. I go walking over to the bean and experience a taste of the city once again.

  • The Gnome says:

    Even though I lived in the Midwest growing up and had been to Chicago several times, I only had my first Chicago dog when traveling through the city via Amtrak this spring. The station is truly marvelous!