So often the places we visit become fixed in our minds in a certain instant. No matter how often I go back to them, I’ll associate Madison with early childhood, Washington D.C. with college, Minneapolis with grad school; I see Mexico City is a 20-year-old, and New York as a teenager. There’s an exception to the rule, though: I go to Chicago often enough, and for diverse enough reasons, that I see the city through different eyes, over and over again. It’s home to one side of my family, a tourist and business destination, and a waystation on journeys across the country. I’ve never lived there and likely never will, but Chicago has become a central city within my life, a crossroads for travels both literal and metaphorical.

As a young child, Chicago was a frequent destination for family visits and cultural enrichment, and one of the few places outside of Minnesota or Wisconsin my family ever went unless someone else was paying. My early elementary school writings included a memorable lament about the traffic on the Eisenhower Expressway. I also have fond memories of the city’s excellent museums the view from the top of the then-Sears Tower when it was the tallest building in the world. (The Willis Tower, somehow diminished with a new name that accompanied the decline of its former namesake, no longer cracks a worldwide top 20.) As a child, Chicago was big, gaudy, and also a bit scary. I remember my parents always switching drivers at the Elgin toll on I-90 because my dad, who otherwise did all the driving, wanted nothing to do with Chicago traffic. I also recall my parents locking the doors and rolling up the windows even as we drove through certain neighborhoods, something we sure as hell didn’t need to do in Duluth or in Edgerton, Wisconsin.

Later, the trips into the mess of the city decreased, or at least seemed to in my mind; our visits instead came to consist of long meanders by car through suburban subdivisions, an exercise that always left me exhausted and peevish. Perhaps my inner urban planner was born on these journeys. These annoyances found their counterbalance in baseball, my favorite teenage diversion. The bleachers at Wrigley were always the highlight of any trip to Chicago, where I somehow always managed to catch memorable games, like the 90-some degree game with the Mets that at the time set the record for longest nine-inning game, Roger Clemens’ failed crack at a 300^th win, or the game in which the Cubs lost when a ball bounced off the top of Aramis Ramirez’s head. But I’d settle for the White Sox as well, and this most recent visit reminded me what a delight it is to be in a place that actually cares about one of my favorite sports. (Sorry, Twins fans: the difference in passion is night and day.)

In my undergraduate days, I’d often have a layover in Chicago as I made my Amtrak journey from Minnesota to DC and back. Sometimes I’d try to connect with family or high school friends who went to college in the Windy City, but sometimes I’d just wander it myself, meander down to Buckingham Fountain or pass out on an outdoor bench beside the Art Institute. In this era, another side of the city opened up to me: hangouts in Wicker Park or Pilsen, those neighborhoods that were once ethnic enclaves but are now getting overwhelmed by those awful young white professionals who like elaborate food and urban living. And as I came to recognize the importance of family in my own life, the allure of the strong ties I have in that city pushed aside any grumpiness over long drives.

My urban planning education painted Chicago in a completely different light. Machine politics, racism that sometimes called worse than that in the South, Robert Taylor Homes and Cabrini-Green: the hubris that stuffing poor people like sardines into projects would somehow improve their condition, and the perhaps even greater conceit that knocking down all those projects with no follow-up plan would somehow make it all better. Chicago is perhaps the most American of cities, emblematic of both remarkable wealth and beauty and misery and squalor, all living side by side. Nowadays, its politics of the past century look more like a predictor of the future instead of some relic from a bygone era.

On my most recent visit, I came on business for the first time, and had a window into Chicago as the financial capital of the Midwest. I marched down downtown streets in a suit, the capable guide for those in my traveling party less familiar with the city. I passed through security checks and up elevators in towers with magnificent views, and schmoozed in a box at a baseball game and over dinners and drinks paid for by other people’s corporate cards. Suddenly, Chicago was a world of opportunity that put old Duluth to shame. As I basked along the Riverwalk during a break between meetings, I was consumed by a rush of rightness, a sense that I’d made it that I hadn’t felt since my early days at Georgetown. An insatiable ambition was, momentarily, appeased.

I know I tend to come off as a diehard Duluthian, of being as deeply committed to my city as anything in my life. But it would be a lie to say I don’t waver, and waver often. Part of me could be very happy in Chicago, and at my core I’m probably more at ease in Logan Square or Oak Park than I am in small towns. But I am, maybe paradoxically, most content in a place where I can easily inhabit both extremes, and any number of places in between. I experience the world far too vividly to cut off any edges in pursuit of comfort. I’m a lover of cities and people, but they are still just one side of a whole. The hellacious traffic, lack of topography, and relative lack of green space in Chicago—or even relatively convenient escapes to large areas of green space—would grate on me in time. And while I have family there, my connections for work purposes aren’t exactly robust.

But the visits to Chicago will continue, with three more slated for this year alone. It will continue to inspire, confound, and shed new light on different stages of life. It will always be a home away from home.