Based on many of the criteria people tend to look at when determining their ideal location, Chicago would not be an ideal place for me. The winters are too cold, and extended periods of consistent cold are frequent. It’s not too uncommon for 2-3 weeks to go by without temperatures rising above freezing. There are also very few good places for outdoor activities near Chicago. Most of the area within a four hour drive of Chicago is flat farmland. The few interesting places in the area, like Starved Rock and the Wisconsin Dells, end up being quite crowded on nice weekend days. Finally, Chicago seems to not only tolerate, but sometimes celebrate its’ corrupt politics. Alderman go to jail on a regular basis, and so do governors. This culture has lead to an offensively high sales tax. When people asked me why Illinois seems obsessed with Abraham Lincoln, I would often joke about the state having to honor its’ last non-corrupt politician.

Preferences on these kinds of issues are amongst the most common questions asked in your standard online “what city is right for you” quiz. Had I decided on where to live based on these online quizes, I probably would have never even considered living in Chicago. But, I really did enjoy my time here. So, as I visited Chicago and saw my friends and such this past weekend, I thought about what it is about Chicago that I really enjoyed, and what keeps people moving here.

One thing I certainly learned is that one’s impression of a place is dependent not only on how good of a fit that place is for them, but also on circumstances. It is quite possible for someone to move to a place that seems ideal for them, but be in a bad situation (bad job, bad economy, bad relationship), and end up with a negative impression. Likewise, some of the flaws a location may have could be overlooked or tolerated by someone who has really satisfying situation. For most of my four years in Chicago, I enjoyed a good job, a functional relationship, and a really great social situation. All of this made that additional sales tax, the cold week in February, and having to drive three hours for a decent hike feel like less of an annoyance.

I also learned that sometimes there are other factors that have a major impact on one’s satisfaction in their hometown that is not considered when choosing a place to relocate to, and also not considered in your standard “what city is right for you” quiz. For example, Chicago has a great energy to it. I really did fit well in the pace of life here; fast, but maybe not quite as fast as the east coast. There are tons of different neighborhoods, with different vibes, allowing people to have a lot of different kinds of experiences on a day-to-day basis without traveling far. Many different kinds of people can find a place that suits them all within Chicago’s city limits. Chicago also has one of the best food scenes in the country, with regionally distinct food that ranges from the traditionally “blue collar” Chicago-style hot dog and italian beef sandwiches to fancy restaurants like Alinea and Girl and Goat.

If I take a step back, and look at a more high-level overview of the situation, I think the main lesion to be taken away is that some situations that sound less than ideal deserve a chance. Because, well, you never know what you will discover and come to love about them. This applied to me in the city of Chicago, but could also apply to a job, a relationship, or involvement in some other kind of organization. When deciding where to live, who to date, what job to take, etc. we often think about, at most 5-10 factors, while our satisfaction with the situation can be even more dependent on factors we typically fail to consider. I did not expect to find the vibrant social scene that I found at the job I had in Chicago, and I hear many people discuss aspects of their significant others that they had originally overlooked, but have come to really enjoy.

For the last couple of decades, Chicago’s population has been somewhat balanced by an influx of people from elsewhere in the midwest that counteracts a loss of people to the south and southwest. Michigan and Ohio seem to produce the most Chicago transplants, as their economies have been weak the last couple of decades. I actually recall a time when I felt like I was unable to go more than a week without somehow setting foot in a Michigan State bar. This has changed the nature of the city significantly, with many neighborhoods on the north and northwest sides gentrifying, and some traditional middle class neighborhoods elsewhere in the city emptying out.

There is not shortage of debate online regarding Chicago’s future. One can find particularly intense debates on websites such as city-data and the urbanophile. Here I have read all kinds of opinions, ranging from imminent decline to Chicago becoming the next world class city. On one hand, there does appear to be a danger that Chicago could experience a decline if the influx of people from other midwestern states, particularly Michigan and Ohio were to dry up, as those states are beginning to show signs of life. However, I find it hard to believe that the young professional community would stop particularly seeking out Chicago for what it has to offer with regards to jobs and lifestyle. Not only does Chicago offer nearly all that New York offers at a fraction of the price, but it also offers a nice compromise with regards to pace of life and work intensity. In New York, work-life is quite stressful, and people end up working extra hours. The West Coast is very casual, and slower in pace. Chicago offers a nice compromise between the two. I have heard a lot of people in Chicago tell me that New York would be “too much” for them. Many of these people could be either frustrated, or unable to find their ideal job in a smaller city. If one can think of of place as offering a specific product, there is still a demand out there for the “product” that Chicago is offering. In that sense, Chicago’s main danger in the future would be another city (perhaps Minneapolis, Denver, or even Omaha) offering that same product at a lower cost.